2433:
60:
493:
318:
2978:, is the only name for a primary amine retained as a preferred IUPAC name for which full substitution is permitted on the ring and the nitrogen atom. It is a Type 2a retained name; for the rules of substitution see P-15.1.8.2. Substitution is limited to substituent groups cited as prefixes in accordance with the seniority of functional groups explicitly expressed or implied in the functional parent compound name. The name benzenamine may be used in general nomenclature.
1895:
1059:
834:
1734:
1617:
844:
1493:
839:
829:
824:
2024:
1817:
1055:
4310:
70:
2482:
1060:
1317:
2494:
acid (GAA, essentially distilled vinegar) in a 50:50 solution. GAA is a much safer, less reactive acid. This single combined reagent is relatively stable over time. A single spot or line applied to the pileus (or other surface). In my experience the newer formulation works as well as
Schaffer's while being safer and more convenient."
3997:: 186 – 196. (Note: In the case of a metal having two or more distinct oxides (e.g., iron), a "protosalt" is an obsolete term for a salt that is obtained from the oxide containing the lowest proportion of oxygen to metal; e.g., in the case of iron, which has two oxides – iron (II) oxide (FeO) and iron (III) oxide (Fe
2493:
Aniline oil is also used for mushroom identification. Kerrigan's 2016 Agaricus of North
America P45: (Referring to Schaffer's reaction) "In fact I recommend switching to the following modified test. Frank (1988) developed an alternative formulation in which aniline oil is combined with glacial acetic
3442:
Westerhaus, Felix A.; Jagadeesh, Rajenahally V.; Wienhöfer, Gerrit; Pohl, Marga-Martina; Radnik, Jörg; Surkus, Annette-Enrica; Rabeah, Jabor; Junge, Kathrin; Junge, Henrik; Nielsen, Martin; Brückner, Angelika; Beller, Matthias (2013). "Heterogenized Cobalt Oxide
Catalysts for Nitroarene Reduction by
3900:
N. Zinin (1842). "Beschreibung einiger neuer organischer Basen, dargestellt durch die
Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure" (Description of some new organic bases, produced by the action of hydrogen sulfide on compounds of hydrocarbons
1583:
Consistent with these factors, substituted anilines with electron donating groups are more pyramidalized, while those with electron withdrawing groups are more planar. In the parent aniline, the lone pair is approximately 12% s character, corresponding to sp hybridization. (For comparison,
1058:
2019:
Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp carbon and resonance effects, as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring. (see the picture below):
1575:
substituent. The observed geometry reflects a compromise between two competing factors: 1) stabilization of the N lone pair in an orbital with significant s character favors pyramidalization (orbitals with s character are lower in energy), while 2)
2922:
pathway was also activated, its activity was not sufficient to prevent the accumulation of 8-OHdG. The accumulation of oxidative DNA damages in the spleen following exposure to aniline may increase mutagenic events that underlie tumorigenesis.
1447:: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Aniline can be diazotized to give a
3428:
852:
804:
4065:
1076:
3376:
Alabugin I. V.; Manoharan, M.; Buck, M.; Clark, R. J. Substituted
Anilines: The Tug-Of-War between Pyramidalization and Resonance Inside and Outside of Crystal Cavities. THEOCHEM, 2007, 813, 21-27.
3870:: 453–457. In a postscript to this article, Erdmann (one of the journal's editors) argues that aniline and the "cristallin", which was found by Unverdorben in 1826, are the same substance; see
2730:, not yet recognized as a bacterium, was still thought to be a parasite, and medical bacteriologists, believing that bacteria were not susceptible to the chemotherapeutic approach, overlooked
1567:. The nitrogen is described as having high p character. The amino group in aniline is flatter (i.e., it is a "shallower pyramid") than that in an aliphatic amine, owing to conjugation of the
1745:
The oxidation of aniline has been heavily investigated, and can result in reactions localized at nitrogen or more commonly results in the formation of new C-N bonds. In alkaline solution,
974:
2353:, which is known as "ice cold mixture" because the temperature for the reaction was as low as 0.5 °C. The benzene diazonium salt is formed as major product alongside the byproducts
1653:
In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and
3056:
3004:
1201:
1330:
1705:, and many others. They also are usually prepared by nitration of the substituted aromatic compounds followed by reduction. For example, this approach is used to convert
3911:"Beschreibung einiger neuer organischer Basen, dargestellt durch die Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure"
2027:
The lone electron pair on the nitrogen delocalizes into the pi system of the benzene ring. This is responsible for nitrogen's weaker basicity compared to other amines.
1061:
3363:
2419:
Aniline is predominantly used for the preparation of methylenedianiline and related compounds by condensation with formaldehyde. The diamines are condensed with
1580:
of the N lone pair into the aryl ring favors planarity (a lone pair in a pure p orbital gives the best overlap with the orbitals of the benzene ring π system).
3130:
Kahl, Thomas; Schröder, K. W.; Lawrence, F. R.; Elvers, Barbara; Höke, Hartmut; Pfefferkorn, R.; Marshall, W. J. (2007). "Aniline". In
Ullmann, Fritz (ed.).
542:
4330:
2872:
1587:
The pyramidalization angle between the C–N bond and the bisector of the H–N–H angle is 142.5°. For comparison, in more strongly pyramidal amine group in
1611:: Approximately 4B kg are produced annually. Catalysts include nickel, copper, palladium, and platinum, and newer catalysts continue to be discovered.
3987:"De l'action des protosels de fer sur la nitronaphtaline et la nitrobenzine. Nouvelle méthode de formation des bases organiques artificielles de Zinin"
3921:(1): 140–153. Benzidam is named on page 150. Fritzsche, Zinin's colleague, soon recognized that "benzidam" was actually aniline. See: Fritzsche (1842)
970:
2644:
Factory), now the largest chemical supplier, echoes the legacy of the synthetic dye industry, built via aniline dyes and extended via the related
1083:
3276:
G. M. Wójcik "Structural
Chemistry of Anilines" in Anilines (Patai's Chemistry of Functional Groups), S. Patai, Ed. 2007, Wiley-VCH, Weinheim.
1717:. Alternatively, using Buchwald-Hartwig coupling or Ullmann reaction approaches, aryl halides can be aminated with aqueous or gaseous ammonia.
753:
4117:
3609:
3515:
3339:
3149:
2959:
3175:"Electron conjugation versus π-π repulsion in substituted benzenes: why the carbon-nitrogen bond in nitrobenzene is longer than in aniline"
1725:
The chemistry of aniline is rich because the compound has been cheaply available for many years. Below are some classes of its reactions.
2859:, igniting on contact between fuel and oxidizer. It is also dense, and can be stored for extended periods. Aniline was later replaced by
1440:
3426:, Heinrich, Sperber; Guenter, Poehler & Joachim, Pistor Hans et al., "Production of aniline", issued 1964-06-09
4407:
4325:
3664:
2276:
59:
4402:
3727:
3579:
3399:
3311:
3027:
2876:
507:
3230:"On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems"
3989:(On the action of iron protosalts on nitronaphthaline and nitrobenzene. New method of forming Zinin's synthetic organic bases.),
2907:
2424:
785:
4044:
4019:
954:
2035:. Aniline is, for example, more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution.
922:
962:
912:
428:
1010:
838:
833:
1898:
Aniline can react with bromine even in room temperatures in water. Acetyl chloride is added to prevent tribromination.
946:
471:
2620:. At the time of mauveine's discovery, aniline was expensive. Soon thereafter, applying a method reported in 1854 by
1026:
2345:
amine into diazonium salt is called diazotisation. In this reaction primary aromatic amine is allowed to react with
1069:
843:
4397:
4354:
2943:
2911:
2593:
2569:
1837:
1337:
1225:
1212:
668:
2432:
4412:
2557:
2519:
325:
3799:
F. F. Runge (1834) "Ueber einige
Produkte der Steinkohlendestillation" (On some products of coal distillation),
2883:), and it has specifically been linked to bladder cancer. Aniline has been implicated as one possible cause of
2597:
2507:
2384:
Being a standard reagent in laboratories, aniline is used for many niche reactions. Its acetate is used in the
1106:
31:
1741:, a colorless liquid when pure, illustrating the tendency of anilines to air-oxidize to dark-colored products.
900:
2185:
of 193–195 °C and 192 °C, respectively. These derivatives are of importance in the color industry.
4243:(1995), R. J. Flanagan, S. S. Brown, F. A. de Wolff, R. A. Braithwaite, B. Widdop: World Health Organization
3657:
Epoxy Resins
Technology Handbook (Manufacturing Process, Synthesis, Epoxy Resin Adhesives and Epoxy Coatings
2702:
2687:
2552:
990:
697:
4229:
Forest
Decline: Cause-Effect Research in the United States of North America and Federal Republic of Germany
978:
823:
313:
2820:
1778:
1738:
1682:
3965:
3599:
2374:
2856:
2539:
1884:
1564:
1544:
866:
828:
816:
101:
4372:
3553:
1563:
in anilines is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between
3495:
1014:
255:
3774:
3452:
3241:
3186:
2919:
2385:
1496:
982:
89:
3228:
Raczyńska, Ewa D.; Hallman, Małgorzata; Kolczyńska, Katarzyna; Stępniewski, Tomasz M. (2010-07-12).
3945:"Organische Salzbasen, aus Nitronaphtalose und Nitrobenzid mittelst Schwefelwasserstoff entstehend"
2828:
2114:
1577:
1417:
1353:
1299:
938:
488:
132:
4231:. Germany: Assessment Group for Biology, Ecology and Energy of the Julich Nuclear Research Center.
4127:
3820:
1894:
1844:, which enhances the electron-donating ability of the ring. For example, reaction of aniline with
185:
4348:
3976:: 37–87. On page 48, Hofmann argues that krystallin, kyanol, benzidam, and aniline are identical.
3709:
3476:
3357:
2795:, chemotherapy of wide effectiveness, propelled the American pharmaceutics industry. In 1939, at
2727:
2605:
2437:
2404:
2308:
1993:
1540:
1448:
1436:
readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
930:
215:
2906:
response. Rats exposed to aniline in drinking water, showed a significant increase in oxidative
2707:
2621:
1632:
994:
926:
203:
3751:
Kerrigan, Richard (2016). Agaricus of North America. NYBG Press. p. 45. ISBN 978-0-89327-536-5.
3731:
942:
4387:
4287:
4210:
4104:
4087:
3944:
3930:
3910:
3871:
3859:
3812:
3762:
3701:
3660:
3630:
3605:
3575:
3511:
3468:
3405:
3395:
3345:
3335:
3307:
3259:
3210:
3202:
3155:
3145:
3023:
2955:
2796:
2758:
2731:
2686:. During the first decade of the 20th century, while trying to modify synthetic dyes to treat
2625:
2350:
2342:
1794:
1698:
1636:
1500:
958:
4256:
Ma, Huaxian; Wang, Jianling; Abdel-Rahman, Sherif Z.; Boor, Paul J.; Khan, M. Firoze (2008).
4187:
Tanaka, Takuji; Miyazawa, Katsuhito; Tsukamoto, Testuya; Kuno, Toshiya; Suzuki, Koji (2011).
3808:
2940:
Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1428:, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten
4277:
4269:
4258:"Oxidative DNA damage and its repair in rat spleen following subchronic exposure to aniline"
4200:
3833:
3782:
3693:
3503:
3460:
3299:
3277:
3249:
3194:
3137:
2947:
2848:
2641:
2527:
2503:
2455:
2329:
2194:
1981:
1888:
1758:
1492:
1455:
1369:
1365:
710:
647:
570:
178:
69:
2779:
azo dyes – already with an expired patent, synthesized in 1908 in Vienna by the researcher
1616:
998:
444:
437:
4122:
3986:
3567:
2467:
2408:
2378:
2358:
2107:
2054:
1849:
1714:
1548:
1517:
1279:
1267:
1263:
1119:
1002:
966:
344:
275:
4362:
3947:(Organic bases originating from nitronaphthalene and nitrobenzene via hydrogen sulfide),
2871:
Aniline is toxic by inhalation of the vapour, ingestion, or percutaneous absorption. The
986:
149:
3778:
3456:
3245:
3190:
1733:
1631:). The reduction of nitrobenzene to aniline was also performed as part of reductions by
1018:
492:
317:
235:
142:
4358:, vol. 2 (9th ed.), New York: Charles Scribner's Sons, pp. 47–48 short=x
4282:
4257:
2884:
2746:
2649:
2543:
2346:
2312:
2272:
2217:
2103:
1985:
1903:
1654:
1647:
1628:
1413:
1308:
1283:
1257:
918:
658:
2454:(2%), and dyes and pigments (2%). As additives to rubber, aniline derivatives such as
2023:
1816:
1439:
Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in
4392:
4381:
4321:
4316:
2816:
2800:
2772:
2750:
2459:
2339:
2182:
2050:
1906:
is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline.
1876:
1845:
1802:
1798:
1770:
1710:
1694:
1624:
1604:
1525:
1421:
739:
636:
626:
449:
401:
306:
154:
3713:
3377:
1034:
892:
4149:
3886:
3480:
2903:
2844:
2808:
2788:
2696:
2691:
2679:
2561:
2334:
2268:
1910:
1782:
1754:
1750:
1702:
1666:
1425:
1387:
1287:
934:
880:
735:
3423:
3281:
1685:
of aniline are known where the phenyl group is further substituted. These include
3847:
J. Fritzsche (1840) "Ueber das Anilin, ein neues Zersetzungsproduct des Indigo",
3131:
950:
396:
389:
3625:
3595:
3507:
3070:
2951:
2852:
2667:
2463:
2397:
2084:. At high temperatures aniline and carboxylic acids react to give the anilides.
2081:
1964:
1880:
1820:
1810:
1790:
1588:
1560:
1466:
1402:
1187:
1169:
1143:
1095:
4273:
2628:
enabled the evolution of a massive dye industry in Germany. Today, the name of
4367:
4006:
3303:
3000:
2812:
2804:
2784:
2780:
2735:
2671:
2511:
2486:
2471:
2296:
1909:
The largest scale industrial reaction of aniline involves its alkylation with
1806:
1786:
1746:
1433:
595:
266:
4020:"Proceedings of Chemical Societies: Chemical Society, Thursday, May 16, 1861"
3786:
3705:
3349:
3263:
3206:
3141:
3929:: 352. Reprinted as a postscript to Zinin's article in: J. Fritzsche (1842)
3409:
3174:
3159:
3048:
2860:
2776:
2754:
2723:
2675:
2656:
2451:
2370:
2233:
2032:
1989:
1774:
1686:
1662:
1658:
1592:
1568:
1470:
729:
460:
17:
4291:
4214:
3472:
3214:
896:
4205:
4188:
3095:
1451:
salt, which can then undergo various nucleophilic substitution reactions.
904:
876:
4334:, vol. 2 (11th ed.), Cambridge University Press, pp. 47–48
3332:
Stereoelectronic effects : a bridge between structure and reactivity
2719:
2683:
2617:
2613:
2601:
2523:
2470:). The principal use of aniline in the dye industry is as a precursor to
2420:
2389:
2280:
2198:
2099:
1766:
1762:
1690:
1670:
1608:
1584:
alkylamines generally have lone pairs in orbitals that are close to sp.)
1513:
1477:
1082:
1075:
1068:
1041:
884:
286:
42:
4347:
3296:
Amino, Nitrosco and Nitro Compounds and Their Derivatives: Vol. 1 (1982)
2481:
295:
3765:[On the behaviour of organic substances at high temperatures].
3697:
3464:
3254:
3229:
3198:
2898:
Exposure of rats to aniline can elicit a response that is toxic to the
2840:
2824:
2767:
2762:
2715:
2645:
2609:
2589:
2462:, are antioxidants. Illustrative of the drugs prepared from aniline is
2304:
2288:
2062:
2044:
1841:
1706:
1521:
1476:
Because an early source of the benzene from which they are derived was
616:
376:
326:
38:
3680:
Jung, Woo-Hyuk; Ha, Eun-Ju; Chung, Il doo; Lee, Jang-Oo (2008-08-01).
1639:). These stoichiometric routes remain useful for specialty anilines.
3966:"Chemische Untersuchung der organischen Basen im Steinkohlen-Theeröl"
3681:
2899:
2823:
in 1939, was the first antibiotic, yet its toxicity restricted it to
2711:
2447:
2321:
2279:. Through these intermediates, the amine group can be converted to a
1833:
1643:
246:
3763:"Ueber das Verhalten der organischen Körper in höheren Temperaturen"
3173:
Zhang, Huaiyu; Jiang, Xiaoyu; Wu, Wei; Mo, Yirong (April 28, 2016).
2403:
In addition, aniline is the starting component in the production of
1307:
Except where otherwise noted, data are given for materials in their
4005:) – FeO is the "protoxide" from which protosalts can be made. See:
3682:"Synthesis of aniline-based azopolymers for surface relief grating"
2753:
a red azo dye, introduced in 1935 as the first antibacterial drug,
2572:
showed that these were all the same substance, known thereafter as
364:
4315:
This article incorporates text from a publication now in the
3096:"aniline | Etymology, origin and meaning of aniline by etymonline"
2742:
2637:
2480:
2475:
2431:
2354:
2058:
2022:
1893:
1815:
1732:
1491:
1444:
872:
412:
226:
184:
177:
167:
4101:
The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine
1022:
3601:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
2629:
1623:
The reduction of nitrobenzene to aniline was first performed by
1572:
1531:
1429:
1238:
1030:
888:
355:
1424:
synthesis. Its main use is in the manufacture of precursors to
2915:
2831:
introduced the chemotherapeutic approach to cancer treatment.
2393:
2325:
1813:. These polymers exhibit rich redox and acid-base properties.
3659:(2nd ed.). Asia Pacific Business Press Inc. p. 38.
3053:
Immediately Dangerous to Life or Health Concentrations (IDLH)
1006:
476:
68:
58:
3968:(Chemical investigation of organic bases in coal tar oil),
3860:"Ueber das Anilin, ein neues Zersetzungsproduct des Indigo"
3834:"Ueber das Anilin, ein neues Zersetzungsproduct des Indigo"
1765:, in the presence of certain metallic salts (especially of
2783:
for his doctoral research. By the 1940s, over 500 related
3536:
3534:
3532:
2666:
In the late 19th century, derivatives of aniline such as
2388:
for carbohydrates, identifying pentoses by conversion to
1053:
2706:
approach to medicine – failed and switched to modifying
2267:
Aniline and its ring-substituted derivatives react with
1988:
such as aniline are, in general, much weaker bases than
1607:(typically at 200–300 °C) in the presence of metal
1591:, this value is ~125°, while that of the amine group in
2803:
developed Fleming's penicillin into the first systemic
1887:
is formed. To generate the mono-substituted product, a
1642:
Aniline can alternatively be prepared from ammonia and
1325:
3394:(7th ed.). Boston: McGraw-Hill Higher Education.
2061:. The amides formed from aniline are sometimes called
1840:
reactions. Its high reactivity reflects that it is an
3931:"Bemerkung zu vorstehender Abhandlung des Hrn. Zinin"
3836:(On aniline, a new decomposition product of indigo),
3057:
National Institute for Occupational Safety and Health
3005:
National Institute for Occupational Safety and Health
2526:
that turned a beautiful blue color when treated with
1992:
amines. Aniline reacts with strong acids to form the
1828:
Electrophilic reactions at ortho- and para- positions
4189:"Pathobiology and Chemoprevention of Bladder Cancer"
2604:. Mauveine quickly became a commercial dye. Other
4056:Wilcox RW, "The treatment of influenza in adults",
4024:
The Chemical News and Journal of Industrial Science
2718:drug, and serendipitously obtained a treatment for
27:
Organic compound (C₆H₅NH₂); simplest aromatic amine
2910:to the spleen, detected as a 2.8-fold increase in
3933:(Comment on the preceding article by Mr. Zinin),
2890:Many methods exist for the detection of aniline.
2787:were produced. Medications in high demand during
1753:produces the violet-coloring matter violaniline.
202:
4227:Krahl-Urban, B., Papke, H.E., Peters, K. (1988)
4177:. 10th ed. (1983), p.96, Rahway: Merck & Co.
4150:http://www.nuclear-weapons.info/cde.htm#Corporal
3650:
3648:
3502:, John Wiley & Sons, Ltd, pp. 455–481,
3378:http://dx.doi.org/10.1016/j.theochem.2007.02.016
2031:Missing in such an analysis is consideration of
1836:, aniline derivatives are highly susceptible to
1773:. Hydrochloric acid and potassium chlorate give
1516:, compared to the C−N bond length of 1.47 Å for
395:
388:
2311:. This diazonium salt can also be reacted with
1420:, as well as a versatile starting material for
1057:
641:184.13 °C (363.43 °F; 457.28 K)
148:
141:
3730:. The Chemical Market Reporter. Archived from
3604:(6th ed.), New York: Wiley-Interscience,
3133:Ullmann's encyclopedia of industrial chemistry
2436:Most aniline is consumed in the production of
3909:(18): 272–285. Reprinted in: N. Zinin (1842)
3891:, ultimately from Sanskrit "nīla", dark-blue.
3443:Pyrolysis of Molecularly Defined Complexes".
3022:(8th ed.). W. H. Freeman. p. 1031.
1469:, although less so than structurally similar
631:−6.30 °C (20.66 °F; 266.85 K)
8:
3554:"Aniline synthesis by amination (Arylation)"
3294:Sorriso, S. (1982). "Structural chemistry".
3077:. US NOAA Office of Response and Restoration
2775:– a colorless intermediate for many, highly
2181:-dimethylaniline are colorless liquids with
4368:CDC - NIOSH Pocket Guide to Chemical Hazrds
4165:, The Royal Institute of Chemistry, London.
4103:(New York: Oxford University Press, 2007),
2726:– the first successful chemotherapy agent.
4078:
4076:
4074:
3362:: CS1 maint: location missing publisher (
1963:The resulting diamine is the precursor to
1875:If bromine water is added to aniline, the
1114:770 °C (1,420 °F; 1,040 K)
491:
316:
274:
47:
4281:
4251:
4249:
4204:
3253:
3125:
3123:
3121:
3119:
3117:
3115:
2839:Some early American rockets, such as the
2799:, seeking an alternative to sulfa drugs,
2745:sought medical applications of its dyes.
1524:between C(aryl) and N. The length of the
1443:reactions. Likewise, it is also prone to
516:InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
443:
436:
3540:
2999:NIOSH Pocket Guide to Chemical Hazards.
2550:, after an indigo-yielding plant, anil (
2315:
2255:
2251:
2247:
2243:
2239:
2227:
2223:
2212:
2208:
2204:
2162:
2158:
2154:
2150:
2146:
2142:
2138:
2134:
2130:
2076:
2072:
2068:
2003:
1999:
1955:
1951:
1947:
1943:
1939:
1935:
1931:
1927:
1923:
1919:
1867:
1863:
1859:
1855:
1535:
1512:In aniline, the C−N bond length is 1.41
1408:
1397:
1393:
1382:
1378:
1374:
586:
582:
578:
526:InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
4363:International Chemical Safety Card 0011
2931:
2369:It reacts with nitrobenzene to produce
2216:), which may be decomposed into phenyl
1603:Industrial aniline production involves
547:
512:
487:
294:
37:Not to be confused with the amino acid
3355:
3043:
3041:
3039:
2994:
2992:
2990:
2988:
2986:
2678:drugs, with their cardiac-suppressive
2502:Aniline was first isolated in 1826 by
1635:in 1854, using iron as the reductant (
1364:indicating a derived substance) is an
307:
4035:Auerbach G, "Azo and naphthol dyes",
3325:
3323:
2197:, it gives sulfocarbanilide (diphenyl
1793:; in acid solution to aniline black.
1454:Like other amines, aniline is both a
1100:70 °C (158 °F; 343 K)
519:Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-N
254:
234:
7:
3574:(3rd ed.), Belmont: Wadsworth,
3496:"The Zinin Reduction of Nitroarenes"
3018:Vollhardt, P.; Schore, Neil (2018).
2912:8-hydroxy-2'-deoxyguanosine (8-OHdG)
2734:'s report in 1928 on the effects of
2624:, it was prepared "by the ton". The
2588:In 1856, while trying to synthesise
2427:, a precursor to urethane polymers.
1416:. It is an industrially significant
4262:Toxicology and Applied Pharmacology
4018:Perkin, William Henry. 1861-06-08.
3179:Physical Chemistry Chemical Physics
2855:as an oxidizer. The combination is
1823:can form upon oxidation of aniline.
1781:in neutral solution oxidizes it to
1661:, which contains aniline and ortho-
1543:. The C−N bond length is 1.34 Å in
1539:in anilines is highly sensitive to
1441:electrophilic aromatic substitution
529:Key: PAYRUJLWNCNPSJ-UHFFFAOYAP
379:
363:
4163:Hazards in the Chemical Laboratory
2728:Salvarsan's targeted microorganism
2564:and obtained a base that he named
2546:and obtained an oil that he named
2277:benzenediazonium tetrafluoroborate
1913:. An idealized equation is shown:
1891:with acetyl chloride is required:
799:potential occupational carcinogen
25:
3849:Justus Liebigs Annalen der Chemie
2489:, which is prepared from aniline.
4308:
3991:Annales de Chemie et de Physique
3970:Annalen der Chemie und Pharmacie
3949:Annalen der Chemie und Pharmacie
2847:, used a mixture of aniline and
2634:Badische Anilin- und Soda-Fabrik
2542:(1808–1871) treated indigo with
1615:
1315:
842:
837:
832:
827:
822:
2881:Probably carcinogenic to humans
2440:, a precursor to polyurethanes.
2425:methylene diphenyl diisocyanate
1480:, aniline dyes are also called
1311:(at 25 °C , 100 kPa).
3964:August Wilhelm Hofmann (1843)
2944:The Royal Society of Chemistry
2411:is the other main ingredient.
2102:at elevated temperatures over
1627:in 1842, using sulfide salts (
786:Occupational safety and health
1:
4373:Aniline electropolymerisation
4126:. 15 May 1950. Archived from
3935:Journal für praktische Chemie
3915:Journal für praktische Chemie
3864:Journal für praktische Chemie
3844:(12): 161–165. Reprinted in:
3801:Annalen der Physik und Chemie
3767:Annalen der Physik und Chemie
3282:10.1002/9780470682531.pat0385
2392:. It is used to stain neural
2338:. The reaction of converting
2098:-Methylation of aniline with
1206:(US health exposure limits):
1158:400 mg/kg (guinea pig, oral)
63:Structural formula of aniline
2189:Carbon disulfide derivatives
1879:is decolourised and a white
4346:Baynes, T. S., ed. (1878),
4241:Basic Analytical Toxicology
3508:10.1002/0471264180.or020.04
2952:10.1039/9781849733069-FP001
2946:. 2014. pp. 416, 668.
2450:processing chemicals (9%),
1967:and related diisocyanates.
1677:Related aniline derivatives
1412:), aniline is the simplest
1132:or concentration (LD, LC):
54:
4429:
4274:10.1016/j.taap.2008.08.010
4086:(Houten: Springer, 2009),
4026:. Retrieved on 2007-09-24.
3390:Carey, Francis A. (2008).
3330:Alabugin, Igor V. (2016).
2827:use.) After World War II,
2694:– who had coined the term
2654:
2570:August Wilhelm von Hofmann
2522:isolated a substance from
2042:
1838:electrophilic substitution
1785:; in alkaline solution to
1360: 'indigo shrub', and
36:
29:
4408:IARC Group 2A carcinogens
4118:"Medicine: Spoils of War"
3943:See also: (Anon.) (1842)
3761:Otto Unverdorben (1826).
3640:, vol. 1, p. 82
3304:10.1002/9780470771662.ch1
2688:African sleeping sickness
2558:Nikolay Nikolaevich Zinin
1996:(or phenylammonium) ion (
1665:and is obtained from the
1305:
1298:
1293:
1249:
1200:
1128:
803:
783:
778:
746:
563:
538:
503:
125:
112:
100:
88:
83:
53:
4403:Hazardous air pollutants
3787:10.1002/andp.18260841109
3142:10.1002/14356007.a02_303
2662:Developments in medicine
2648:. The first azo dye was
2508:destructive distillation
1848:at 180 °C produces
1294:Supplementary data page
913:Precautionary statements
653:3.6 g/(100 mL) at 20 °C
32:Aniline (disambiguation)
4355:Encyclopædia Britannica
4331:Encyclopædia Britannica
4084:The History of Oncology
3901:and hyponitric acid ),
3686:Macromolecular Research
3075:cameochemicals.noaa.gov
2791:(1939–45), these first
2608:dyes followed, such as
2553:Indigofera suffruticosa
1154:464 mg/kg (mouse, oral)
698:Magnetic susceptibility
684:4.63 (conjugate acid; H
3494:Porter, H. K. (2011),
2867:Toxicology and testing
2584:Synthetic dye industry
2490:
2441:
2377:. Hydrogenation gives
2332:, in a process called
2028:
1899:
1824:
1779:Potassium permanganate
1742:
1739:2,6-diisopropylaniline
1657:; and aniline oil for
1595:has an angle of 180°.
1504:
1064:
663:0.6 mmHg (20 °C)
74:
64:
4161:Muir, GD (ed.) 1971,
4148:Brian Burnell. 2016.
4007:Wiktionary: protosalt
3923:Bulletin Scientifique
3903:Bulletin Scientifique
3838:Bulletin Scientifique
3624:Carl N. Webb (1941).
2821:Rockefeller Institute
2682:often countered with
2655:Further information:
2540:Carl Julius Fritzsche
2484:
2435:
2026:
1971:Reactions at nitrogen
1902:The reaction to form
1897:
1885:2,4,6-tribromoaniline
1819:
1809:affords a variety of
1736:
1545:2,4,6-trinitroaniline
1520:, indicating partial
1495:
1219:TWA 5 ppm (19 mg/m)
1176:175 ppm (mouse, 7 h)
1156:440 mg/kg (rat, oral)
1152:250 mg/kg (rat, oral)
1150:195 mg/kg (dog, oral)
1063:
102:Systematic IUPAC name
72:
62:
3858:J. Fritzsche (1840)
3832:J. Fritzsche (1840)
3655:Panda, Dr H (2019).
2920:base excision repair
2894:Oxidative DNA damage
2714:, the first organic
2598:William Henry Perkin
2386:aniline acetate test
2049:Aniline reacts with
1709:into toluidines and
1499:of aniline from the
1497:Ball-and-stick model
1170:median concentration
1046:(fire diamond)
90:Preferred IUPAC name
30:For other uses, see
4206:10.1155/2011/528353
4193:Journal of Oncology
3779:1826AnP....84..397U
3594:Smith, Michael B.;
3457:2013NatCh...5..537W
3246:2010Symm....2.1485R
3191:2016PCCP...1811821Z
3185:(17): 11821–11828.
3136:. Wiley: New York.
2829:Cornelius P. Rhoads
2446:Other uses include
2309:Sandmeyer reactions
2173:-Methylaniline and
1681:Many analogues and
1541:substituent effects
1300:Aniline (data page)
1196:180 ppm (cat, 8 h)
648:Solubility in water
603: g·mol
216:Beilstein Reference
50:
3985:A. Béchamp (1854)
3698:10.1007/BF03218555
3465:10.1038/nchem.1645
3334:. Chichester, UK.
3255:10.3390/sym2031485
3199:10.1039/c6cp00471g
3100:www.etymonline.com
2491:
2442:
2438:methylenedianiline
2405:diglycidyl aniline
2275:. One example is
2029:
1980:Aniline is a weak
1900:
1825:
1743:
1699:aminobenzoic acids
1669:(échappés) of the
1505:
1418:commodity chemical
1386:. Consisting of a
1338:Infobox references
1250:Related compounds
1241:(Immediate danger)
1194:250 ppm (rat, 4 h)
1065:
75:
65:
48:
4398:German inventions
3638:Collected Volumes
3631:Organic Syntheses
3611:978-0-471-72091-1
3572:Organic Chemistry
3517:978-0-471-26418-7
3500:Organic Reactions
3392:Organic chemistry
3341:978-1-118-90637-8
3298:. pp. 1–51.
3151:978-3-527-20138-9
3020:Organic Chemistry
2961:978-0-85404-182-4
2797:Oxford University
2759:Pasteur Institute
2749:identified as an
2732:Alexander Fleming
2626:Béchamp reduction
2456:phenylenediamines
2375:Wohl–Aue reaction
2232:), and triphenyl
1805:. Oxidation with
1795:Hypochlorous acid
1757:converts it into
1749:results, whereas
1646:derived from the
1637:Bechamp reduction
1501:crystal structure
1401:) attached to an
1346:Chemical compound
1344:
1343:
1275:Related compounds
867:Hazard statements
704:−62.95·10 cm/mol
611:Colorless liquid
472:CompTox Dashboard
186:Interactive image
179:Interactive image
79:
78:
16:(Redirected from
4420:
4413:Phenyl compounds
4359:
4351:
4335:
4314:
4312:
4311:
4296:
4295:
4285:
4253:
4244:
4238:
4232:
4225:
4219:
4218:
4208:
4184:
4178:
4172:
4166:
4159:
4153:
4146:
4140:
4139:
4137:
4135:
4114:
4108:
4097:
4091:
4082:D J Th Wagener,
4080:
4069:
4054:
4048:
4037:Textile Colorist
4033:
4027:
4016:
4010:
3983:
3977:
3962:
3956:
3898:
3892:
3883:
3877:
3830:
3824:
3797:
3791:
3790:
3758:
3752:
3749:
3743:
3742:
3740:
3739:
3724:
3718:
3717:
3677:
3671:
3670:
3652:
3643:
3641:
3634:
3621:
3615:
3614:
3591:
3585:
3584:
3568:McMurry, John E.
3564:
3558:
3557:
3550:
3544:
3538:
3527:
3526:
3525:
3524:
3491:
3485:
3484:
3445:Nature Chemistry
3439:
3433:
3432:
3431:
3427:
3420:
3414:
3413:
3387:
3381:
3374:
3368:
3367:
3361:
3353:
3327:
3318:
3317:
3291:
3285:
3274:
3268:
3267:
3257:
3240:(3): 1485–1509.
3225:
3219:
3218:
3170:
3164:
3163:
3127:
3110:
3109:
3107:
3106:
3092:
3086:
3085:
3083:
3082:
3067:
3061:
3060:
3045:
3034:
3033:
3015:
3009:
3008:
2996:
2981:
2980:
2936:
2851:as a fuel, with
2849:furfuryl alcohol
2757:, soon found at
2528:chloride of lime
2504:Otto Unverdorben
2466:(acetaminophen,
2330:benzeneazophenol
2318:
2302:
2294:
2286:
2258:
2231:
2215:
2195:carbon disulfide
2166:
2122:-dimethylaniline
2079:
2015:
2014:
2013:
2010:
1959:
1871:
1619:
1555:Pyramidalization
1538:
1508:Aryl-N distances
1411:
1400:
1385:
1366:organic compound
1328:
1322:
1319:
1318:
1188:lowest published
1144:lowest published
1120:Explosive limits
1085:
1078:
1071:
1056:
1036:
1032:
1028:
1024:
1020:
1016:
1012:
1008:
1004:
1000:
996:
992:
988:
984:
980:
976:
972:
968:
964:
960:
956:
952:
948:
944:
940:
936:
932:
928:
924:
920:
906:
902:
898:
894:
890:
886:
882:
878:
874:
846:
841:
836:
831:
826:
770:
747:Thermochemistry
711:Refractive index
602:
589:
571:Chemical formula
496:
495:
480:
478:
447:
440:
399:
392:
381:
367:
345:Gmelin Reference
328:
320:
309:
298:
278:
258:
238:
206:
188:
181:
152:
145:
55:
51:
21:
4428:
4427:
4423:
4422:
4421:
4419:
4418:
4417:
4378:
4377:
4349:"Aniline"
4345:
4342:
4324:, ed. (1911), "
4320:
4309:
4307:
4304:
4299:
4255:
4254:
4247:
4239:
4235:
4226:
4222:
4186:
4185:
4181:
4175:The Merck Index
4173:
4169:
4160:
4156:
4147:
4143:
4133:
4131:
4130:on 24 June 2013
4116:
4115:
4111:
4098:
4094:
4081:
4072:
4055:
4051:
4034:
4030:
4017:
4013:
4004:
4000:
3984:
3980:
3963:
3959:
3942:
3899:
3895:
3884:
3880:
3831:
3827:
3823:(see page 331).
3811:(see page 65),
3798:
3794:
3773:(11): 397–410.
3760:
3759:
3755:
3750:
3746:
3737:
3735:
3726:
3725:
3721:
3679:
3678:
3674:
3667:
3654:
3653:
3646:
3636:
3623:
3622:
3618:
3612:
3593:
3592:
3588:
3582:
3566:
3565:
3561:
3552:
3551:
3547:
3539:
3530:
3522:
3520:
3518:
3493:
3492:
3488:
3441:
3440:
3436:
3429:
3422:
3421:
3417:
3402:
3389:
3388:
3384:
3375:
3371:
3354:
3342:
3329:
3328:
3321:
3314:
3293:
3292:
3288:
3275:
3271:
3227:
3226:
3222:
3172:
3171:
3167:
3152:
3129:
3128:
3113:
3104:
3102:
3094:
3093:
3089:
3080:
3078:
3069:
3068:
3064:
3047:
3046:
3037:
3030:
3017:
3016:
3012:
2998:
2997:
2984:
2977:
2973:
2969:
2962:
2938:
2937:
2933:
2929:
2918:. Although the
2896:
2869:
2837:
2815:, developed by
2664:
2659:
2622:Antoine Béchamp
2586:
2520:Friedlieb Runge
2514:. He called it
2500:
2417:
2409:Epichlorohydrin
2379:cyclohexylamine
2367:
2365:Other reactions
2359:sodium chloride
2349:and 2 moles of
2317:
2313:
2303:, where X is a
2300:
2292:
2284:
2273:diazonium salts
2265:
2257:
2253:
2249:
2245:
2241:
2237:
2229:
2225:
2221:
2214:
2210:
2206:
2202:
2191:
2164:
2160:
2156:
2152:
2148:
2144:
2140:
2136:
2132:
2128:
2093:
2078:
2074:
2070:
2066:
2055:acetyl chloride
2047:
2041:
2011:
2008:
2007:
2005:
2001:
1997:
1986:Aromatic amines
1978:
1973:
1957:
1953:
1949:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1869:
1865:
1861:
1857:
1853:
1850:sulfanilic acid
1830:
1801:and para-amino
1789:, ammonia, and
1731:
1723:
1715:4-chloroaniline
1679:
1655:para-toluidines
1633:Antoine Béchamp
1601:
1557:
1549:3-methylaniline
1537:
1529:
1518:cyclohexylamine
1510:
1490:
1464:
1410:
1406:
1399:
1395:
1391:
1384:
1380:
1376:
1372:
1347:
1340:
1335:
1334:
1333: ?)
1324:
1320:
1316:
1312:
1286:
1282:
1280:Phenylhydrazine
1276:
1268:2-Naphthylamine
1266:
1264:1-Naphthylamine
1260:
1258:aromatic amines
1242:
1229:
1216:
1195:
1191:
1185:
1173:
1167:
1157:
1155:
1153:
1151:
1147:
1141:
1111:
1108:
1090:
1089:
1088:
1087:
1080:
1073:
1066:
1062:
1054:
915:
869:
855:
819:
796:
771:
768:
762:
758:
755:
754:Std enthalpy of
742:at 25 °C)
721:
719:
701:
691:
687:
677:
650:
600:
588:
584:
580:
576:
573:
559:
556:
551:
546:
545:
534:
531:
530:
527:
521:
520:
517:
511:
510:
499:
481:
474:
455:
423:
407:
382:
370:
347:
338:
301:
281:
261:
241:
218:
209:
191:
171:
160:
135:
121:
120:
118:
116:
108:
107:
96:
95:
46:
35:
28:
23:
22:
15:
12:
11:
5:
4426:
4424:
4416:
4415:
4410:
4405:
4400:
4395:
4390:
4380:
4379:
4376:
4375:
4370:
4365:
4360:
4341:
4340:External links
4338:
4337:
4336:
4322:Chisholm, Hugh
4303:
4300:
4298:
4297:
4268:(2): 247–253.
4245:
4233:
4220:
4179:
4167:
4154:
4141:
4109:
4099:John E Lesch,
4092:
4070:
4060:, 1900 Dec 15;
4049:
4028:
4011:
4002:
3998:
3993:, 3rd series,
3978:
3957:
3893:
3878:
3876:
3875:
3856:
3825:
3792:
3753:
3744:
3719:
3692:(6): 532–538.
3672:
3666:978-8178331829
3665:
3644:
3616:
3610:
3586:
3580:
3559:
3545:
3528:
3516:
3486:
3451:(6): 537–543.
3434:
3415:
3400:
3382:
3369:
3340:
3319:
3312:
3286:
3269:
3220:
3165:
3150:
3111:
3087:
3062:
3035:
3028:
3010:
2982:
2975:
2971:
2967:
2966:Aniline, for C
2960:
2930:
2928:
2925:
2902:, including a
2895:
2892:
2885:forest dieback
2868:
2865:
2836:
2833:
2747:Gerhard Domagk
2663:
2660:
2650:aniline yellow
2585:
2582:
2544:caustic potash
2530:. He named it
2499:
2496:
2474:, the blue of
2444:
2443:
2416:
2413:
2366:
2363:
2347:sodium nitrite
2264:
2261:
2218:isothiocyanate
2190:
2187:
2183:boiling points
2168:
2167:
2111:-methylaniline
2104:acid catalysts
2092:
2086:
2065:, for example
2051:acyl chlorides
2043:Main article:
2040:
2037:
1977:
1974:
1972:
1969:
1961:
1960:
1904:4-bromoaniline
1829:
1826:
1730:
1727:
1722:
1719:
1695:chloroanilines
1678:
1675:
1648:cumene process
1629:Zinin reaction
1621:
1620:
1600:
1597:
1578:delocalization
1556:
1553:
1509:
1506:
1489:
1486:
1462:
1414:aromatic amine
1345:
1342:
1341:
1336:
1314:
1313:
1309:standard state
1306:
1303:
1302:
1296:
1295:
1291:
1290:
1284:Nitrosobenzene
1277:
1274:
1271:
1270:
1261:
1255:
1252:
1251:
1247:
1246:
1243:
1237:
1234:
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1098:
1092:
1091:
1081:
1074:
1067:
1052:
1051:
1050:
1049:
1047:
1038:
1037:
975:P305+P351+P338
916:
911:
908:
907:
870:
865:
862:
861:
856:
851:
848:
847:
820:
815:
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659:Vapor pressure
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26:
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10:
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4:
3:
2:
4425:
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4357:
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4350:
4344:
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4339:
4333:
4332:
4327:
4323:
4318:
4317:public domain
4306:
4305:
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4293:
4289:
4284:
4279:
4275:
4271:
4267:
4263:
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3961:
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3950:
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3940:
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3924:
3920:
3916:
3912:
3908:
3904:
3897:
3894:
3890:
3889:
3882:
3879:
3873:
3872:pages 457–459
3869:
3865:
3861:
3857:
3854:
3850:
3846:
3845:
3843:
3839:
3835:
3829:
3826:
3822:
3818:
3814:
3810:
3806:
3802:
3796:
3793:
3788:
3784:
3780:
3776:
3772:
3768:
3764:
3757:
3754:
3748:
3745:
3734:on 2002-02-19
3733:
3729:
3723:
3720:
3715:
3711:
3707:
3703:
3699:
3695:
3691:
3687:
3683:
3676:
3673:
3668:
3662:
3658:
3651:
3649:
3645:
3639:
3633:
3632:
3627:
3626:"Benzanilide"
3620:
3617:
3613:
3607:
3603:
3602:
3597:
3590:
3587:
3583:
3581:0-534-16218-5
3577:
3573:
3569:
3563:
3560:
3555:
3549:
3546:
3543:, p. 48.
3542:
3541:Chisholm 1911
3537:
3535:
3533:
3529:
3519:
3513:
3509:
3505:
3501:
3497:
3490:
3487:
3482:
3478:
3474:
3470:
3466:
3462:
3458:
3454:
3450:
3446:
3438:
3435:
3425:
3419:
3416:
3411:
3407:
3403:
3401:9780073047874
3397:
3393:
3386:
3383:
3379:
3373:
3370:
3365:
3359:
3351:
3347:
3343:
3337:
3333:
3326:
3324:
3320:
3315:
3313:9780470771662
3309:
3305:
3301:
3297:
3290:
3287:
3283:
3279:
3273:
3270:
3265:
3261:
3256:
3251:
3247:
3243:
3239:
3235:
3231:
3224:
3221:
3216:
3212:
3208:
3204:
3200:
3196:
3192:
3188:
3184:
3180:
3176:
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3161:
3157:
3153:
3147:
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3139:
3135:
3134:
3126:
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3120:
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3116:
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3097:
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3076:
3072:
3066:
3063:
3058:
3054:
3050:
3044:
3042:
3040:
3036:
3031:
3029:9781319079451
3025:
3021:
3014:
3011:
3006:
3002:
2995:
2993:
2991:
2989:
2987:
2983:
2979:
2963:
2957:
2953:
2949:
2945:
2942:. Cambridge:
2941:
2935:
2932:
2926:
2924:
2921:
2917:
2913:
2909:
2905:
2901:
2893:
2891:
2888:
2886:
2882:
2878:
2874:
2866:
2864:
2862:
2858:
2854:
2850:
2846:
2842:
2834:
2832:
2830:
2826:
2822:
2818:
2814:
2810:
2806:
2802:
2801:Howard Florey
2798:
2794:
2793:miracle drugs
2790:
2786:
2782:
2778:
2774:
2773:sulfanilamide
2770:
2769:
2764:
2760:
2756:
2752:
2751:antibacterial
2748:
2744:
2739:
2737:
2733:
2729:
2725:
2721:
2717:
2713:
2709:
2705:
2704:
2699:
2698:
2693:
2689:
2685:
2681:
2677:
2673:
2669:
2661:
2658:
2653:
2651:
2647:
2643:
2639:
2635:
2632:, originally
2631:
2627:
2623:
2619:
2615:
2611:
2607:
2603:
2599:
2595:
2591:
2583:
2581:
2579:
2575:
2571:
2567:
2563:
2559:
2555:
2554:
2549:
2545:
2541:
2537:
2533:
2529:
2525:
2521:
2517:
2513:
2509:
2505:
2497:
2495:
2488:
2483:
2479:
2477:
2473:
2469:
2465:
2461:
2460:diphenylamine
2457:
2453:
2449:
2439:
2434:
2430:
2429:
2428:
2426:
2422:
2414:
2412:
2410:
2406:
2401:
2399:
2395:
2391:
2387:
2382:
2380:
2376:
2372:
2364:
2362:
2360:
2356:
2352:
2348:
2344:
2341:
2337:
2336:
2331:
2327:
2324:to produce a
2323:
2319:
2310:
2306:
2298:
2290:
2282:
2278:
2274:
2270:
2263:Diazotization
2262:
2260:
2235:
2219:
2200:
2196:
2188:
2186:
2184:
2180:
2176:
2172:
2127:
2126:
2125:
2123:
2121:
2117:
2112:
2110:
2105:
2101:
2097:
2090:
2087:
2085:
2083:
2064:
2060:
2056:
2052:
2046:
2038:
2036:
2034:
2025:
2021:
2017:
1995:
1991:
1987:
1983:
1975:
1970:
1968:
1966:
1916:
1915:
1914:
1912:
1907:
1905:
1896:
1892:
1890:
1886:
1882:
1878:
1877:bromine water
1873:
1851:
1847:
1846:sulfuric acid
1843:
1839:
1835:
1827:
1822:
1818:
1814:
1812:
1808:
1804:
1803:diphenylamine
1800:
1799:4-aminophenol
1796:
1792:
1788:
1784:
1780:
1776:
1772:
1771:aniline black
1768:
1764:
1760:
1756:
1752:
1748:
1740:
1735:
1728:
1726:
1720:
1718:
1716:
1712:
1711:chlorobenzene
1708:
1704:
1703:nitroanilines
1700:
1696:
1692:
1688:
1684:
1676:
1674:
1672:
1668:
1664:
1660:
1656:
1651:
1649:
1645:
1640:
1638:
1634:
1630:
1626:
1625:Nikolay Zinin
1618:
1614:
1613:
1612:
1610:
1606:
1598:
1596:
1594:
1590:
1585:
1581:
1579:
1574:
1570:
1566:
1562:
1554:
1552:
1550:
1547:vs 1.44 Å in
1546:
1542:
1533:
1527:
1526:chemical bond
1523:
1519:
1515:
1507:
1502:
1498:
1494:
1487:
1485:
1483:
1482:coal tar dyes
1479:
1474:
1472:
1468:
1465:= 4.6) and a
1461:
1457:
1452:
1450:
1446:
1442:
1437:
1435:
1431:
1427:
1423:
1422:fine chemical
1419:
1415:
1404:
1389:
1371:
1367:
1363:
1359:
1355:
1351:
1339:
1332:
1327:
1310:
1304:
1301:
1297:
1292:
1289:
1285:
1281:
1278:
1273:
1272:
1269:
1265:
1262:
1259:
1254:
1253:
1248:
1244:
1240:
1236:
1235:
1231:
1228:(Recommended)
1227:
1223:
1222:
1218:
1215:(Permissible)
1214:
1210:
1209:
1205:
1204:
1199:
1193:
1189:
1180:
1179:
1175:
1171:
1162:
1161:
1149:
1145:
1136:
1135:
1131:
1127:
1123:
1121:
1118:
1117:
1113:
1110:
1104:
1103:
1099:
1097:
1094:
1093:
1086:
1079:
1072:
1048:
1045:
1044:
1040:
1039:
917:
914:
910:
909:
871:
868:
864:
863:
860:
857:
854:
850:
849:
845:
840:
835:
830:
825:
821:
818:
814:
813:
809:
807:
802:
798:
793:
792:
788:
787:
782:
777:
774:−3394 kJ/mol
773:
765:
757:
751:
750:
745:
741:
737:
733:
731:
728:
727:
723:
716:
712:
708:
707:
703:
699:
695:
694:
683:
682:
680:
674:
670:
667:
666:
662:
660:
657:
656:
652:
649:
645:
644:
640:
638:
637:Boiling point
635:
634:
630:
628:
627:Melting point
625:
624:
620:
618:
615:
614:
610:
607:
606:
599:
597:
594:
593:
575:
572:
568:
567:
562:
553:
548:
544:
537:
523:
513:
509:
502:
494:
490:
489:DTXSID8020090
486:
485:
483:
473:
469:
468:
464:
462:
459:
458:
451:
446:
442:
439:
435:
434:
432:
430:
427:
426:
419:
418:
416:
414:
411:
410:
403:
398:
394:
391:
387:
386:
384:
378:
374:
373:
366:
362:
361:
359:
357:
354:
353:
349:
346:
342:
341:
334:
333:
331:
329:
324:
323:
319:
315:
312:
310:
308:ECHA InfoCard
305:
304:
297:
293:
292:
290:
288:
285:
284:
277:
273:
272:
270:
268:
265:
264:
257:
253:
252:
250:
248:
245:
244:
237:
233:
232:
230:
228:
225:
224:
220:
217:
213:
212:
205:
201:
200:
198:
195:
194:
187:
183:
180:
176:
175:
173:
169:
164:
163:
156:
151:
147:
144:
140:
139:
137:
134:
130:
129:
124:
111:
103:
99:
91:
87:
82:
71:
67:
61:
57:
56:
52:
44:
40:
33:
19:
4353:
4329:
4265:
4261:
4240:
4236:
4228:
4223:
4196:
4192:
4182:
4174:
4170:
4162:
4157:
4144:
4132:. Retrieved
4128:the original
4121:
4112:
4100:
4095:
4083:
4061:
4058:Medical News
4057:
4052:
4043:(17):137-9,
4040:
4036:
4031:
4023:
4014:
3994:
3990:
3981:
3973:
3969:
3960:
3952:
3948:
3938:
3934:
3926:
3922:
3918:
3914:
3906:
3902:
3896:
3887:
3881:
3867:
3863:
3852:
3848:
3841:
3837:
3828:
3816:
3804:
3800:
3795:
3770:
3766:
3756:
3747:
3736:. Retrieved
3732:the original
3722:
3689:
3685:
3675:
3656:
3637:
3629:
3619:
3600:
3596:March, Jerry
3589:
3571:
3562:
3548:
3521:, retrieved
3499:
3489:
3448:
3444:
3437:
3418:
3391:
3385:
3372:
3331:
3295:
3289:
3272:
3237:
3233:
3223:
3182:
3178:
3168:
3132:
3103:. Retrieved
3099:
3090:
3079:. Retrieved
3074:
3065:
3052:
3019:
3013:
2965:
2939:
2934:
2897:
2889:
2880:
2875:lists it in
2870:
2845:WAC Corporal
2838:
2809:penicillin G
2792:
2789:World War II
2766:
2740:
2703:magic bullet
2701:
2697:chemotherapy
2695:
2692:Paul Ehrlich
2680:side effects
2665:
2640:Aniline and
2633:
2587:
2577:
2573:
2565:
2562:nitrobenzene
2556:). In 1842,
2551:
2547:
2535:
2531:
2515:
2501:
2492:
2445:
2418:
2402:
2396:blue in the
2383:
2368:
2333:
2269:nitrous acid
2266:
2193:Boiled with
2192:
2178:
2174:
2170:
2169:
2119:
2115:
2108:
2095:
2094:
2088:
2048:
2030:
2018:
1979:
1962:
1911:formaldehyde
1908:
1901:
1874:
1831:
1821:Polyanilines
1811:polyanilines
1783:nitrobenzene
1755:Chromic acid
1751:arsenic acid
1744:
1724:
1680:
1652:
1641:
1622:
1605:hydrogenated
1602:
1586:
1582:
1558:
1511:
1481:
1475:
1459:
1453:
1438:
1426:polyurethane
1388:phenyl group
1361:
1357:
1349:
1348:
1288:Nitrobenzene
1202:
1129:
1107:Autoignition
1042:
858:
805:
795:Main hazards
784:
763:
714:
672:
621:1.0297 g/mL
413:RTECS number
126:Identifiers
117:Aminobenzene
113:Other names
18:Aniline salt
4134:20 November
4039:, 1880 May;
3855:(1): 84–90.
2904:tumorigenic
2853:nitric acid
2835:Rocket fuel
2785:sulfa drugs
2674:emerged as
2668:acetanilide
2600:discovered
2596:'s student
2594:von Hofmann
2574:phenylamine
2568:. In 1843,
2538:. In 1840,
2518:. In 1834,
2464:paracetamol
2398:Nissl stain
2091:-Alkylation
2082:acetanilide
2071:−C(=O)−NH−C
1881:precipitate
1791:oxalic acid
1683:derivatives
1589:methylamine
1561:amine group
1467:nucleophile
1403:amino group
1130:Lethal dose
1109:temperature
1096:Flash point
853:Signal word
789:(OHS/OSH):
738:(3.71
608:Appearance
564:Properties
555:c1ccc(cc1)N
314:100.000.491
236:CHEBI:17296
115:Phenylamine
106:Benzenamine
4382:Categories
4302:References
4064:():931-2,
3955:: 283–287.
3738:2007-12-21
3523:2022-02-01
3424:US3136818A
3105:2022-02-15
3081:2016-06-16
2908:DNA damage
2857:hypergolic
2817:René Dubos
2813:Gramicidin
2805:antibiotic
2781:Paul Gelmo
2736:penicillin
2672:phenacetin
2636:(English:
2516:Crystallin
2487:indigo dye
2476:blue jeans
2452:herbicides
2246:−N=C(−NH−C
1889:protection
1807:persulfate
1787:azobenzene
1761:, whereas
1747:azobenzene
1737:Sample of
1687:toluidines
1667:distillate
1599:Production
1354:Portuguese
1352:(from
817:Pictograms
756:combustion
596:Molar mass
445:576R1193YL
438:SIR7XX2F1K
267:ChemSpider
166:3D model (
133:CAS Number
3941:(1): 153.
3728:"Aniline"
3706:2092-7673
3358:cite book
3350:957525299
3264:2073-8994
3207:1463-9084
3071:"Aniline"
3049:"Aniline"
2914:in their
2861:hydrazine
2777:colorfast
2765:degraded
2755:prontosil
2741:In 1932,
2724:salvarsan
2716:arsenical
2676:analgesic
2657:Nigrosene
2606:synthetic
2371:phenazine
2328:known as
2234:guanidine
2203:S=C(−NH−C
2039:Acylation
2033:solvation
1994:anilinium
1990:aliphatic
1775:chloranil
1763:chlorates
1729:Oxidation
1721:Reactions
1691:xylidines
1663:toluidine
1659:safranine
1609:catalysts
1593:formamide
1571:with the
1569:lone pair
1565:sp and sp
1522:π-bonding
1488:Structure
1471:aliphatic
1449:diazonium
1445:oxidation
1368:with the
1027:P403+P233
1011:P333+P313
979:P308+P313
971:P304+P340
967:P302+P352
963:P301+P310
808:labelling
730:Viscosity
550:Nc1ccccc1
461:UN number
420:BW6650000
335:200-539-3
327:EC Number
256:ChEMBL538
119:Benzamine
4388:Anilines
4292:18793663
4215:21941546
4199:: 1–23.
4105:pp 202–3
4088:pp 150–1
3885:synonym
3714:94372490
3598:(2007),
3570:(1992),
3473:23695637
3410:71790138
3234:Symmetry
3215:26852720
3160:11469727
3059:(NIOSH).
3007:(NIOSH).
2877:Group 2A
2761:to be a
2720:syphilis
2700:for his
2684:caffeine
2646:azo dyes
2618:induline
2614:safranin
2602:mauveine
2566:benzidam
2560:reduced
2524:coal tar
2485:Cake of
2423:to give
2421:phosgene
2390:furfural
2343:aromatic
2335:coupling
2281:hydroxyl
2271:to form
2199:thiourea
2100:methanol
2063:anilides
2057:to give
2053:such as
1976:Basicity
1965:4,4'-MDI
1769:), give
1767:vanadium
1673:fusion.
1671:fuchsine
1503:at 252 K
1478:coal tar
1473:amines.
1256:Related
1245:100 ppm
1124:1.3–11%
1043:NFPA 704
779:Hazards
724:1.58364
700:(χ)
287:DrugBank
150:142-04-1
49:Aniline
43:annulene
4326:Aniline
4319::
4283:2614128
3821:308–332
3813:513–524
3775:Bibcode
3481:3273484
3453:Bibcode
3242:Bibcode
3187:Bibcode
3001:"#0033"
2841:Aerobee
2825:topical
2768:in vivo
2763:prodrug
2708:Béchamp
2610:fuchsin
2590:quinine
2578:aniline
2548:aniline
2498:History
2468:Tylenol
2373:in the
2340:primary
2305:halogen
2299:group (
2289:cyanide
2045:Anilide
1842:enamine
1834:phenols
1759:quinone
1707:toluene
1434:ignites
1370:formula
1350:Aniline
1331:what is
1329: (
669:Acidity
617:Density
590:
448: (
400: (
377:PubChem
296:DB06728
221:605631
153: (
143:62-53-3
94:Aniline
73:Aniline
39:alanine
4313:
4290:
4280:
4213:
3888:I anil
3815:; and
3712:
3704:
3663:
3608:
3578:
3514:
3479:
3471:
3430:
3408:
3398:
3348:
3338:
3310:
3262:
3213:
3205:
3158:
3148:
3026:
2958:
2900:spleen
2807:drug,
2712:atoxyl
2616:, and
2536:cyanol
2532:kyanol
2512:indigo
2472:indigo
2448:rubber
2322:phenol
2307:) via
2297:halide
2295:), or
2230:−N=C=S
2145:OH → C
2141:+ 2 CH
2106:gives
2059:amides
1934:O → CH
1797:gives
1644:phenol
1326:verify
1323:
859:Danger
601:93.129
543:SMILES
365:C00292
247:ChEMBL
204:B00082
196:3DMet
84:Names
4066:p 932
4045:p 138
3809:65–77
3710:S2CID
3477:S2CID
2927:Notes
2771:into
2743:Bayer
2638:Baden
2355:water
1832:Like
1713:into
1432:. It
1356:
1203:NIOSH
740:mPa·s
734:3.71
508:InChI
465:1547
350:2796
227:ChEBI
168:JSmol
41:, or
4393:Dyes
4288:PMID
4211:PMID
4197:2011
4136:2020
4123:Time
3702:ISSN
3661:ISBN
3606:ISBN
3576:ISBN
3512:ISBN
3469:PMID
3406:OCLC
3396:ISBN
3364:link
3346:OCLC
3336:ISBN
3308:ISBN
3260:ISSN
3211:PMID
3203:ISSN
3156:OCLC
3146:ISBN
3024:ISBN
2956:ISBN
2873:IARC
2843:and
2670:and
2642:Soda
2630:BASF
2458:and
2415:Uses
2357:and
2320:and
2314:NaNO
2161:+ 2H
2153:N(CH
2113:and
1982:base
1930:+ CH
1573:aryl
1559:The
1534:)−NH
1532:aryl
1456:base
1430:fish
1362:-ine
1358:anil
1239:IDLH
1232:Ca
1035:P501
1031:P405
1023:P391
1019:P363
1015:P361
1007:P330
1003:P322
999:P321
995:P314
991:P312
987:P311
983:P310
959:P281
955:P280
951:P273
947:P272
943:P271
939:P270
935:P264
931:P261
927:P260
923:P202
919:P201
905:H400
901:H372
897:H351
893:H341
889:H331
885:H318
881:H317
877:H311
873:H301
429:UNII
397:8870
390:6115
356:KEGG
276:5889
4328:",
4278:PMC
4270:doi
4266:233
4201:doi
4152:SSM
3783:doi
3694:doi
3504:doi
3461:doi
3300:doi
3278:doi
3250:doi
3195:doi
3138:doi
2974:-NH
2948:doi
2916:DNA
2819:at
2811:. (
2710:'s
2576:or
2534:or
2510:of
2506:by
2394:RNA
2351:HCl
2326:dye
2293:−CN
2287:),
2285:−OH
2259:).
2201:) (
2080:is
2016:).
2006:−NH
1954:+ H
1918:2 C
1883:of
1528:of
1407:−NH
1226:REL
1213:PEL
806:GHS
767:298
477:EPA
450:HCl
402:HCl
380:CID
155:HCl
4384::
4352:,
4286:.
4276:.
4264:.
4260:.
4248:^
4209:.
4195:.
4191:.
4120:.
4073:^
4062:77
4022:.
4009:.)
3995:42
3974:47
3972:,
3953:44
3951:,
3939:27
3937:,
3927:10
3925:,
3919:27
3917:,
3913:,
3907:10
3905:,
3868:20
3866:,
3862:,
3853:36
3851:,
3840:,
3819::
3817:32
3807::
3805:31
3803:,
3781:.
3769:.
3708:.
3700:.
3690:16
3688:.
3684:.
3647:^
3635:;
3628:.
3531:^
3510:,
3498:,
3475:.
3467:.
3459:.
3447:.
3404:.
3360:}}
3356:{{
3344:.
3322:^
3306:.
3258:.
3248:.
3236:.
3232:.
3209:.
3201:.
3193:.
3183:18
3181:.
3177:.
3154:.
3144:.
3114:^
3098:.
3073:.
3055:.
3051:.
3038:^
3003:.
2985:^
2964:.
2954:.
2887:.
2863:.
2738:.
2722:–
2690:,
2652:.
2612:,
2592:,
2580:.
2478:.
2407:.
2400:.
2381:.
2361:.
2301:−X
2137:NH
2124::
2067:CH
1984:.
1946:NH
1938:(C
1926:NH
1872:.
1866:SO
1858:NC
1852:,
1777:.
1701:,
1697:,
1693:,
1689:,
1650:.
1551:.
1530:C(
1484:.
1463:aH
1458:(p
1392:−C
1381:NH
1184:Lo
1182:LC
1166:50
1164:LC
1140:Lo
1138:LD
1033:,
1029:,
1025:,
1021:,
1017:,
1013:,
1009:,
1005:,
1001:,
997:,
993:,
989:,
985:,
981:,
977:,
973:,
969:,
965:,
961:,
957:,
953:,
949:,
945:,
941:,
937:,
933:,
929:,
925:,
921:,
903:,
899:,
895:,
891:,
887:,
883:,
879:,
875:,
810::
759:(Δ
736:cP
688:O)
678:)
671:(p
585:NH
4294:.
4272::
4217:.
4203::
4138:.
4107:.
4090:.
4068:.
4047:.
4041:2
4003:3
4001:O
3999:2
3874:.
3842:7
3789:.
3785::
3777::
3771:8
3741:.
3716:.
3696::
3669:.
3642:.
3556:.
3506::
3483:.
3463::
3455::
3449:5
3412:.
3380:.
3366:)
3352:.
3316:.
3302::
3284:.
3280::
3266:.
3252::
3244::
3238:2
3217:.
3197::
3189::
3162:.
3140::
3108:.
3084:.
3032:.
2976:2
2972:5
2970:H
2968:6
2950::
2879:(
2316:2
2291:(
2283:(
2256:2
2254:)
2252:5
2250:H
2248:6
2244:5
2242:H
2240:6
2238:C
2236:(
2228:5
2226:H
2224:6
2222:C
2220:(
2213:2
2211:)
2209:5
2207:H
2205:6
2179:N
2177:,
2175:N
2171:N
2165:O
2163:2
2159:2
2157:)
2155:3
2151:5
2149:H
2147:6
2143:3
2139:2
2135:5
2133:H
2131:6
2129:C
2120:N
2118:,
2116:N
2109:N
2096:N
2089:N
2077:5
2075:H
2073:6
2069:3
2012:3
2009:+
2004:5
2002:H
2000:6
1998:C
1958:O
1956:2
1952:2
1950:)
1948:2
1944:4
1942:H
1940:6
1936:2
1932:2
1928:2
1924:5
1922:H
1920:6
1870:H
1868:3
1864:4
1862:H
1860:6
1856:2
1854:H
1536:2
1514:Å
1460:K
1409:2
1405:(
1398:5
1396:H
1394:6
1390:(
1383:2
1379:5
1377:H
1375:6
1373:C
1321:N
1190:)
1186:(
1172:)
1168:(
1146:)
1142:(
1084:0
1077:2
1070:3
769:)
764:H
761:c
720:)
718:D
715:n
713:(
686:2
676:a
673:K
587:2
583:5
581:H
579:6
577:C
479:)
475:(
452:)
404:)
170:)
157:)
45:.
34:.
20:)
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