1067:
75:
437:
282:
2602:
810:
49:
59:
805:
815:
795:
800:
2352:
1062:
2510:
1065:
1275:
1066:
2720:, with a theoretical decomposition energy of about 5 kJ/g, and aqueous solutions above 80% can be easily detonated by detonator or strong heating under confinement. At least two factories dealing in hydroxylamine have been destroyed since 1999 with loss of life. It is known, however, that ferrous and ferric
2638:
Hydroxylamine can also be used to better characterize the nature of a post-translational modification onto proteins. For example, poly(ADP-Ribose) chains are sensitive to hydroxylamine when attached to glutamic or aspartic acids but not sensitive when attached to serines. Similarly, Ubiquitin
2203:
This reaction is useful in the purification of ketones and aldehydes: if hydroxylamine is added to an aldehyde or ketone in solution, an oxime forms, which generally precipitates from solution; heating the precipitate with an inorganic acid then restores the original aldehyde or ketone.
2570:
are seemingly able to modify other regions of the DNA & lead to other types of mutations. This may be due to the ability of hydroxylamine to undergo uncontrolled free radical chemistry in the presence of trace metals and oxygen, in fact in the absence of its free radical affects
1090:
2575:
noted hydroxylamine was unable to induce reversion mutations of its C:G to T:A transition effect & even considered hydroxylamine to be the most specific mutagen known. Practically, it has been largely surpassed by more potent mutagens such as
2634:
Some non-chemical uses include removal of hair from animal hides and photographic developing solutions. In the semiconductor industry, hydroxylamine is often a component in the "resist stripper", which removes photoresist after lithography.
823:
775:
3178:
Zhang, Xiaoping; Su, Rui; Li, Jingling; Huang, Liping; Yang, Wenwen; Chingin, Konstantin; Balabin, Roman; Wang, Jingjing; Zhang, Xinglei; Zhu, Weifeng; Huang, Keke; Feng, Shouhua; Chen, Huanwen (2024).
74:
3355:
Kirby, AJ; Davies, JE; Fox, DJ; Hodgson, DR; Goeta, AE; Lima, MF; Priebe, JP; Santaballa, JA; Nome, F (28 February 2010). "Ammonia oxide makes up some 20% of an aqueous solution of hydroxylamine".
2417:
Similarly to amines, one can distinguish hydroxylamines by their degree of substitution: primary, secondary and tertiary. When stored exposed to air for weeks, secondary hydroxylamines degrade to
3836:
Arciero, David M.; Hooper, Alan B.; Cai, Mengli; Timkovich, Russell (1993-09-01). "Evidence for the structure of the active site heme P460 in hydroxylamine oxidoreductase of
Nitrosomonas".
957:
3534:
Busby, Stephen; Irani, Meher; de
Crombrugghe, BenoΓt (1982). "Isolation of mutant promoters in the Escherichia coli galactose operon using local mutagenesis on cloned DNA fragments".
2270:
can easily explode aqueous solutions concentrated above 80% by weight, and even 50% solution might prove detonable if tested in bulk. In air, the combustion is rapid and complete:
1288:
3094:
2822:
4020:
Cisneros, L. O.; Rogers, W. J.; Mannan, M. S.; Li, X.; Koseki, H. (2003). "Effect of Iron Ion in the
Thermal Decomposition of 50 mass% Hydroxylamine/Water Solutions".
3987:
1398:
1068:
2566:
to hydroxyaminocytidine, which is misread as thymidine, thereby inducing C:G to T:A transition mutations. But high concentrations or over-reaction of hydroxylamine
48:
1076:
2551:
Hydroxylamine and its salts are commonly used as reducing agents in myriad organic and inorganic reactions. They can also act as antioxidants for fatty acids.
4135:
486:
953:
4098:
3963:
3586:
3439:
3262:
2879:
2841:
2806:
2639:
molecules bound to serines or threonines residues are sensitive to hydroxylamine, but those bound to lysine (isopeptide bond) are resistant.
744:
4003:
4103:
2588:, but being a very small mutagenic compound with high specificity, it found some specialized uses such as mutation of DNA packed within
3488:
Waugh, Robbie; Leader, David J.; McCallum, Nicola; Caldwell, David (2006). "Harvesting the potential of induced biological diversity".
1442:) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on
1083:
3323:
58:
3333:
3073:
2854:
451:
4128:
4849:
945:
3111:
3159:
3771:"The E3 ligase HOIL-1 catalyses ester bond formation between ubiquitin and components of the Myddosome in mammalian cells"
2230:
1546:
1250:
937:
1295:
901:
891:
394:
993:
814:
809:
4121:
2585:
2068:
929:
415:
2918:"Structural conservation of the B subunit in the ammonia monooxygenase/particulate methane monooxygenase superfamily"
1029:
804:
4864:
4834:
2790:
2673:
629:
603:
4839:
2400:
2174:
1846:
1378:
1226:
1178:
879:
289:
4859:
2368:
1653:
1188:
1183:
1113:
339:
3704:
Langelier, Marie-France; Billur, Ramya; Sverzhinsky, Aleksandr; Black, Ben E.; Pascal, John M. (2021-11-18).
989:
794:
4844:
2705:
969:
675:
345:
2605:
This route also involves the
Beckmann Rearrangement, like the conversion from cyclohexanone to caprolactam.
961:
799:
277:
4630:
4062:
3706:"HPF1 dynamically controls the PARP1/2 balance between initiating and elongating ADP-ribose modifications"
2577:
2532:
2514:
2468:
is the most common method to synthesize hydroxylamines. Care must be taken to prevent over-oxidation to a
2296:
Absent air, pure hydroxylamine requires stronger heating and the detonation does not complete combustion:
1910:
720:
239:
3881:"Nitrosomonas europaea cytochrome P460 is a direct link between nitrification and nitrous oxide emission"
4854:
4706:
4609:
4225:
3189:
2677:
2659:
2655:
2076:
837:
787:
653:
590:
87:
3282:
2601:
4641:
4622:
4420:
4408:
3892:
3782:
3717:
3623:
1402:
1238:
965:
97:
4649:
4614:
4365:
2787:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2524:
2226:
1419:(zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating.
921:
432:
147:
4727:
4751:
4743:
4657:
4520:
4357:
4083:, Coll. Vol. 6, p. 943; Vol. 58, p. 32. (preparation of hydroxylamine-O-sulfonic acid).
3981:
3134:
3056:
Walker, John E.; Howell, David M. (1967). "Dichlorobis(hydroxylamine)zinc(II) (Crismer's Salt)".
2816:
1315:
913:
671:
665:
4000:
3769:
Kelsall, Ian R.; Zhang, Jiazhen; Knebel, Axel; Arthur, J. Simon C.; Cohen, Philip (2019-07-02).
1147:
408 mg/kg (oral, mouse); 59β70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat)
973:
909:
199:
1009:
925:
4533:
3969:
3959:
3928:
3910:
3861:
3853:
3818:
3800:
3751:
3733:
3678:
3659:
3641:
3592:
3582:
3559:
3551:
3513:
3505:
3435:
3372:
3329:
3302:
3258:
3248:
3216:
3107:
3069:
3035:
3014:
2973:
2955:
2937:
2875:
2850:
2802:
2740:
2259:
2060:
1965:
1918:
1390:
1221:
1152:
941:
4079:
M. W. Rathke A. A. Millard "Boranes in
Functionalization of Olefins to Amines: 3-Pinanamine"
4802:
4581:
4476:
4401:
4273:
4029:
3951:
3918:
3900:
3845:
3808:
3790:
3741:
3725:
3649:
3631:
3543:
3497:
3468:
3399:
3364:
3294:
3206:
3198:
3099:
3061:
2945:
2929:
2794:
2744:
2733:
2700:
peptide bonds in peptides and proteins. It also bonds to and permanently disables (poisons)
2465:
2208:
2196:
2103:
2087:
1765:
1553:
1465:
1428:
1345:
1319:
579:
509:
4108:
1017:
977:
403:
4764:
4566:
4464:
4093:
4074:
4007:
2392:
2346:
2186:
2072:
1870:
981:
949:
905:
308:
157:
1158:
259:
3896:
3786:
3721:
3627:
3211:
3180:
3128:
1001:
436:
281:
219:
4718:
4673:
4665:
4345:
4332:
4310:
4209:
3923:
3880:
3813:
3770:
3746:
3705:
3254:
2950:
2917:
2686:
2351:
1761:
1575:
1382:
1266:
897:
3654:
3611:
3298:
2509:
4828:
4681:
4544:
4528:
4499:
3955:
3946:
Bornstein, Paul; Balian, Gary (1977). "Cleavage at AsnGly bonds with hydroxylamine".
3547:
2682:
2589:
2495:
2476:
2411:
2396:
2323:
2099:
1922:
1902:
1481:
1462:
1394:
1366:
701:
568:
558:
270:
181:
4046:
2732:
solutions. Hydroxylamine and its derivatives are more safely handled in the form of
1041:
4790:
4735:
4689:
4553:
4377:
4353:
4315:
4175:
2572:
2064:
1961:
1898:
1783:, a side-product insoluble in liquid ammonia, is removed by filtration; the liquid
1501:
1485:
1443:
917:
863:
3501:
2747:. It may be absorbed through the skin, is harmful if swallowed, and is a possible
2903:
2nd
Edition. Reed Educational and Professional Publishing Ltd. pp. 431β432. 1997.
933:
4697:
4483:
4432:
4396:
3950:. Methods in Enzymology. Vol. 47(Enzyme Struct., Part E). pp. 132β45.
3612:"Localized Mutagenesis of Any Specific Small Region of the Bacterial Chromosome"
2916:
Lawton, Thomas J.; Ham, Jungwha; Sun, Tianlin; Rosenzweig, Amy C. (2014-09-01).
2798:
2701:
2612:
2555:
2536:
2491:
2327:
1914:
1338:
1140:
1102:
871:
367:
3729:
3418:
March's advanced organic chemistry : reactions, mechanisms, and structure.
3202:
2543:). The latter can then undergo a ring-opening polymerization to yield Nylon 6.
997:
4305:
3065:
2765:
2693:
2665:
2616:
2559:
2485:
1649:
527:
250:
31:
17:
3914:
3857:
3804:
3737:
3645:
3596:
3555:
3509:
3306:
3103:
2941:
4778:
4508:
4451:
4291:
4197:
3905:
3795:
3636:
3579:
Chemical
Mutagens : Principles and Methods for Their Detection Volume 1
2846:
2717:
2562:
amine-hydroxylating agent. In is thought to mainly act via hydroxylation of
2267:
1969:
1874:
1561:
1216:
1033:
1025:
855:
3932:
3822:
3755:
3517:
3376:
3220:
2959:
875:
52:
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added
3879:
Caranto, Jonathan D.; Vilbert, Avery C.; Lancaster, Kyle M. (2016-12-20).
3865:
3663:
3563:
883:
847:
4786:
4472:
4283:
4167:
4144:
3973:
3473:
3456:
2628:
2620:
2563:
2554:
High concentrations of hydroxylamine are used by biologists to introduce
2150:
2111:
2083:
1624:
1505:
1492:
1489:
1326:
1323:
1089:
1082:
1075:
1048:
867:
3849:
3403:
4808:
4796:
4772:
4439:
4384:
4327:
4300:
4278:
4268:
4183:
4159:
3235:
The
Systematic Identification of Organic Compounds: A Laboratory Manual
3092:
Ritz, Josef; Fuchs, Hugo; Perryman, Howard G. (2000). "Hydroxylamine".
2933:
2748:
2697:
2528:
2469:
2432:
2418:
1906:
1817:
1793:
1784:
1613:
1550:
1432:
1357:
1349:
1341:
1206:
548:
354:
290:
4033:
859:
3368:
2911:
2909:
2669:
2624:
2371:
in place of the hydroxyl or amine hydrogen are (respectively) called
2212:
2166:
2154:
2107:
1332:
684:
230:
1265:
Except where otherwise noted, data are given for materials in their
851:
4113:
328:
4260:
4255:
4247:
4217:
2760:
2508:
2480:
2436:
2350:
2158:
1592:
1557:
1397:. It was first prepared in pure form in 1891 by the Dutch chemist
1353:
1211:
843:
378:
210:
180:
170:
1021:
4814:
2721:
2708:
of photosynthesis on account of its similar structure to water.
1787:
is evaporated to give the desired product. The net reaction is:
1401:
and by the French chemist LΓ©on
Maurice Crismer (1858-1944). The
1037:
319:
4117:
4109:
Deadly detonation of hydroxylamine at Concept Sciences facility
2523:
Approximately 95% of hydroxylamine is used in the synthesis of
1005:
4001:
Japan Science and Technology Agency Failure Knowledge Database
2581:
1386:
1013:
3233:
Ralph Lloyd Shriner, Reynold C. Fuson, and Daniel Y. Curtin,
3281:
Iwata, Yusaku; Koseki, Hiroshi; Hosoya, Fumio (2003-01-01).
3161:
Process of preparing hydroxylamine hydrochloride (US2242477)
2692:
Hydroxylamine can also be used to highly selectively cleave
985:
573:
58 Β°C (136 Β°F; 331 K) /22 mm Hg (decomposes)
420:
57:
47:
3185:
fixation by water radical cations under ambient conditions"
2383:‑hydroxylamines are more common. Examples are
3146:
manufacture of chemicals by electrolysis hydroxylamine 32.
4067:
Walters, Michael A. and Andrew B. Hoem. "Hydroxylamine."
3430:
Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012).
2513:
Conversion of cyclohexanone to caprolactam involving the
1344:. Hydroxylamine is almost always provided and used as an
1060:
3283:"Study on decomposition of hydroxylamine/water solution"
1960:
Hydroxylamine can also be produced by the reduction of
1283:
3434:(2nd ed.). Oxford University Press. p. 958.
3133:(1st ed.). New York: D. Van Nostrand Co. p.
3457:"Ring-Opening PolymerizationβAn Introductory Review"
3287:
Journal of Loss Prevention in the Process Industries
2531:. The treatment of this oxime with acid induces the
4763:
4602:
4344:
4240:
4152:
4094:
Calorimetric studies of hydroxylamine decomposition
3390:Hamer, Jan; Macaluso, Anthony (1964) . "Nitrones".
1841:A base then frees the hydroxylamine from the salt:
3325:Bretherick's Handbook of Reactive Chemical Hazards
4069:e-Encyclopedia of Reagents for Organic Synthesis.
2922:Proteins: Structure, Function, and Bioinformatics
2834:
2832:
2704:. It is used as an irreversible inhibitor of the
2662:(HAO) further oxidizes hydroxylamine to nitrite.
198:
30:"Aminol" redirects here. Not to be confused with
366:
3885:Proceedings of the National Academy of Sciences
3775:Proceedings of the National Academy of Sciences
3616:Proceedings of the National Academy of Sciences
2613:alternative industrial synthesis of paracetamol
1348:. It is consumed almost exclusively to produce
1064:
156:
3455:Nuyken, Oskar; Pask, Stephen (25 April 2013).
3095:Ullmann's Encyclopedia of Industrial Chemistry
2647:In biological nitrification, the oxidation of
2391:‑butylhydroxylamine or the
4129:
3529:
3527:
3237:, 5th ed. (New York: Wiley, 1964), chapter 6.
3036:"PrΓ©paration de l'hydroxylamine cristallisΓ©e"
2821:: CS1 maint: DOI inactive as of April 2024 (
8:
3986:: CS1 maint: multiple names: authors list (
3130:The Manufacture of Chemicals by Electrolysis
3038:(Preparation of crystalized hydroxylamine),
2872:Chemical Risk Analysis: A Practical Handbook
2427:‑organylhydroxylamines,
4136:
4122:
4114:
3679:"Hydroxylamine Mutagenesis of plasmid DNA"
3158:Osswald, Philipp; Geisler, Walter (1941).
3087:
3085:
3019:Recueil des travaux chimiques des Pays-Bas
2724:salts accelerate the decomposition of 50%
2082:A direct production of hydroxylamine from
435:
280:
258:
36:
3922:
3904:
3812:
3794:
3745:
3653:
3635:
3472:
3210:
2949:
2379:‑hydroxylamines. In general
1365:to hydroxylamine is a step in biological
402:
3040:Bulletin de la SociΓ©tΓ© chimique de Paris
2727:
2650:
2600:
2592:capsids, & mutation of purified DNA
2451:
2441:
2332:
2314:
2310:
2306:
2302:
2288:
2284:
2280:
2276:
2266:When heated, hydroxylamine explodes. A
2255:
2251:
2247:
2243:
2220:
2190:
2182:
2176:
2168:
2144:
2133:
2124:
2120:
2043:
2039:
2004:
2000:
1978:
1952:
1948:
1944:
1940:
1929:
1925:
1884:
1880:
1876:
1866:
1862:
1858:
1854:
1848:
1833:
1829:
1813:
1809:
1805:
1779:
1775:
1771:
1755:
1736:
1732:
1728:
1724:
1689:
1685:
1666:
1662:
1658:
1641:
1626:
1620:
1615:
1609:
1605:
1601:
1578:
1540:
1524:
1520:
1516:
1512:
1507:
1475:
1471:
1456:
1437:
1415:
1411:
1407:
1360:
1329:
659:Tricoordinated at N, dicoordinated at O
619:
517:
3610:Hong, J.-S.; Ames, B. N. (1971-12-01).
3581:. Boston, MA: Springer US. p. 41.
2895:
2893:
2891:
2777:
1337:. The compound is in a form of a white
491:
456:
431:
344:
3979:
2874:. ButterworthβHeinemann. p. 362.
2814:
1583:at 0 Β°C to yield a hydroxylamido-
1121:265 Β°C (509 Β°F; 538 K)
1107:129 Β°C (264 Β°F; 402 K)
271:
3318:
3316:
3276:
3274:
2842:CRC Handbook of Chemistry and Physics
1468:, hydroxylammonium hydrogen sulfate (
463:Key: AVXURJPOCDRRFD-UHFFFAOYSA-N
238:
218:
62:Ball-and-stick model of hydroxylamine
7:
2654:to hydroxylamine is mediated by the
2337:contributes to the high reactivity.
1377:Hydroxylamine was first prepared as
563:33 Β°C (91 Β°F; 306 K)
553:1.21 g cm (at 20 Β°C)
3685:. University of Southern California
3247:Wiberg, Egon; Wiberg, Nils (2001).
2408:‑Dimethylhydroxylamine
1760:can be collected by treatment with
1431:(salts containing hydroxylammonium
473:Key: AVXURJPOCDRRFD-UHFFFAOYAD
357:
327:
4075:Schupf Computational Chemistry Lab
1495:in the presence of sulfuric acid.
25:
2845:(87th ed.). Boca Raton, FL:
2712:Safety and environmental concerns
2106:, which can attach to either the
3416:Smith, Michael and Jerry March.
2870:Martel, B.; Cassidy, K. (2004).
1273:
813:
808:
803:
798:
793:
102:Hydroxylamine (only preselected)
73:
3420:New York. Wiley. p. 1554. 2001.
2681:, can convert hydroxylamine to
1269:(at 25 Β°C , 100 kPa).
3577:Hollaender, Alexander (1971).
2984: : 551-553. From p. 551:
2791:The Royal Society of Chemistry
1901:discovered that hydroxylamine
1381:in 1865 by the German chemist
1171:Related hydroxylammonium salts
1:
3502:10.1016/j.tplants.2005.12.007
3299:10.1016/S0950-4230(02)00072-4
3060:. Vol. 9. pp. 2β3.
543:Vivid white, opaque crystals
3956:10.1016/0076-6879(77)47016-2
3548:10.1016/0022-2836(82)90060-2
3536:Journal of Molecular Biology
3013:C. A. Lobry de Bruyn (1891)
2839:Lide, David R., ed. (2006).
2660:Hydroxylamine oxidoreductase
3542:(2). Elsevier BV: 197β209.
3127:James Hale, Arthur (1919).
3015:"Sur l'hydroxylamine libre"
2986:"Ich schlage vor, dieselbe
2799:10.1039/9781849733069-FP001
2623:involves the conversion of
2069:hydroxylamine hydrochloride
1129:or concentration (LD, LC):
43:
4881:
4099:Chemical company BASF info
3730:10.1038/s41467-021-27043-8
3203:10.1038/s41467-024-45832-9
3181:"Efficient catalyst-free N
2901:Chemistry of the Elements.
2674:ammonia-oxidizing bacteria
2367:Hydroxylamine derivatives
2344:
2098:Hydroxylamine reacts with
1461:is mainly produced as its
460:InChI=1S/H3NO/c1-2/h2H,1H2
29:
3496:(2). Elsevier BV: 71β79.
3066:10.1002/9780470132401.ch2
3017:(On free hydroxylamine),
2974:"Ueber das Hydroxylamine"
2739:It is an irritant to the
2488:a precursor hydroxylamine
2472:. Other methods include:
2435:group, can be reduced to
1909:salts can be produced by
1379:hydroxylammonium chloride
1263:
1179:Hydroxylammonium chloride
1164:
1125:
774:
769:
694:
646:
502:
482:
470:InChI=1/H3NO/c1-2/h2H,1H2
447:
140:
108:
96:
86:
81:
72:
42:
3104:10.1002/14356007.a13_527
2899:Greenwood and Earnshaw.
2743:, skin, eyes, and other
2716:Hydroxylamine can be an
2450:RβNHβOH (Zn, HCl) β RβNH
1654:hydroxylammonium sulfate
1385:(1838-1906); he reacted
1189:Hydroxylammonium sulfate
1184:Hydroxylammonium nitrate
892:Precautionary statements
3948:Enzyme Structure Part E
3906:10.1073/pnas.1611051113
3796:10.1073/pnas.1905873116
3637:10.1073/pnas.68.12.3158
3490:Trends in Plant Science
3357:Chemical Communications
3098:. Weinheim: Wiley-VCH.
2801:(inactive 2024-04-26).
2706:oxygen-evolving complex
2702:heme-containing enzymes
4850:Photographic chemicals
2996:(I propose to call it
2978:Zeitschrift fΓΌr Chemie
2606:
2533:Beckmann rearrangement
2518:
2515:Beckmann rearrangement
2364:
1911:electrolytic reduction
1383:Wilhelm Clemens Lossen
1234:-Dimethylhydroxylamine
1071:
63:
53:
3710:Nature Communications
3190:Nature Communications
3167:. U.S. Patent Office.
2793:. 2014. p. 993.
2656:ammonia monooxygenase
2604:
2512:
2464:Amine oxidation with
2363:-hydroxylamine schema
2354:
2211:are also employed as
1427:Hydroxylamine or its
1246:-Diethylhydroxylamine
1070:
654:Coordination geometry
61:
51:
3474:10.3390/polym5020361
3257:. pp. 675β677.
2976:(On hydroxylamine),
2972:W. C. Lossen (1865)
2678:Nitrosomonas europea
2631:with hydroxylamine.
2086:is also possible in
1403:coordination complex
1053:(fire diamond)
98:Preferred IUPAC name
3897:2016PNAS..11314704C
3891:(51): 14704β14709.
3850:10.1021/bi00087a016
3787:2019PNAS..11613293K
3781:(27): 13293β13298.
3722:2021NatCo..12.6675L
3628:1971PNAS...68.3158H
3404:10.1021/cr60230a006
3250:Inorganic Chemistry
3058:Inorganic Syntheses
2558:by acting as a DNA
2525:cyclohexanone oxime
2227:chlorosulfonic acid
2077:the hydroxamic acid
1648:This anion is then
1393:in the presence of
580:Solubility in water
535: gΒ·mol
39:
4022:J. Chem. Eng. Data
4006:2007-12-20 at the
3034:L. Crismer (1891)
2934:10.1002/prot.24535
2607:
2519:
2410:is a precursor to
2365:
2084:molecular nitrogen
2063:disproportionates
2056:(100 Β°C, 1 h)
1316:inorganic compound
1296:Infobox references
1165:Related compounds
1072:
672:Trigonal pyramidal
64:
54:
37:
27:Inorganic compound
4865:Nitrogen oxoacids
4835:Functional groups
4822:
4821:
4081:Organic Syntheses
4034:10.1021/je030121p
3965:978-0-12-181947-7
3844:(36): 9370β9378.
3677:Forsberg, Susan.
3622:(12): 3158β3162.
3588:978-1-4615-8968-6
3441:978-0-19-927029-3
3432:Organic chemistry
3264:978-0-12-352651-9
2881:978-1-903996-65-2
2808:978-0-85404-182-4
2741:respiratory tract
2527:, a precursor to
2136:OH β RβNHβOH + HX
2104:alkylating agents
2061:Hydrochloric acid
1966:potassium nitrite
1537:Another route to
1450:From nitric oxide
1391:hydrochloric acid
1304:Chemical compound
1302:
1301:
1222:Hydrogen peroxide
1199:Related compounds
1153:Safety data sheet
838:Hazard statements
738:236.18 J/(KΒ·mol)
416:CompTox Dashboard
182:Interactive image
68:
67:
16:(Redirected from
4872:
4840:Inorganic amines
4812:
4800:
4776:
4765:Oxidation states
4594:
4593:
4562:
4561:
4496:
4495:
4460:
4459:
4448:
4447:
4393:
4392:
4138:
4131:
4124:
4115:
4050:
4044:
4038:
4037:
4028:(5): 1164β1169.
4017:
4011:
3998:
3992:
3991:
3985:
3977:
3943:
3937:
3936:
3926:
3908:
3876:
3870:
3869:
3833:
3827:
3826:
3816:
3798:
3766:
3760:
3759:
3749:
3701:
3695:
3694:
3692:
3690:
3674:
3668:
3667:
3657:
3639:
3607:
3601:
3600:
3574:
3568:
3567:
3531:
3522:
3521:
3485:
3479:
3478:
3476:
3452:
3446:
3445:
3427:
3421:
3414:
3408:
3407:
3392:Chemical Reviews
3387:
3381:
3380:
3369:10.1039/b923742a
3352:
3346:
3345:
3343:
3342:
3320:
3311:
3310:
3278:
3269:
3268:
3244:
3238:
3231:
3225:
3224:
3214:
3197:(1) 1535: 1535.
3175:
3169:
3168:
3166:
3155:
3149:
3148:
3143:
3141:
3124:
3118:
3117:
3089:
3080:
3079:
3053:
3047:
3046: : 793-795.
3032:
3026:
3025: : 100-112.
3011:
3005:
2970:
2964:
2963:
2953:
2928:(9): 2263β2267.
2913:
2904:
2897:
2886:
2885:
2867:
2861:
2860:
2836:
2827:
2826:
2820:
2812:
2785:"Front Matter".
2782:
2745:mucous membranes
2731:
2653:
2586:nitrosoguanidine
2466:benzoyl peroxide
2455:
2444:
2431:, where R is an
2430:
2341:Functional group
2336:
2318:
2292:
2262:
2224:
2209:dimethylglyoxime
2194:
2148:
2141:The reaction of
2137:
2128:
2055:
2054:
2053:
2050:
2037:
2036:
2033:
2025:
2024:
2023:
2020:
2015:
2014:
2011:
1998:
1997:
1994:
1989:
1988:
1985:
1956:
1932:
1889:
1837:
1826:
1825:
1822:
1802:
1801:
1798:
1782:
1766:Ammonium sulfate
1759:
1748:
1747:
1746:
1743:
1722:
1721:
1718:
1710:
1709:
1708:
1705:
1700:
1699:
1696:
1683:
1682:
1679:
1669:
1644:
1639:
1638:
1635:
1581:
1572:
1571:
1570:
1567:
1554:ammonium nitrite
1544:
1528:
1479:
1460:
1441:
1418:
1363:
1346:aqueous solution
1336:
1320:chemical formula
1286:
1280:
1277:
1276:
1092:
1085:
1078:
1063:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1015:
1011:
1007:
1003:
999:
995:
991:
987:
983:
979:
975:
971:
967:
963:
959:
955:
951:
947:
943:
939:
935:
931:
927:
923:
919:
915:
911:
907:
903:
899:
885:
881:
877:
873:
869:
865:
861:
857:
853:
849:
845:
817:
812:
807:
802:
797:
761:
734:
714:46.47 J/(KΒ·mol)
710:
695:Thermochemistry
623:
534:
521:
510:Chemical formula
440:
439:
424:
422:
406:
370:
359:
348:
331:
309:Gmelin Reference
292:
284:
273:
262:
242:
222:
202:
184:
160:
77:
44:
40:
21:
4880:
4879:
4875:
4874:
4873:
4871:
4870:
4869:
4860:Reducing agents
4825:
4824:
4823:
4818:
4806:
4794:
4770:
4759:
4755:
4747:
4739:
4731:
4722:
4714:
4710:
4701:
4693:
4685:
4677:
4669:
4661:
4653:
4645:
4635:
4626:
4618:
4598:
4592:
4589:
4588:
4587:
4585:
4578:
4574:
4570:
4560:
4557:
4556:
4555:
4548:
4541:
4537:
4524:
4516:
4512:
4503:
4494:
4491:
4490:
4489:
4487:
4480:
4468:
4458:
4455:
4454:
4453:
4446:
4443:
4442:
4441:
4436:
4428:
4424:
4416:
4412:
4405:
4391:
4388:
4387:
4386:
4381:
4373:
4369:
4361:
4340:
4336:
4323:
4319:
4295:
4287:
4264:
4251:
4236:
4230:
4221:
4213:
4205:
4201:
4192:
4179:
4171:
4163:
4148:
4142:
4090:
4059:
4057:Further reading
4054:
4053:
4045:
4041:
4019:
4018:
4014:
4008:Wayback Machine
3999:
3995:
3978:
3966:
3945:
3944:
3940:
3878:
3877:
3873:
3835:
3834:
3830:
3768:
3767:
3763:
3703:
3702:
3698:
3688:
3686:
3676:
3675:
3671:
3609:
3608:
3604:
3589:
3576:
3575:
3571:
3533:
3532:
3525:
3487:
3486:
3482:
3454:
3453:
3449:
3442:
3429:
3428:
3424:
3415:
3411:
3389:
3388:
3384:
3354:
3353:
3349:
3340:
3338:
3336:
3322:
3321:
3314:
3280:
3279:
3272:
3265:
3246:
3245:
3241:
3232:
3228:
3184:
3177:
3176:
3172:
3164:
3157:
3156:
3152:
3139:
3137:
3126:
3125:
3121:
3114:
3091:
3090:
3083:
3076:
3055:
3054:
3050:
3033:
3029:
3012:
3008:
2971:
2967:
2915:
2914:
2907:
2898:
2889:
2882:
2869:
2868:
2864:
2857:
2838:
2837:
2830:
2813:
2809:
2784:
2783:
2779:
2774:
2757:
2729:
2725:
2714:
2652:
2648:
2645:
2549:
2547:Laboratory uses
2505:
2494:pyrolysis (the
2462:
2453:
2449:
2443:
2439:
2428:
2393:glycosidic bond
2349:
2347:Hydroxamic acid
2343:
2334:
2330:
2316:
2312:
2308:
2304:
2300:
2290:
2286:
2282:
2278:
2274:
2257:
2253:
2249:
2245:
2241:
2222:
2218:
2207:Oximes such as
2192:
2184:
2178:
2170:
2165:
2146:
2142:
2135:
2131:
2126:
2122:
2118:
2096:
2073:carbon monoxide
2051:
2048:
2047:
2045:
2041:
2034:
2031:
2030:
2028:
2021:
2018:
2017:
2012:
2009:
2008:
2006:
2002:
1995:
1992:
1991:
1986:
1983:
1982:
1980:
1976:
1954:
1950:
1946:
1942:
1938:
1931:
1927:
1923:
1896:
1886:
1882:
1878:
1868:
1864:
1860:
1856:
1850:
1845:
1835:
1831:
1823:
1820:
1819:
1815:
1811:
1807:
1799:
1796:
1795:
1791:
1781:
1777:
1773:
1769:
1757:
1753:
1744:
1741:
1740:
1738:
1734:
1730:
1726:
1719:
1716:
1715:
1713:
1706:
1703:
1702:
1697:
1694:
1693:
1691:
1687:
1680:
1677:
1676:
1674:
1668:
1664:
1660:
1656:
1643:
1636:
1633:
1632:
1628:
1622:
1617:
1611:
1607:
1603:
1599:
1580:
1576:
1568:
1565:
1564:
1562:
1547:Raschig process
1542:
1538:
1535:
1533:Raschig process
1526:
1522:
1518:
1514:
1509:
1499:
1477:
1473:
1469:
1458:
1454:
1452:
1439:
1435:
1425:
1417:
1413:
1409:
1405:
1375:
1362:
1358:
1331:
1322:
1310:(also known as
1305:
1298:
1293:
1292:
1291: ?)
1282:
1278:
1274:
1270:
1259:
1200:
1193:
1172:
1144:
1138:
1118:
1115:
1097:
1096:
1095:
1094:
1087:
1080:
1073:
1069:
1061:
894:
840:
826:
790:
762:
759:
753:
749:
746:
745:Std enthalpy of
735:
732:
725:
722:
711:
704:
687:
668:
666:Molecular shape
656:
638:
621:
617:
612:
582:
532:
519:
515:
512:
498:
495:
490:
489:
478:
475:
474:
471:
465:
464:
461:
455:
454:
443:
425:
418:
409:
389:
373:
360:
334:
311:
302:
265:
245:
225:
205:
187:
174:
163:
150:
136:
135:
104:
103:
92:
35:
28:
23:
22:
15:
12:
11:
5:
4878:
4876:
4868:
4867:
4862:
4857:
4852:
4847:
4845:Hydroxylamines
4842:
4837:
4827:
4826:
4820:
4819:
4769:
4767:
4761:
4760:
4758:
4757:
4753:
4749:
4745:
4741:
4737:
4733:
4729:
4725:
4720:
4716:
4712:
4708:
4704:
4699:
4695:
4691:
4687:
4683:
4679:
4675:
4671:
4667:
4663:
4659:
4655:
4651:
4647:
4643:
4639:
4633:
4628:
4624:
4620:
4616:
4612:
4606:
4604:
4600:
4599:
4597:
4596:
4590:
4583:
4576:
4572:
4568:
4564:
4558:
4551:
4546:
4539:
4535:
4531:
4522:
4518:
4514:
4510:
4506:
4501:
4492:
4485:
4478:
4470:
4466:
4462:
4456:
4444:
4434:
4430:
4426:
4422:
4418:
4414:
4410:
4403:
4399:
4389:
4379:
4375:
4371:
4367:
4363:
4359:
4350:
4348:
4342:
4341:
4339:
4338:
4334:
4330:
4325:
4321:
4317:
4313:
4308:
4303:
4298:
4293:
4289:
4285:
4281:
4276:
4271:
4266:
4262:
4258:
4253:
4249:
4244:
4242:
4238:
4237:
4235:
4234:
4228:
4223:
4219:
4215:
4211:
4207:
4203:
4199:
4195:
4190:
4186:
4181:
4177:
4173:
4169:
4165:
4161:
4156:
4154:
4150:
4149:
4143:
4141:
4140:
4133:
4126:
4118:
4112:
4111:
4106:
4101:
4096:
4089:
4088:External links
4086:
4085:
4084:
4077:
4072:
4065:
4058:
4055:
4052:
4051:
4039:
4012:
3993:
3964:
3938:
3871:
3828:
3761:
3696:
3669:
3602:
3587:
3569:
3523:
3480:
3467:(2): 361β403.
3447:
3440:
3422:
3409:
3382:
3347:
3334:
3312:
3270:
3263:
3255:Academic Press
3239:
3226:
3182:
3170:
3150:
3119:
3112:
3081:
3074:
3048:
3027:
3006:
2965:
2905:
2887:
2880:
2862:
2855:
2828:
2807:
2776:
2775:
2773:
2770:
2769:
2768:
2763:
2756:
2753:
2713:
2710:
2687:greenhouse gas
2644:
2641:
2609:
2608:
2548:
2545:
2521:
2520:
2504:
2501:
2500:
2499:
2489:
2483:
2461:
2458:
2457:
2456:
2412:Weinreb amides
2342:
2339:
2320:
2319:
2294:
2293:
2264:
2263:
2235:-sulfonic acid
2231:hydroxylamine-
2201:
2200:
2139:
2138:
2129:
2095:
2092:
2058:
2057:
2026:
2007:O β NH(OH)(OSO
1958:
1957:
1934:respectively:
1895:
1892:
1891:
1890:
1839:
1838:
1762:liquid ammonia
1750:
1749:
1711:
1646:
1645:
1534:
1531:
1530:
1529:
1451:
1448:
1424:
1421:
1399:Lobry de Bruyn
1374:
1371:
1312:hydroxyammonia
1303:
1300:
1299:
1294:
1272:
1271:
1267:standard state
1264:
1261:
1260:
1258:
1257:
1255:-sulfonic acid
1251:Hydroxylamine-
1248:
1236:
1224:
1219:
1214:
1209:
1203:
1201:
1198:
1195:
1194:
1192:
1191:
1186:
1181:
1175:
1173:
1170:
1167:
1166:
1162:
1161:
1156:
1149:
1148:
1145:
1136:
1134:
1131:
1130:
1123:
1122:
1119:
1112:
1109:
1108:
1105:
1099:
1098:
1088:
1081:
1074:
1059:
1058:
1057:
1056:
1054:
1045:
1044:
958:P305+P351+P338
895:
890:
887:
886:
841:
836:
833:
832:
827:
822:
819:
818:
791:
786:
783:
782:
772:
771:
767:
766:
763:
757:
751:
743:
740:
739:
736:
730:
719:
716:
715:
712:
700:
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691:
688:
683:
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679:
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541:
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523:
513:
508:
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500:
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496:
493:
485:
484:
483:
480:
479:
477:
476:
472:
469:
468:
466:
462:
459:
458:
450:
449:
448:
445:
444:
442:
441:
428:
426:
414:
411:
410:
408:
407:
399:
397:
391:
390:
388:
387:
383:
381:
375:
374:
372:
371:
363:
361:
353:
350:
349:
342:
336:
335:
333:
332:
324:
322:
316:
315:
312:
307:
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168:
165:
164:
162:
161:
153:
151:
146:
143:
142:
138:
137:
134:
133:
132:Nitrinous acid
130:
127:
124:
121:
120:Hydroxyammonia
118:
115:
111:
110:
106:
105:
101:
100:
94:
93:
90:
84:
83:
79:
78:
70:
69:
66:
65:
55:
38:Hydroxylamine
26:
24:
18:Hydroxylamines
14:
13:
10:
9:
6:
4:
3:
2:
4877:
4866:
4863:
4861:
4858:
4856:
4853:
4851:
4848:
4846:
4843:
4841:
4838:
4836:
4833:
4832:
4830:
4816:
4811:
4810:
4804:
4799:
4798:
4792:
4788:
4784:
4780:
4775:
4774:
4768:
4766:
4762:
4756:
4750:
4748:
4742:
4740:
4734:
4732:
4726:
4724:
4717:
4715:
4705:
4703:
4696:
4694:
4688:
4686:
4680:
4678:
4672:
4670:
4664:
4662:
4656:
4654:
4648:
4646:
4640:
4637:
4636:
4629:
4627:
4621:
4619:
4613:
4611:
4608:
4607:
4605:
4601:
4595:
4579:
4565:
4563:
4552:
4550:
4542:
4532:
4530:
4526:
4519:
4517:
4507:
4505:
4497:
4481:
4474:
4471:
4469:
4463:
4461:
4449:
4437:
4431:
4429:
4419:
4417:
4406:
4400:
4398:
4394:
4382:
4376:
4374:
4364:
4362:
4355:
4352:
4351:
4349:
4347:
4343:
4337:
4331:
4329:
4326:
4324:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4290:
4288:
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4265:
4259:
4257:
4254:
4252:
4246:
4245:
4243:
4239:
4232:
4231:
4224:
4222:
4216:
4214:
4208:
4206:
4196:
4194:
4187:
4185:
4182:
4180:
4174:
4172:
4166:
4164:
4158:
4157:
4155:
4151:
4146:
4139:
4134:
4132:
4127:
4125:
4120:
4119:
4116:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4091:
4087:
4082:
4078:
4076:
4073:
4070:
4066:
4064:
4063:Hydroxylamine
4061:
4060:
4056:
4049:Sigma-Aldrich
4048:
4043:
4040:
4035:
4031:
4027:
4023:
4016:
4013:
4009:
4005:
4002:
3997:
3994:
3989:
3983:
3975:
3971:
3967:
3961:
3957:
3953:
3949:
3942:
3939:
3934:
3930:
3925:
3920:
3916:
3912:
3907:
3902:
3898:
3894:
3890:
3886:
3882:
3875:
3872:
3867:
3863:
3859:
3855:
3851:
3847:
3843:
3839:
3832:
3829:
3824:
3820:
3815:
3810:
3806:
3802:
3797:
3792:
3788:
3784:
3780:
3776:
3772:
3765:
3762:
3757:
3753:
3748:
3743:
3739:
3735:
3731:
3727:
3723:
3719:
3715:
3711:
3707:
3700:
3697:
3684:
3680:
3673:
3670:
3665:
3661:
3656:
3651:
3647:
3643:
3638:
3633:
3629:
3625:
3621:
3617:
3613:
3606:
3603:
3598:
3594:
3590:
3584:
3580:
3573:
3570:
3565:
3561:
3557:
3553:
3549:
3545:
3541:
3537:
3530:
3528:
3524:
3519:
3515:
3511:
3507:
3503:
3499:
3495:
3491:
3484:
3481:
3475:
3470:
3466:
3462:
3458:
3451:
3448:
3443:
3437:
3433:
3426:
3423:
3419:
3413:
3410:
3405:
3401:
3397:
3393:
3386:
3383:
3378:
3374:
3370:
3366:
3363:(8): 1302β4.
3362:
3358:
3351:
3348:
3337:
3335:9780081009710
3331:
3327:
3326:
3319:
3317:
3313:
3308:
3304:
3300:
3296:
3292:
3288:
3284:
3277:
3275:
3271:
3266:
3260:
3256:
3252:
3251:
3243:
3240:
3236:
3230:
3227:
3222:
3218:
3213:
3208:
3204:
3200:
3196:
3192:
3191:
3186:
3174:
3171:
3163:
3162:
3154:
3151:
3147:
3136:
3132:
3131:
3123:
3120:
3115:
3109:
3105:
3101:
3097:
3096:
3088:
3086:
3082:
3077:
3075:9780470132401
3071:
3067:
3063:
3059:
3052:
3049:
3045:
3041:
3037:
3031:
3028:
3024:
3020:
3016:
3010:
3007:
3003:
2999:
2998:hydroxylamine
2995:
2991:
2987:
2983:
2979:
2975:
2969:
2966:
2961:
2957:
2952:
2947:
2943:
2939:
2935:
2931:
2927:
2923:
2919:
2912:
2910:
2906:
2902:
2896:
2894:
2892:
2888:
2883:
2877:
2873:
2866:
2863:
2858:
2856:0-8493-0487-3
2852:
2848:
2844:
2843:
2835:
2833:
2829:
2824:
2818:
2810:
2804:
2800:
2796:
2792:
2789:. Cambridge:
2788:
2781:
2778:
2771:
2767:
2764:
2762:
2759:
2758:
2754:
2752:
2750:
2746:
2742:
2737:
2735:
2723:
2719:
2711:
2709:
2707:
2703:
2699:
2695:
2690:
2688:
2684:
2683:nitrous oxide
2680:
2679:
2675:
2672:found in the
2671:
2667:
2663:
2661:
2657:
2642:
2640:
2636:
2632:
2630:
2626:
2622:
2618:
2615:developed by
2614:
2603:
2599:
2598:
2597:
2595:
2591:
2590:bacteriophage
2587:
2583:
2579:
2574:
2569:
2565:
2561:
2557:
2552:
2546:
2544:
2542:
2538:
2534:
2530:
2526:
2516:
2511:
2507:
2506:
2502:
2497:
2496:Cope reaction
2493:
2490:
2487:
2484:
2482:
2478:
2477:Hydrogenation
2475:
2474:
2473:
2471:
2467:
2459:
2448:
2447:
2446:
2438:
2434:
2426:
2422:
2420:
2415:
2413:
2409:
2407:
2403:
2398:
2397:calicheamicin
2394:
2390:
2386:
2382:
2378:
2374:
2370:
2362:
2358:
2353:
2348:
2340:
2338:
2329:
2325:
2324:isomerisation
2299:
2298:
2297:
2273:
2272:
2271:
2269:
2261:
2240:
2239:
2238:
2236:
2234:
2228:
2216:
2214:
2210:
2205:
2198:
2188:
2180:
2172:
2164:
2163:
2162:
2160:
2156:
2152:
2130:
2117:
2116:
2115:
2113:
2109:
2105:
2101:
2100:electrophiles
2093:
2091:
2089:
2085:
2080:
2078:
2074:
2070:
2066:
2062:
2027:
1975:
1974:
1973:
1971:
1967:
1963:
1937:
1936:
1935:
1933:
1920:
1916:
1912:
1908:
1904:
1903:hydrochloride
1900:
1894:Other methods
1893:
1888:
1872:
1852:
1844:
1843:
1842:
1827:
1803:
1790:
1789:
1788:
1786:
1767:
1763:
1712:
1692:O β NH(OH)(SO
1673:
1672:
1671:
1655:
1651:
1630:
1618:
1598:
1597:
1596:
1594:
1591:-disulfonate
1590:
1586:
1582:
1573:
1559:
1555:
1552:
1548:
1532:
1510:
1503:
1498:
1497:
1496:
1494:
1491:
1487:
1483:
1482:hydrogenation
1467:
1464:
1463:sulfuric acid
1449:
1447:
1445:
1434:
1430:
1422:
1420:
1404:
1400:
1396:
1395:ethyl nitrate
1392:
1388:
1384:
1380:
1372:
1370:
1368:
1367:nitrification
1364:
1355:
1351:
1347:
1343:
1340:
1334:
1328:
1325:
1321:
1317:
1313:
1309:
1308:Hydroxylamine
1297:
1290:
1285:
1268:
1262:
1256:
1254:
1249:
1247:
1245:
1241:
1237:
1235:
1233:
1229:
1225:
1223:
1220:
1218:
1215:
1213:
1210:
1208:
1205:
1204:
1202:
1197:
1196:
1190:
1187:
1185:
1182:
1180:
1177:
1176:
1174:
1169:
1168:
1163:
1160:
1157:
1154:
1151:
1150:
1146:
1142:
1133:
1132:
1128:
1124:
1120:
1117:
1111:
1110:
1106:
1104:
1101:
1100:
1093:
1086:
1079:
1055:
1052:
1051:
1047:
1046:
896:
893:
889:
888:
842:
839:
835:
834:
831:
828:
825:
821:
820:
816:
811:
806:
801:
796:
792:
789:
785:
784:
780:
778:
773:
768:
765:β39.9 kJ/mol
764:
756:
748:
742:
741:
737:
729:
724:
718:
717:
713:
708:
703:
702:Heat capacity
699:
698:
693:
689:
686:
685:Dipole moment
682:
681:
677:
673:
670:
667:
663:
662:
658:
655:
651:
650:
645:
641:
635:
631:
628:
627:
615:
609:
605:
602:
601:
597:
595:
594:
589:
588:
584:
581:
577:
576:
572:
570:
569:Boiling point
567:
566:
562:
560:
559:Melting point
557:
556:
552:
550:
547:
546:
542:
539:
538:
531:
529:
526:
525:
514:
511:
507:
506:
501:
492:
488:
481:
467:
457:
453:
446:
438:
434:
433:DTXSID7041043
430:
429:
427:
417:
413:
412:
405:
401:
400:
398:
396:
393:
392:
385:
384:
382:
380:
377:
376:
369:
365:
364:
362:
356:
352:
351:
347:
346:Hydroxylamine
343:
341:
338:
337:
330:
326:
325:
323:
321:
318:
317:
313:
310:
306:
305:
298:
297:
295:
293:
288:
287:
283:
279:
276:
274:
272:ECHA InfoCard
269:
268:
261:
257:
256:
254:
252:
249:
248:
241:
240:ChEMBL1191361
237:
236:
234:
232:
229:
228:
221:
217:
216:
214:
212:
209:
208:
201:
197:
196:
194:
191:
190:
183:
179:
178:
176:
172:
167:
166:
159:
155:
154:
152:
149:
145:
144:
139:
131:
129:Hydroxylazane
128:
125:
122:
119:
116:
113:
112:
107:
99:
95:
89:
85:
80:
76:
71:
60:
56:
50:
46:
45:
41:
33:
19:
4855:Rocket fuels
4813:(a strongly
4807:
4795:
4782:
4771:
4631:
4226:
4188:
4080:
4068:
4042:
4025:
4021:
4015:
3996:
3947:
3941:
3888:
3884:
3874:
3841:
3838:Biochemistry
3837:
3831:
3778:
3774:
3764:
3713:
3709:
3699:
3687:. Retrieved
3682:
3672:
3619:
3615:
3605:
3578:
3572:
3539:
3535:
3493:
3489:
3483:
3464:
3460:
3450:
3431:
3425:
3417:
3412:
3395:
3391:
3385:
3360:
3356:
3350:
3339:. Retrieved
3324:
3293:(1): 41β53.
3290:
3286:
3249:
3242:
3234:
3229:
3194:
3188:
3173:
3160:
3153:
3145:
3138:. Retrieved
3129:
3122:
3093:
3057:
3051:
3043:
3042:, series 3,
3039:
3030:
3022:
3018:
3009:
3001:
2997:
2993:
2989:
2988:Hydroxylamin
2985:
2981:
2977:
2968:
2925:
2921:
2900:
2871:
2865:
2840:
2786:
2780:
2738:
2715:
2691:
2676:
2664:
2646:
2643:Biochemistry
2637:
2633:
2610:
2593:
2573:Ernst Freese
2567:
2553:
2550:
2540:
2522:
2463:
2424:
2423:
2416:
2405:
2401:
2388:
2384:
2380:
2376:
2372:
2366:
2360:
2356:
2321:
2295:
2265:
2232:
2225:reacts with
2217:
2206:
2202:
2157:produces an
2140:
2097:
2088:water plasma
2081:
2065:nitromethane
2059:
2042:O] β [NH
1962:nitrous acid
1959:
1899:Julius Tafel
1897:
1840:
1751:
1647:
1588:
1584:
1536:
1486:nitric oxide
1453:
1444:biochemistry
1426:
1376:
1311:
1307:
1306:
1252:
1243:
1239:
1231:
1227:
1126:
1114:Autoignition
1049:
829:
776:
754:
727:
706:
633:
607:
592:
379:RTECS number
141:Identifiers
126:Hydroxyazane
123:Hydroxyamine
109:Other names
91:Azinous acid
3716:(1): 6675.
2994:zu nennen."
2992:Oxyammoniak
2694:asparaginyl
2685:, a potent
2537:caprolactam
2492:Amine oxide
2369:substituted
2328:amine oxide
2123:OH β RβOβNH
1990:β N(OH)(OSO
1915:nitric acid
1828:+ 6 [NH
1727:O β [NH
1714:2 NH(OH)(SO
1523:OH][HSO
1519:β 2 [NH
1474:OH][HSO
1339:hygroscopic
1141:median dose
1127:Lethal dose
1116:temperature
1103:Flash point
824:Signal word
540:Appearance
503:Properties
278:100.029.327
220:CHEBI:15429
4829:Categories
3689:9 December
3398:(4): 476.
3341:2023-08-28
3113:3527306730
3002:oxyammonia
2772:References
2766:Amino acid
2666:Cytochrome
2560:nucleobase
2486:Alkylating
2355:Secondary
2345:See also:
2102:, such as
2038:) + [H
2029:NH(OH)(OSO
1650:hydrolyzed
1631:+ N(OH)(SO
1480:), by the
1423:Production
788:Pictograms
690:0.67553 D
647:Structure
528:Molar mass
404:2FP81O2L9Z
251:ChemSpider
169:3D model (
148:CAS Number
88:IUPAC name
32:hemiaminal
3982:cite book
3915:0027-8424
3858:0006-2960
3805:0027-8424
3738:2041-1723
3646:0027-8424
3597:851813793
3556:0022-2836
3510:1360-1385
3307:0950-4230
2942:1097-0134
2847:CRC Press
2817:cite book
2718:explosive
2668:P460, an
2556:mutations
2460:Synthesis
2268:detonator
2199:solution)
2185:C=NβOH +
2094:Reactions
2046:OH] + HSO
1970:bisulfite
1493:catalysts
1354:oxidation
1318:with the
1217:Hydrazine
1159:ICSC 0661
1030:P403+P233
994:P333+P313
990:P332+P313
962:P308+P313
954:P304+P340
950:P302+P352
946:P301+P312
779:labelling
747:formation
721:Std molar
386:NC2975000
299:232-259-2
291:EC Number
158:7803-49-8
4580: /
4543: /
4527: /
4498: /
4482: /
4475: /
4450: /
4438: /
4407: /
4395: /
4383: /
4356: /
4256:>C=NR
4153:Hydrides
4145:Nitrogen
4004:Archived
3933:27856762
3823:31209050
3756:34795260
3683:PombeNet
3518:16406304
3461:Polymers
3377:20449284
3221:38378822
3212:10879522
2960:24523098
2755:See also
2629:ketoxime
2621:Celanese
2594:in vitro
2568:in vitro
2564:cytidine
2535:to give
2419:nitrones
2387:‑
2322:Partial
2254:βOβS(=O)
2246:βCl + NH
2242:HOβS(=O)
2229:to give
2151:aldehyde
2149:with an
2132:RβX + NH
2119:RβX + NH
2112:nitrogen
1951:OH + 2 H
1853:+ NaO(CH
1832:] + 2 NH
1812:O + 6 NH
1675:N(OH)(SO
1652:to give
1608:] + 2 SO
1604:][NO
1490:platinum
1342:crystals
1314:) is an
1050:NFPA 704
770:Hazards
630:Basicity
585:Soluble
4603:Halides
4241:Organic
4147:species
3924:5187719
3893:Bibcode
3866:8369308
3814:6613137
3783:Bibcode
3747:8602370
3718:Bibcode
3664:4943557
3624:Bibcode
3564:7042980
2951:4133332
2749:mutagen
2698:glycine
2658:(AMO).
2617:Hoechst
2529:Nylon 6
2470:nitrone
2433:organyl
2429:RβNHβOH
2326:to the
2250:OH β NH
2213:ligands
2175:[NH
2114:atoms:
2110:or the
2016:) + HSO
1981:+ 2 HSO
1907:sulfate
1847:[NH
1785:ammonia
1770:[NH
1723:) + 2 H
1701:) + HSO
1657:[NH
1625:[NH
1600:[NH
1558:reduced
1551:aqueous
1545:is the
1470:[NH
1436:[NH
1433:cations
1373:History
1350:Nylon-6
1289:what is
1287: (
1207:Ammonia
723:entropy
618:[NH
604:Acidity
598:β0.758
549:Density
522:
355:PubChem
4817:oxide)
4815:acidic
4346:Oxides
3974:927171
3972:
3962:
3931:
3921:
3913:
3864:
3856:
3821:
3811:
3803:
3754:
3744:
3736:
3662:
3655:389612
3652:
3644:
3595:
3585:
3562:
3554:
3516:
3508:
3438:
3375:
3332:
3305:
3261:
3219:
3209:
3140:5 June
3110:
3072:
2958:
2948:
2940:
2878:
2853:
2805:
2670:enzyme
2625:ketone
2479:of an
2437:amines
2305:OH β N
2279:OH + O
2258:βOH +
2155:ketone
2108:oxygen
1804:+ 4 SO
1752:Solid
1623:O β 2
1352:. The
1284:verify
1281:
1155:(SDS)
830:Danger
674:at N,
616:6.03 (
533:33.030
487:SMILES
329:C00192
231:ChEMBL
200:B01184
192:3DMet
117:Azanol
114:Aminol
82:Names
4785:, 0,
4477:(HON)
4261:-CONR
4071:2001.
3165:(PDF)
2990:oder
2761:Amine
2734:salts
2627:to a
2584:, or
2481:oxime
2454:+ ZnO
2375:- or
2313:+ 3 H
2287:+ 6 H
2283:β 2 N
2179:OH]Cl
2159:oxime
1968:with
1943:+ 3 H
1917:with
1869:OH +
1851:OH]Cl
1808:+ 6 H
1593:anion
1511:+ 2 H
1488:over
1429:salts
1212:Water
678:at O
642:7.97
452:InChI
211:ChEBI
171:JSmol
4744:NHBr
4736:NHCl
4529:ONOO
4358:(NO)
4311:HNCS
4306:HNCO
4301:HOCN
4284:(CN)
4104:MSDS
4047:MSDS
3988:link
3970:PMID
3960:ISBN
3929:PMID
3911:ISSN
3862:PMID
3854:ISSN
3819:PMID
3801:ISSN
3752:PMID
3734:ISSN
3691:2021
3660:PMID
3642:ISSN
3593:OCLC
3583:ISBN
3560:PMID
3552:ISSN
3514:PMID
3506:ISSN
3436:ISBN
3373:PMID
3330:ISBN
3303:ISSN
3259:ISBN
3217:PMID
3142:2014
3108:ISBN
3070:ISBN
2956:PMID
2938:ISSN
2876:ISBN
2851:ISBN
2823:link
2803:ISBN
2722:iron
2503:Uses
2440:RβNH
2389:tert
2309:+ NH
2301:3 NH
2275:4 NH
2197:NaOH
2195:(in
2187:NaCl
2127:+ HX
2079:.
2075:via
2071:and
1947:β NH
1871:NaCl
1865:β NH
1816:β 4
1739:+ SO
1574:and
1504:+ 3
1466:salt
1406:ZnCl
1389:and
1042:P501
1038:P405
1034:P404
1026:P401
1022:P391
1018:P390
1014:P380
1010:P373
1006:P372
1002:P363
998:P362
986:P330
982:P322
978:P321
974:P314
970:P312
966:P310
942:P281
938:P280
934:P273
930:P272
926:P271
922:P270
918:P264
914:P261
910:P260
906:P234
902:P202
898:P201
884:H400
880:H373
876:H351
872:H335
868:H318
864:H317
860:H315
856:H312
852:H302
848:H290
844:H200
676:bent
591:log
395:UNII
340:MeSH
320:KEGG
314:478
4805:,
4752:NHI
4728:NHF
4682:BrN
4674:ClN
4650:NBr
4642:NCl
4638:(?)
4549:NOO
4513:NNO
4473:HNO
4433:HNO
4409:(NO
4378:HNO
4333:-NO
4328:-NO
4296:NCN
4274:HCN
4269:-CN
4233:(?)
4030:doi
3952:doi
3919:PMC
3901:doi
3889:113
3846:doi
3809:PMC
3791:doi
3779:116
3742:PMC
3726:doi
3650:PMC
3632:doi
3544:doi
3540:154
3498:doi
3469:doi
3400:doi
3365:doi
3295:doi
3207:PMC
3199:doi
3100:doi
3062:doi
3000:or
2946:PMC
2930:doi
2795:doi
2611:An
2582:ENU
2578:EMS
2395:in
2335:NβO
2260:HCl
2189:+ H
2181:β R
2171:C=O
2153:or
2067:to
2003:+ H
1977:HNO
1964:or
1939:HNO
1921:or
1919:HCl
1913:of
1905:or
1879:(CH
1731:OH]
1688:+ H
1661:OH]
1619:+ H
1563:HSO
1560:by
1556:is
1484:of
1440:OH]
1414:OH)
1410:(NH
1387:tin
1356:of
777:GHS
758:298
731:298
622:OH]
421:EPA
368:787
358:CID
260:766
4831::
4809:+5
4803:+4
4801:,
4797:+3
4793:,
4791:+2
4789:,
4787:+1
4783:β1
4781:,
4779:β2
4777:,
4773:β3
4723:Cl
4719:NH
4698:NH
4690:IN
4666:FN
4658:NI
4632:NF
4623:NF
4615:NF
4610:NF
4554:NO
4538:NO
4534:HO
4525:NO
4521:HO
4465:NO
4452:NO
4440:NO
4402:NO
4397:NO
4385:NO
4354:NO
4316:CH
4279:CN
4248:NR
4227:NH
4210:HN
4193:OH
4189:NH
4176:NH
4168:NH
4160:NH
4026:48
4024:.
3984:}}
3980:{{
3968:.
3958:.
3927:.
3917:.
3909:.
3899:.
3887:.
3883:.
3860:.
3852:.
3842:32
3840:.
3817:.
3807:.
3799:.
3789:.
3777:.
3773:.
3750:.
3740:.
3732:.
3724:.
3714:12
3712:.
3708:.
3681:.
3658:.
3648:.
3640:.
3630:.
3620:68
3618:.
3614:.
3591:.
3558:.
3550:.
3538:.
3526:^
3512:.
3504:.
3494:11
3492:.
3463:.
3459:.
3396:64
3394:.
3371:.
3361:46
3359:.
3328:.
3315:^
3301:.
3291:16
3289:.
3285:.
3273:^
3253:.
3215:.
3205:.
3195:15
3193:.
3187:.
3144:.
3135:32
3106:.
3084:^
3068:.
3023:10
3021:,
3004:.)
2980:,
2954:.
2944:.
2936:.
2926:82
2924:.
2920:.
2908:^
2890:^
2849:.
2831:^
2819:}}
2815:{{
2751:.
2736:.
2730:OH
2726:NH
2689:.
2649:NH
2596:.
2580:,
2445::
2421:.
2414:.
2399:.
2237::
2223:OH
2219:NH
2215:.
2173:+
2161:.
2147:OH
2143:NH
2090:.
1972::
1928:SO
1887:OH
1875:CH
1873:+
1861:CH
1836:OH
1821:2β
1818:SO
1794:NO
1792:2
1778:SO
1768:,
1764:.
1758:OH
1754:NH
1742:2β
1735:SO
1670::
1665:SO
1614:NH
1612:+
1595::
1577:SO
1549::
1543:OH
1539:NH
1515:SO
1502:NO
1500:2
1459:OH
1455:NH
1446:.
1369:.
1359:NH
1137:50
1135:LD
1040:,
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:,
916:,
912:,
908:,
904:,
900:,
882:,
878:,
874:,
870:,
866:,
862:,
858:,
854:,
850:,
846:,
781::
750:(Ξ
639:)
632:(p
624:)
613:)
606:(p
520:OH
516:NH
494:NO
4754:2
4746:2
4738:2
4730:2
4721:2
4713:2
4711:F
4709:2
4707:N
4702:F
4700:2
4692:3
4684:3
4676:3
4668:3
4660:3
4652:3
4644:3
4634:5
4625:3
4617:2
4591:3
4586:O
4584:2
4582:N
4577:4
4575:O
4573:2
4571:N
4569:4
4567:H
4559:4
4547:2
4545:O
4540:2
4536:2
4523:2
4515:2
4511:2
4509:H
4504:O
4502:2
4500:N
4493:2
4488:O
4486:2
4484:N
4479:2
4467:3
4457:2
4445:3
4435:3
4427:5
4425:O
4423:2
4421:N
4415:2
4413:)
4411:2
4404:2
4390:2
4380:2
4372:3
4370:O
4368:2
4366:N
4360:2
4335:2
4322:2
4320:N
4318:2
4294:2
4292:H
4286:2
4263:2
4250:3
4229:5
4220:3
4218:N
4212:3
4204:4
4202:H
4200:2
4198:N
4191:2
4184:N
4178:2
4170:4
4162:3
4137:e
4130:t
4123:v
4036:.
4032::
4010:.
3990:)
3976:.
3954::
3935:.
3903::
3895::
3868:.
3848::
3825:.
3793::
3785::
3758:.
3728::
3720::
3693:.
3666:.
3634::
3626::
3599:.
3566:.
3546::
3520:.
3500::
3477:.
3471::
3465:5
3444:.
3406:.
3402::
3379:.
3367::
3344:.
3309:.
3297::
3267:.
3223:.
3201::
3183:2
3116:.
3102::
3078:.
3064::
3044:6
2982:8
2962:.
2932::
2884:.
2859:.
2825:)
2811:.
2797::
2728:2
2696:-
2651:3
2619:β
2541:3
2539:(
2517:.
2498:)
2452:2
2442:2
2425:N
2406:O
2404:,
2402:N
2385:N
2381:N
2377:N
2373:O
2361:N
2359:,
2357:N
2333:3
2331:H
2317:O
2315:2
2311:3
2307:2
2303:2
2291:O
2289:2
2285:2
2281:2
2277:2
2256:2
2252:2
2248:2
2244:2
2233:O
2221:2
2193:O
2191:2
2183:2
2177:3
2169:2
2167:R
2145:2
2134:2
2125:2
2121:2
2052:4
2049:β
2044:3
2040:3
2035:2
2032:β
2022:4
2019:β
2013:2
2010:β
2005:2
2001:2
1999:)
1996:2
1993:β
1987:3
1984:β
1979:2
1955:O
1953:2
1949:2
1945:2
1941:3
1930:4
1926:2
1924:H
1885:3
1883:)
1881:2
1877:3
1867:2
1863:3
1859:3
1857:)
1855:2
1849:3
1834:2
1830:4
1824:4
1814:3
1810:2
1806:2
1800:2
1797:β
1780:4
1776:2
1774:]
1772:4
1756:2
1745:4
1737:4
1733:2
1729:3
1725:2
1720:3
1717:β
1707:4
1704:β
1698:3
1695:β
1690:2
1686:2
1684:)
1681:3
1678:β
1667:4
1663:2
1659:3
1642:2
1640:)
1637:3
1634:β
1629:]
1627:4
1621:2
1616:3
1610:2
1606:2
1602:4
1589:N
1587:,
1585:N
1579:2
1569:3
1566:β
1541:2
1527:]
1525:4
1521:3
1517:4
1513:2
1508:2
1506:H
1478:]
1476:4
1472:3
1457:2
1438:3
1416:2
1412:2
1408:2
1361:3
1335:H
1333:O
1330:2
1327:H
1324:N
1279:N
1253:O
1244:N
1242:,
1240:N
1232:O
1230:,
1228:N
1143:)
1139:(
1091:3
1084:1
1077:2
760:)
755:H
752:f
733:)
728:S
726:(
709:)
707:C
705:(
637:b
634:K
620:3
611:a
608:K
593:P
518:2
423:)
419:(
173:)
34:.
20:)
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