1235:
1859:) (Fourcroy and Vauquelin, 1806), p. 543; (Chevreul, 1809), p. 129) â to combust completely even in the absence of air (because even in the absence of air, heat could transform it completely into gases, leaving no carbon). ((Fourcroy and Vauquelin, 1806), pp. 542â543); (Chevreul, 1809), pp. 127â128) However, when picric acid was burned, the heat that was generated caused some of the acid to evaporate, dissipating so much heat that only burning, not detonation, occurred. In contrast, picrate salts were solids that did not sublimate, and thus did not dissipate heat; hence, they did detonate.((Fourcroy and Vauquelin, 1806), p. 542); (Chevreul, 1809), pp. 129â130) See:
1147:
369:
268:
713:
619:
614:
54:
624:
709:
45:
63:
714:
874:
1032:, and the correct determination of its formula, were accomplished during 1841. In 1799, French chemist Jean-Joseph Welter (1763â1852) produced picric acid by treating silk with nitric acid; he found that potassium picrate could explode. Not until 1830 did chemists think to use picric acid as an
1569:
salts that are even more sensitive and hazardous than the acid itself. Industrially, picric acid is especially hazardous because it is volatile and slowly sublimes even at room temperature. Over time, the buildup of picrates on exposed metal surfaces can constitute an explosion hazard.
712:
1745:: 114â130. See pages 127â130: "A method of dying wool and silk, of a yellow colour, with indigo; and also with several other blue and red colouring substances." and "Receipt for making the yellow dye." â where Woulfe treats indigo with nitric acid ("acid of nitre").
1253:, facility using processes developed by his chemists. He built two plants with a capacity of six tons of phenol per day. Production began the first week of September, one month after hostilities began in Europe. He built two plants to produce the raw material
1573:
Picric acid gauze, if found in antique first aid kits, presents a safety hazard because picric acid of that vintage (60â90 years old) will have become crystallized and unstable, and may have formed metal picrates from long storage in a metal first aid case.
1230:
began manufacturing synthetic phenol in 1915, with Dow being the main producer. Dow describes picric acid as "the main battlefield explosive used by the French. Large amounts also went to Japan, where it was made into picric acid sold to the
Russians."
1301:
is activated towards electrophilic substitution reactions, and attempted nitration of phenol, even with dilute nitric acid, results in the formation of high molecular weight tars. In order to minimize these side reactions, anhydrous phenol is
1178:
was less readily available than phenol, and TNT is less powerful than picric acid, but the improved safety of munitions manufacturing and storage caused the replacement of picric acid by TNT for most military purposes between the World Wars.
1910:
Sprengel filed patents in
Britain for "safety explosives" (i.e., stable explosives) on April 6, 1871 (no. 921), and on October 5, 1871 (no. 2642); in the latter patent, Sprengel proposed using picric acid dissolved in nitric acid as an
1374:(which is produced in a similar process to picric acid but with toluene as the feedstock). Picramide, formed by aminating picric acid (typically beginning with Dunnite), can be further aminated to produce the very stable explosive
1469:
are combined and heated, a characteristic red color forms. With a calibrating glucose solution, the red color can be used to measure the glucose levels added. This is known as the Lewis and
Benedict method of measuring glucose.
1822:(The next day, I found the crucible covered with golden crystals which had the fineness of silk, which detonated like gun powder, and which, in my opinion, would produce the same effect in a firearm.) Welter named picric acid
730:
594:
1820:"Le lendemain je trouvai la capsule tapisée de cristaux dorés qui avoient la finesse de la soie, qui détonoient comme la poudre à canon, et qui, à mon avis, en auroient produit l'effet dans une arme à feu."
2453:
1580:
units are often called to dispose of picric acid if it has dried out. In the United States there was an effort to remove dried picric acid containers from high school laboratories during the 1980s.
2435:
1478:
Much less commonly, wet picric acid has been used as a skin dye, or temporary branding agent. It reacts with proteins in the skin to give a dark brown color that may last as long as a month.
1940:, 2nd ed. (London: Eyre & Spottiswoode, 1903). This pamphlet is a collection of (splenetic) letters in which Sprengel defends his priority in the use of picric acid as a high explosive.
165:
2243:
Hydrogen
Bonding and Electron Donor-Acceptor (EDA) Interactions Controlling the Crystal Packing of Picric Acid and Its Adducts with Nitrogen Bases. Their Rationalization in Terms of the p
1105:
which, instead of attempting to stabilize the material itself, removed its contact with metal by coating the inside of the shells with layer(s) of resin and wax. In 1889, a mixture of
1401:
grain boundaries in ferritic steels. The hazards associated with picric acid have meant it has largely been replaced with other chemical etchants. However, it is still used to etch
1721:
1699:
789:
1951:
Koike, Shigeki (2006). "The Russo-Japanese War and the system of SHIMOSE gunpowder" (PDF). Bulletin of Papers (in
Japanese). Takasaki City University of Economics. 1 (49).
887:
1381:
It has found some use in organic chemistry for the preparation of crystalline salts of organic bases (picrates) for the purpose of identification and characterization.
1458:
Picric acid forms red isopurpurate with hydrogen cyanide (HCN). By photometric measurement of the resulting dye, picric acid can be used to quantify hydrogen cyanide.
715:
1234:
2461:
2373:
Junqueira LC, Bignolas G, Brentani RR (1979). "Picrosirius staining plus polarization microscopy, a specific method for collagen detection in tissue sections".
418:
1865:"Mémoire sur la découverte d'une nouvelle matiÚre inflammable et détonnante, formée par l'action de l'acide nitrique sur l'indigo et les matiÚres animales"
2432:
2191:
1131:) was used by the United States beginning in 1906. However, shells filled with picric acid become unstable if the compound reacts with the metal shell or
737:
2550:
1613:
1867:[Memoir on the discovery of a new flammable and explosive substance, formed by the action of nitric acid on indigo and animal substances].
2302:
2277:
2525:
1844:
638:
1598:
as these materials are water-soluble. Currently there are various fluorescent probes to sense and detect picric acid in very minute quantity.
664:
2285:
2081:
1671:
1553:
Modern safety precautions recommend storing picric acid wet, to minimize the danger of explosion. Dry picric acid is relatively sensitive to
1250:
684:
1338:, while both acetic acid and carbon dioxide are lost from the latter. Another method of picric acid synthesis is direct nitration of
2699:
2201:
2144:
2123:
2102:
2060:
1970:
383:
1914:
Hermann
Sprengel (1873) "On a new class of explosives which are non-explosive during their manufacture, storage, and transport",
1594:
that contain such munitions not be disturbed in any way. The hazard may subside when the shells become corroded enough to admit
575:
2620:"Protonation and axial ligation intervened fluorescence turn-off sensing of picric acid in freebase and tin(iv) porphyrins"
1907:
In March 1871, Sprengel detonated picric acid at the gunpowder works of John Hall & Sons in
Faversham in Kent, England.
853:
680:
2719:
1146:
658:
316:
1843:
A theory to explain why picrate salts detonated whereas picric acid itself didn't, was proposed by the French chemists
1590:. The buildup of metal picrates over time renders them shock-sensitive and extremely hazardous. It is recommended that
668:
1523:
347:
1289:. Wartime shortages made these ventures profitable. In 1915, his production capacity was fully committed by midyear.
2408:
723:
1881:
1805:
1655:
894:
813:
800:
538:
1852:
1514:
from that period as a burn treatment. It was notably used for the treatment of burns suffered by victims of the
2156:
Conot, Robert (1979), A Streak of Luck: The Life & Legend of Thomas Alva Edison, Seaview Books, NY, p 413-4
1756:
1075:
in an artillery barrel at the time of firing. In 1885, based on research of
Hermann Sprengel, French chemist
618:
613:
1884:[Extract from a memoir on the bitter substances formed by the reaction of nitric acid with indigo].
1848:
1258:
557:
1934:
263:
2729:
2334:"Picrosirius Red Staining: A Useful Tool to Appraise Collagen Networks in Normal and Pathological Tissues"
1998:
1806:"Sur quelques matiÚres particuliÚres, trouvées dans les substances animals, traitées par l'acide nitrique"
2558:
2020:
1882:"Extrait d'un mémoire sur les substances amÚres formées par la réaction de l'acide nitrique sur l'indigo"
205:
2724:
1139:
which are more sensitive than the parent phenol. The sensitivity of picric acid was demonstrated by the
1123:. By 1894 Russia was manufacturing artillery shells filled with picric acid. Ammonium picrate (known as
1106:
985:
632:
623:
606:
87:
2310:
1855:
in 1809. Picric acid evidently contained enough oxygen within itself â i.e. it was "super-oxygenated" (
2483:
2631:
1607:
1417:
1307:
1195:
75:
2619:
2663:
Cleanup of
Chemical and Explosive Munitions: Location, Identification and Environmental Remediation
1864:
1783:
1623:
1515:
1025:
843:
364:
131:
2254:
2025:
1994:
1565:, rendering it safe. Glass or plastic bottles are required, as picric acid can easily form metal
1278:
1163:
1155:
1033:
965:
2695:
2679:
2390:
2355:
2281:
2197:
2140:
2119:
2098:
2077:
2056:
1976:
1966:
1808:[On some particular materials, found in animal substances, treated with nitric acid].
1667:
1554:
1339:
1262:
1191:
1140:
1009:
1735:
1652:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1370:
salt of picric acid. Dunnite is more powerful but less stable than the more common explosive
1087:. In 1887 the French government adopted a mixture of picric acid and guncotton with the name
2639:
2382:
2345:
1923:
1659:
1562:
1466:
1076:
1056:
1041:
1037:
910:
517:
441:
325:
2439:
1402:
1335:
1171:
1159:
1120:
1084:
225:
53:
2635:
2498:
368:
267:
185:
141:
1448:
1413:
1393:, a 4% picric acid in ethanol etch, termed "picral", has been commonly used in optical
1334:
can also be used to mitigate tar formation. Carbon dioxide is lost from the former via
1331:
1315:
1110:
1101:
1068:
1064:
1049:
942:
865:
528:
2166:
2713:
1628:
1577:
1511:
1394:
1319:
1242:
1080:
506:
496:
256:
2332:
Lattouf R, Younes R, Lutomski D, Naaman N, Goudeau G, Senni K, Changotade S (2014).
1150:
Workers filling shells with liquid melinite at a French munitions factory during WWI
688:
1286:
1266:
1227:
1211:
1005:
1113:, or an ammonium salt of trinitrocresol, started to be manufactured with the name
2580:
289:
2670:
Brown, David K.; McCallum, Iain (2001). "Ammunition Explosions in World War I".
1663:
1545:
for use as fishing lures. Its popularity has been tempered by its toxic nature.
1542:
1527:
1519:
1363:
1311:
1215:
1207:
1187:
1167:
1128:
773:
749:
1238:
Photograph showing the use of picric acid on a farm to remove stumps and rocks.
44:
2704:
2218:
1695:
1487:
1452:
1432:
1425:
1390:
1359:
1323:
1303:
1246:
1072:
997:
981:
969:
930:
676:
468:
216:
17:
2683:
2350:
2333:
2259:
1326:, and careful temperature control is required. Synthesis routes that nitrate
1980:
1713:
1618:
1591:
1583:
1538:
1534:
1424:
specimens. It improves the staining of acid dyes, but it can also result in
1421:
1398:
1270:
1060:
1059:
widely considered suitable to withstand the shock of firing in conventional
989:
961:
336:
2359:
1486:
During the early 20th century, picric acid was stocked in pharmacies as an
1071:(guncotton) were available earlier, but shock sensitivity sometimes caused
1052:
material. A full synthesis was later found by Leonid Valerieovich Kozakov.
62:
1936:
The Discovery of Picric Acid (Melinite, Lyddite) "As a Powerful Explosive"
646:
2412:
1927:
1595:
1587:
1558:
1503:
1436:
1367:
1223:
1115:
1045:
736:
729:
722:
695:
236:
2394:
245:
2643:
2386:
1566:
1495:
1462:
1327:
1282:
1254:
1219:
1199:
1175:
1136:
957:
486:
276:
1455:. It forms a colored complex that can be measured using spectroscopy.
1610:, an explosive containing picric acid, formerly used in naval shells.
1499:
1461:
During the early 20th century, picric acid was used to measure blood
1310:, and the resulting sulfonic acid is then nitrated with concentrated
1298:
1274:
1183:
1099:. Japan followed with an alternative stabilization approach known as
1029:
196:
31:
1202:) to keep it from the Allies. At the time, phenol was obtained from
953:), meaning "bitter", due to its bitter taste. It is one of the most
864:
Except where otherwise noted, data are given for materials in their
672:
642:
392:
InChI=1S/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H
2526:"Potentially explosive substance was in Catlins museum for decades"
1561:, so laboratories that use it store it in bottles under a layer of
1447:
Clinical chemistry laboratory testing utilizes picric acid for the
1091:. In 1888, Britain started manufacturing a very similar mixture in
402:
InChI=1/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H
1507:
1342:
with nitric acid. It crystallizes in the orthorhombic space group
1265:, replacing supplies previously from Germany. Edison manufactured
1233:
1145:
1001:
300:
176:
164:
154:
1249:
records. He responded by undertaking production of phenol at his
2074:
Laclede Gas and St. Louis: 150 Years Working Together, 1857â2007
1491:
1375:
1203:
1132:
1092:
993:
954:
826:
650:
2433:
Quantification of total cyanide content in stone fruit kernels.
1771:"C'est sous ce nom que j'ai désigné l'acide carboazotique, ..."
968:, which is its primary use. It has also been used as medicine (
1773:(It is by this name that I designated carboazotic acid, ... )
1371:
1350:
with a = 9.13 Ă
, b = 18.69 Ă
, c = 9.79 Ă
and α = ÎČ = Îł = 90°.
1718:
Immediately Dangerous to Life or Health Concentrations (IDLH)
1186:, the precursor to picric acid, emphasize its importance in
1040:
of picric acid were explosive, not the acid itself. In 1871
352:
2618:
Arunkumar, Chellaiah; Sujatha, Subramaniam (26 Oct 2015).
511:> 300 °C (572 °F; 573 K) Detonates
1739:
Philosophical Transactions of the Royal Society of London
1194:
to have bought US supplies of phenol and converted it to
1024:). Picric acid was given that name by the French chemist
707:
1218:
reports being asked to expand production of phenol (and
2678:(1). International Naval Research Organization: 58â69.
882:
1055:
Picric acid was the first strongly explosive nitrated
2486:
History of the Great War - Surgery of the War, Vol. 1
1722:
National Institute for Occupational Safety and Health
1700:
National Institute for Occupational Safety and Health
1004:, the synthesis from indigo first being performed by
2190:
Agrawal, Jai Prakash; Hodgson, Robert (2007-01-11).
1079:
patented the use of pressed and cast picric acid in
2250:
Equalization and Electron-Pair Saturation Concepts.
1736:"Experiments to shew the nature of aurum mosaicum,"
1358:By far the greatest use of picric acid has been in
2219:"Manufacture of picric acid. US Patent US1299171A"
2042:. London and New York: Routeladge Classics, p. 98.
1518:in 1937. Picric acid was used as a treatment for
1044:proved it could be detonated and afterwards most
30:"Lyddite" redirects here. For the rock type, see
2409:"Creatinine Direct Procedure, on CimaScientific"
2167:"λ » LambdaSyn â Synthese von PikrinsĂ€ure"
980:Picric acid was probably first mentioned in the
288:
2095:Faith, Hope & $ 5000: The Story of Monsanto
711:
140:
2604:
2602:
1586:containing picric acid may be found in sunken
1170:. Germany began filling artillery shells with
1036:. Before then, chemists assumed that only the
2557:. Irish Times. 1 October 2010. Archived from
2454:"Measuring blood glucose levels in the 1920s"
2338:Journal of Histochemistry & Cytochemistry
1851:in 1806 and reiterated by the French chemist
8:
2705:CDC - NIOSH Pocket Guide to Chemical Hazards
2524:Harding, Evan; Searle, Jamie (7 July 2021).
2137:Growth Company: Dow Chemical's First Century
2116:Growth Company: Dow Chemical's First Century
1965:. Stroud, UK: Sutton Pub. pp. 151â163.
1869:MĂ©moires de l'Institute des Sciences et Arts
1533:Picric acid has been used for many years by
1269:, which had previously been supplied by the
1019:
1013:
501:122.5 °C (252.5 °F; 395.6 K)
2272:Carson, Freida L.; Hladik, Christa (2009).
1759:[Fourth memoir on chemical types].
1757:"QuatriÚme mémoire sur les types chimiques"
1646:
1644:
1322:group is displaced. The reaction is highly
2274:Histotechnology: A Self-Instructional Text
1431:Picric acid is used in the preparation of
367:
266:
224:
36:
2349:
324:
1794:: 195â228; see especially pages 221â228.
1694:NIOSH Pocket Guide to Chemical Hazards.
1614:Table of explosive detonation velocities
2278:American Society for Clinical Pathology
1640:
1182:Efforts to control the availability of
423:
388:
363:
244:
2581:"Unstable chemicals made safe by army"
1689:
1687:
1685:
1683:
1522:suffered by soldiers stationed on the
1465:levels. When glucose, picric acid and
1048:powers used picric acid as their main
257:
2053:The Big Bang: a History of Explosives
1963:The big bang: a history of explosives
1210:ovens and the manufacture of gas for
964:organic compounds, picric acid is an
754:150 °C; 302 °F; 423 K
395:Key: OXNIZHLAWKMVMX-UHFFFAOYSA-N
204:
184:
7:
2301:Llewellyn, Brian D (February 2009).
2217:Green, Arthur George (1919-04-01).
1416:is a common picric-acidâcontaining
405:Key: OXNIZHLAWKMVMX-UHFFFAOYAM
279:
2241:V. Bertolasi, P. Gilli, G. Gilli:
1273:. Other wartime products included
25:
2551:"Bomb squad called to Dublin lab"
1786:(On phenol and its derivatives),
1222:) to assist the war effort. Both
972:, burn treatments) and as a dye.
1886:Annales de Chimie et de Physique
1810:Annales de Chimie et de Physique
1788:Annales de Chimie et de Physique
1761:Annales de Chimie et de Physique
1366:, also known as Dunnite, is the
992:substances such as animal horn,
941:). The name "picric" comes from
872:
622:
617:
612:
61:
52:
43:
2193:Organic Chemistry of Explosives
2021:Dunnite Smashes Strongest Armor
1916:Journal of the Chemical Society
1834:( ... I will name it "bitter".)
1784:"Sur le phényle et ses dérivés"
1318:groups are introduced, and the
868:(at 25 °C , 100 kPa).
473:229.10 g·mol
113:2-Hydroxy-1,3,5-trinitrobenzene
2003:. Hudson-Kimberly. p. 243
2000:The second Boer War, 1899â1900
576:Occupational safety and health
1:
2694:, New York: Wiley-VCH, 1996.
2139:, Michigan State University,
2118:, Michigan State University,
1245:needed phenol to manufacture
794:(US health exposure limits):
1863:Fourcroy; Vauquelin (1806).
1804:Welter, Jean-Joseph (1799).
1154:Picric acid was used in the
1028:in 1841. Its synthesis from
1008:in 1771. The German chemist
988:. Initially, it was made by
780:100 mg/kg (guinea pig, oral)
2587:. RTĂ News. 3 November 2010
1664:10.1039/9781849733069-FP001
1435:, a histological stain for
762:or concentration (LD, LC):
27:Explosive chemical compound
2746:
2661:Albright, Richard (2011).
2093:Forrestal, Dan J. (1977),
1812:. 1st series (in French).
1763:. 3rd series (in French).
1656:Royal Society of Chemistry
1428:of any DNA in the sample.
820:TWA 0.1 mg/m ST 0.3 mg/m
481:Colorless to yellow solid
29:
2375:The Histochemical Journal
2276:(3 ed.). Hong Kong:
2196:. John Wiley & Sons.
946:
862:
848:7,350 m·s at Ï 1.70
837:
788:
784:120 mg/kg (rabbit, oral)
758:
593:
573:
568:
434:
426:O=()c1cc(cc(()=O)c1O)()=O
414:
379:
124:
98:
86:
74:
69:
60:
51:
42:
2351:10.1369/0022155414545787
2097:, Simon & Schuster,
1510:was commonly stocked in
1314:. During this reaction,
659:Precautionary statements
2076:, Laclede Gas Company,
1826:(bitter): from p. 304:
1782:Auguste Laurent (1841)
1490:and as a treatment for
1259:Johnstown, Pennsylvania
1251:Silver Lake, New Jersey
1018:(rendered in French as
558:Magnetic susceptibility
491:1.763 g·cm, solid
111:2,4,6-Trinitro-1-phenol
2692:Explosives Engineering
1239:
1151:
1135:casings to form metal
1095:, Kent, with the name
1020:
1014:
1012:had named picric acid
960:. Like other strongly
718:
92:2,4,6-Trinitrobenzenol
2672:Warship International
2260:doi:10.1021/cg101007a
2258:2011, 11, 2724â2735,
2135:Brandt, E.N. (1997),
2114:Brandt, E.N. (1997),
1658:. 2014. p. 691.
1506:. Picric-acidâsoaked
1385:Optical metallography
1297:The aromatic ring of
1237:
1149:
1015:KohlenstickstoffsÀure
986:Johann Rudolf Glauber
782:250 mg/kg (cat, oral)
717:
88:Systematic IUPAC name
2055:, Sutton Publishing
2051:Brown, G.I. (1998),
1961:Brown, G.I. (1998).
1928:10.1039/js8732600796
1734:Peter Woulfe (1771)
1608:Shellite (explosive)
1541:and feathers a dark
1308:fuming sulfuric acid
1196:acetylsalicylic acid
935:2,4,6-trinitrophenol
700:(fire diamond)
80:2,4,6-Trinitrophenol
76:Preferred IUPAC name
2720:Explosive chemicals
2636:2015RSCAd...593243S
2464:on 16 December 2018
2280:Press. p. 19.
1995:Wisser, John Philip
1516:Hindenburg disaster
1206:as a co-product of
1026:Jean-Baptiste Dumas
1021:acide carboazotique
913:with the formula (O
844:Detonation velocity
518:Solubility in water
39:
2644:10.1039/C5RA18310C
2561:on 22 October 2012
2499:"Picric Acid, Wet"
2438:2019-04-30 at the
2387:10.1007/BF01002772
2255:Cryst. Growth Des.
2223:patents.google.com
2072:Beck, Bill (2007)
2026:The New York Times
1933:Hermann Sprengel,
1828:" ... je nommerai
1755:Dumas, J. (1841).
1420:solution used for
1279:p-phenylenediamine
1240:
1164:Russo-Japanese War
1156:Battle of Omdurman
1152:
1107:ammonium cresylate
895:Infobox references
829:(Immediate danger)
719:
37:
2690:Cooper, Paul W.,
2665:. William Andrew.
2287:978-0-89189-581-7
2171:www.lambdasyn.org
2126:p. 77, 97 and 244
2082:978-0-9710910-1-6
2029:, August 18, 1907
1880:Chevreul (1809).
1673:978-0-85404-182-4
1340:2,4-dinitrophenol
1263:Bessemer, Alabama
1141:Halifax Explosion
1010:Justus von Liebig
903:Chemical compound
901:
900:
633:Hazard statements
564:-84.34·10 cm/mol
348:CompTox Dashboard
166:Interactive image
105:Phenol trinitrate
16:(Redirected from
2737:
2687:
2666:
2648:
2647:
2615:
2609:
2606:
2597:
2596:
2594:
2592:
2577:
2571:
2570:
2568:
2566:
2547:
2541:
2540:
2538:
2536:
2521:
2515:
2514:
2512:
2510:
2495:
2489:
2480:
2474:
2473:
2471:
2469:
2460:. Archived from
2449:
2443:
2430:
2424:
2423:
2421:
2420:
2411:. Archived from
2405:
2399:
2398:
2370:
2364:
2363:
2353:
2329:
2323:
2322:
2320:
2318:
2309:. Archived from
2298:
2292:
2291:
2269:
2263:
2239:
2233:
2232:
2230:
2229:
2214:
2208:
2207:
2187:
2181:
2180:
2178:
2177:
2163:
2157:
2154:
2148:
2133:
2127:
2112:
2106:
2091:
2085:
2070:
2064:
2049:
2043:
2036:
2030:
2018:
2012:
2011:
2009:
2008:
1991:
1985:
1984:
1958:
1952:
1949:
1943:
1922: : 796â808
1902:
1896:
1893:
1876:
1845:Antoine Fourcroy
1841:
1835:
1817:
1801:
1795:
1780:
1774:
1768:
1752:
1746:
1732:
1726:
1725:
1710:
1704:
1703:
1691:
1678:
1677:
1648:
1624:Verhoeff's stain
1467:sodium carbonate
1405:, such as AZ31.
1403:magnesium alloys
1397:to reveal prior
1362:and explosives.
1271:German dye trust
1085:artillery shells
1057:organic compound
1042:Hermann Sprengel
1023:
1017:
948:
911:organic compound
885:
879:
876:
875:
774:lowest published
739:
732:
725:
710:
690:
686:
682:
678:
674:
670:
666:
652:
648:
644:
640:
626:
621:
616:
533:1 mmHg (195 °C)
442:Chemical formula
372:
371:
356:
354:
328:
292:
281:
270:
259:
248:
228:
208:
188:
168:
144:
107:Picronitric acid
65:
56:
47:
40:
21:
2745:
2744:
2740:
2739:
2738:
2736:
2735:
2734:
2710:
2709:
2669:
2660:
2657:
2655:Further reading
2652:
2651:
2617:
2616:
2612:
2607:
2600:
2590:
2588:
2579:
2578:
2574:
2564:
2562:
2549:
2548:
2544:
2534:
2532:
2523:
2522:
2518:
2508:
2506:
2505:. 21 April 1998
2497:
2496:
2492:
2481:
2477:
2467:
2465:
2452:
2450:
2446:
2440:Wayback Machine
2431:
2427:
2418:
2416:
2407:
2406:
2402:
2372:
2371:
2367:
2344:(10): 751â758.
2331:
2330:
2326:
2316:
2314:
2300:
2299:
2295:
2288:
2271:
2270:
2266:
2249:
2240:
2236:
2227:
2225:
2216:
2215:
2211:
2204:
2189:
2188:
2184:
2175:
2173:
2165:
2164:
2160:
2155:
2151:
2134:
2130:
2113:
2109:
2092:
2088:
2071:
2067:
2050:
2046:
2037:
2033:
2019:
2015:
2006:
2004:
1993:
1992:
1988:
1973:
1960:
1959:
1955:
1950:
1946:
1903:
1899:
1879:
1862:
1853:Michel Chevreul
1849:Louis Vauquelin
1842:
1838:
1803:
1802:
1798:
1781:
1777:
1754:
1753:
1749:
1733:
1729:
1712:
1711:
1707:
1693:
1692:
1681:
1674:
1650:
1649:
1642:
1637:
1604:
1551:
1484:
1476:
1445:
1433:Picrosirius red
1411:
1387:
1356:
1349:
1336:decarboxylation
1295:
1174:(TNT) in 1902.
1172:trinitrotoluene
1160:Second Boer War
1121:Austria-Hungary
978:
928:
924:
920:
916:
904:
897:
892:
891:
890: ?)
881:
877:
873:
869:
838:Explosive data
830:
817:
804:
783:
781:
777:
771:
744:
743:
742:
741:
734:
727:
720:
716:
708:
661:
635:
609:
586:
561:
547:
520:
462:
458:
454:
450:
444:
430:
427:
422:
421:
410:
407:
406:
403:
397:
396:
393:
387:
386:
375:
357:
350:
331:
311:
295:
282:
251:
231:
211:
191:
171:
158:
147:
134:
120:
118:
116:
114:
112:
110:
108:
106:
104:
103:Carbazotic acid
102:
94:
93:
82:
81:
35:
28:
23:
22:
15:
12:
11:
5:
2743:
2741:
2733:
2732:
2727:
2722:
2712:
2711:
2708:
2707:
2702:
2688:
2667:
2656:
2653:
2650:
2649:
2630:(113): 93243.
2610:
2608:Albright, p.78
2598:
2572:
2555:irishtimes.com
2542:
2516:
2490:
2475:
2444:
2425:
2400:
2381:(4): 447â455.
2365:
2324:
2313:on 31 May 2015
2293:
2286:
2264:
2247:
2234:
2209:
2202:
2182:
2158:
2149:
2128:
2107:
2086:
2065:
2044:
2031:
2013:
1986:
1971:
1953:
1944:
1942:
1941:
1931:
1912:
1908:
1897:
1895:
1894:
1877:
1836:
1796:
1775:
1747:
1727:
1705:
1679:
1672:
1639:
1638:
1636:
1633:
1632:
1631:
1626:
1621:
1616:
1611:
1603:
1600:
1550:
1547:
1512:first aid kits
1483:
1480:
1475:
1472:
1449:Jaffe reaction
1444:
1441:
1414:Bouin solution
1410:
1407:
1386:
1383:
1355:
1352:
1347:
1332:salicylic acid
1294:
1291:
1190:. Germans are
1111:trinitrocresol
1102:Shimose powder
1069:nitrocellulose
1065:Nitroglycerine
1050:high explosive
1000:, and natural
977:
974:
926:
922:
918:
914:
902:
899:
898:
893:
871:
870:
866:standard state
863:
860:
859:
856:
850:
849:
846:
840:
839:
835:
834:
831:
825:
822:
821:
818:
812:
809:
808:
807:TWA 0.1 mg/m
805:
799:
796:
795:
786:
785:
778:
769:
767:
764:
763:
756:
755:
752:
746:
745:
735:
728:
721:
706:
705:
704:
703:
701:
692:
691:
685:P370+P380+P375
662:
657:
654:
653:
636:
631:
628:
627:
610:
605:
602:
601:
591:
590:
587:
584:
581:
580:
571:
570:
566:
565:
562:
556:
553:
552:
549:
545:
535:
534:
531:
529:Vapor pressure
525:
524:
523:12.7 g·L
521:
516:
513:
512:
509:
503:
502:
499:
493:
492:
489:
483:
482:
479:
475:
474:
471:
465:
464:
460:
456:
452:
448:
445:
440:
437:
436:
432:
431:
429:
428:
425:
417:
416:
415:
412:
411:
409:
408:
404:
401:
400:
398:
394:
391:
390:
382:
381:
380:
377:
376:
374:
373:
360:
358:
346:
343:
342:
339:
333:
332:
330:
329:
321:
319:
313:
312:
310:
309:
305:
303:
297:
296:
294:
293:
285:
283:
275:
272:
271:
261:
253:
252:
250:
249:
241:
239:
233:
232:
230:
229:
221:
219:
213:
212:
210:
209:
201:
199:
193:
192:
190:
189:
181:
179:
173:
172:
170:
169:
161:
159:
152:
149:
148:
146:
145:
137:
135:
130:
127:
126:
122:
121:
109:Trinitrophenol
100:
96:
95:
91:
90:
84:
83:
79:
78:
72:
71:
67:
66:
58:
57:
49:
48:
26:
24:
18:Trinitrophenol
14:
13:
10:
9:
6:
4:
3:
2:
2742:
2731:
2730:Organic acids
2728:
2726:
2723:
2721:
2718:
2717:
2715:
2706:
2703:
2701:
2700:0-471-18636-8
2697:
2693:
2689:
2685:
2681:
2677:
2673:
2668:
2664:
2659:
2658:
2654:
2645:
2641:
2637:
2633:
2629:
2625:
2621:
2614:
2611:
2605:
2603:
2599:
2586:
2582:
2576:
2573:
2560:
2556:
2552:
2546:
2543:
2531:
2527:
2520:
2517:
2504:
2500:
2494:
2491:
2487:
2484:
2479:
2476:
2463:
2459:
2455:
2448:
2445:
2441:
2437:
2434:
2429:
2426:
2415:on 2020-08-06
2414:
2410:
2404:
2401:
2396:
2392:
2388:
2384:
2380:
2376:
2369:
2366:
2361:
2357:
2352:
2347:
2343:
2339:
2335:
2328:
2325:
2312:
2308:
2304:
2303:"Picric Acid"
2297:
2294:
2289:
2283:
2279:
2275:
2268:
2265:
2261:
2257:
2256:
2251:
2244:
2238:
2235:
2224:
2220:
2213:
2210:
2205:
2203:9780470059357
2199:
2195:
2194:
2186:
2183:
2172:
2168:
2162:
2159:
2153:
2150:
2146:
2145:0-87013-426-4
2142:
2138:
2132:
2129:
2125:
2124:0-87013-426-4
2121:
2117:
2111:
2108:
2104:
2103:0-671-22784-X
2100:
2096:
2090:
2087:
2083:
2079:
2075:
2069:
2066:
2062:
2061:0-7509-1878-0
2058:
2054:
2048:
2045:
2041:
2040:The Great War
2035:
2032:
2028:
2027:
2022:
2017:
2014:
2002:
2001:
1996:
1990:
1987:
1982:
1978:
1974:
1972:0-7509-1878-0
1968:
1964:
1957:
1954:
1948:
1945:
1939:
1937:
1932:
1929:
1925:
1921:
1917:
1913:
1909:
1906:
1905:
1901:
1898:
1891:
1888:(in French).
1887:
1883:
1878:
1874:
1871:(in French).
1870:
1866:
1861:
1860:
1858:
1854:
1850:
1846:
1840:
1837:
1833:
1829:
1825:
1821:
1818:From p. 303:
1815:
1811:
1807:
1800:
1797:
1793:
1789:
1785:
1779:
1776:
1772:
1769:From p. 228:
1766:
1762:
1758:
1751:
1748:
1744:
1740:
1737:
1731:
1728:
1723:
1719:
1715:
1714:"Picric acid"
1709:
1706:
1701:
1697:
1690:
1688:
1686:
1684:
1680:
1675:
1669:
1665:
1661:
1657:
1654:. Cambridge:
1653:
1647:
1645:
1641:
1634:
1630:
1629:Styphnic acid
1627:
1625:
1622:
1620:
1617:
1615:
1612:
1609:
1606:
1605:
1601:
1599:
1597:
1593:
1589:
1585:
1581:
1579:
1578:Bomb disposal
1575:
1571:
1568:
1564:
1560:
1556:
1548:
1546:
1544:
1540:
1536:
1531:
1529:
1525:
1524:Western Front
1521:
1517:
1513:
1509:
1505:
1501:
1497:
1493:
1489:
1481:
1479:
1473:
1471:
1468:
1464:
1459:
1456:
1454:
1450:
1442:
1440:
1438:
1434:
1429:
1427:
1423:
1419:
1415:
1408:
1406:
1404:
1400:
1396:
1395:metallography
1392:
1384:
1382:
1379:
1377:
1373:
1369:
1365:
1361:
1353:
1351:
1345:
1341:
1337:
1333:
1329:
1325:
1321:
1320:sulfonic acid
1317:
1313:
1309:
1305:
1300:
1292:
1290:
1288:
1284:
1280:
1276:
1272:
1268:
1264:
1260:
1256:
1252:
1248:
1244:
1243:Thomas Edison
1236:
1232:
1229:
1225:
1221:
1217:
1213:
1209:
1205:
1201:
1197:
1193:
1189:
1185:
1180:
1177:
1173:
1169:
1165:
1161:
1157:
1148:
1144:
1142:
1138:
1134:
1130:
1126:
1122:
1118:
1117:
1112:
1108:
1104:
1103:
1098:
1094:
1090:
1086:
1082:
1078:
1077:EugĂšne Turpin
1074:
1070:
1066:
1062:
1058:
1053:
1051:
1047:
1043:
1039:
1035:
1031:
1027:
1022:
1016:
1011:
1007:
1003:
999:
995:
991:
987:
983:
975:
973:
971:
967:
963:
959:
956:
952:
944:
940:
936:
932:
912:
908:
896:
889:
884:
867:
861:
857:
855:
852:
851:
847:
845:
842:
841:
836:
832:
828:
824:
823:
819:
816:(Recommended)
815:
811:
810:
806:
803:(Permissible)
802:
798:
797:
793:
792:
787:
779:
775:
766:
765:
761:
757:
753:
751:
748:
747:
740:
733:
726:
702:
699:
698:
694:
693:
663:
660:
656:
655:
637:
634:
630:
629:
625:
620:
615:
611:
608:
604:
603:
599:
597:
592:
588:
583:
582:
578:
577:
572:
567:
563:
559:
555:
554:
550:
544:
540:
537:
536:
532:
530:
527:
526:
522:
519:
515:
514:
510:
508:
507:Boiling point
505:
504:
500:
498:
497:Melting point
495:
494:
490:
488:
485:
484:
480:
477:
476:
472:
470:
467:
466:
446:
443:
439:
438:
433:
424:
420:
413:
399:
389:
385:
378:
370:
366:
365:DTXSID4025909
362:
361:
359:
349:
345:
344:
340:
338:
335:
334:
327:
323:
322:
320:
318:
315:
314:
307:
306:
304:
302:
299:
298:
291:
287:
286:
284:
278:
274:
273:
269:
265:
262:
260:
258:ECHA InfoCard
255:
254:
247:
243:
242:
240:
238:
235:
234:
227:
223:
222:
220:
218:
215:
214:
207:
203:
202:
200:
198:
195:
194:
187:
183:
182:
180:
178:
175:
174:
167:
163:
162:
160:
156:
151:
150:
143:
139:
138:
136:
133:
129:
128:
123:
97:
89:
85:
77:
73:
68:
64:
59:
55:
50:
46:
41:
33:
19:
2725:Nitrophenols
2691:
2675:
2671:
2662:
2627:
2624:RSC Advances
2623:
2613:
2589:. Retrieved
2584:
2575:
2563:. Retrieved
2559:the original
2554:
2545:
2533:. Retrieved
2529:
2519:
2507:. Retrieved
2502:
2493:
2485:
2478:
2466:. Retrieved
2462:the original
2457:
2447:
2428:
2417:. Retrieved
2413:the original
2403:
2378:
2374:
2368:
2341:
2337:
2327:
2317:28 September
2315:. Retrieved
2311:the original
2306:
2296:
2273:
2267:
2253:
2246:
2242:
2237:
2226:. Retrieved
2222:
2212:
2192:
2185:
2174:. Retrieved
2170:
2161:
2152:
2136:
2131:
2115:
2110:
2094:
2089:
2073:
2068:
2052:
2047:
2039:
2038:Marc Ferro.
2034:
2024:
2016:
2005:. Retrieved
1999:
1989:
1962:
1956:
1947:
1935:
1919:
1915:
1900:
1889:
1885:
1872:
1868:
1856:
1839:
1831:
1827:
1823:
1819:
1813:
1809:
1799:
1791:
1790:, series 3,
1787:
1778:
1770:
1764:
1760:
1750:
1742:
1738:
1730:
1717:
1708:
1651:
1582:
1576:
1572:
1552:
1532:
1485:
1477:
1460:
1457:
1451:to test for
1446:
1430:
1412:
1388:
1380:
1357:
1343:
1296:
1287:pyrophyllite
1267:aniline dyes
1241:
1228:Dow Chemical
1212:gas lighting
1181:
1153:
1124:
1114:
1100:
1096:
1088:
1083:charges and
1054:
1006:Peter Woulfe
984:writings of
979:
950:
938:
934:
906:
905:
790:
759:
696:
595:
585:Main hazards
574:
542:
301:RTECS number
206:ChEMBL108541
125:Identifiers
99:Other names
38:Picric acid
2458:Tacomed.com
1543:olive green
1528:World War I
1520:trench foot
1443:Blood tests
1364:Explosive D
1360:ammunitions
1312:nitric acid
1216:Laclede Gas
1188:World War I
1168:World War I
1129:explosive D
907:Picric acid
760:Lethal dose
750:Flash point
579:(OHS/OSH):
478:Appearance
435:Properties
264:100.001.696
186:CHEBI:46149
101:Picric acid
2714:Categories
2503:hazard.com
2488:, Pg. 175.
2442:pdf, Pg.33
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2307:StainsFile
2228:2018-08-26
2176:2024-08-01
2063:pp.151â163
2007:2009-07-22
1911:explosive.
1892:: 113â142.
1875:: 531â543.
1857:suroxigéné
1816:: 301â305.
1767:: 204â232.
1635:References
1592:shipwrecks
1539:mole skins
1488:antiseptic
1482:Antiseptic
1453:creatinine
1426:hydrolysis
1391:metallurgy
1324:exothermic
1304:sulfonated
1247:phonograph
1073:detonation
982:alchemical
970:antiseptic
931:IUPAC name
607:Pictograms
589:explosive
469:Molar mass
326:A49OS0F91S
217:ChemSpider
153:3D model (
132:CAS Number
2684:0043-0374
1619:RE factor
1584:Munitions
1535:fly tyers
1422:histology
1409:Histology
1399:austenite
1293:Synthesis
1061:artillery
1034:explosive
990:nitrating
966:explosive
854:RE factor
598:labelling
337:UN number
308:TJ7875000
2509:13 April
2436:Archived
2360:25023614
1997:(1901).
1981:40348081
1724:(NIOSH).
1702:(NIOSH).
1602:See also
1596:seawater
1588:warships
1559:friction
1504:smallpox
1474:Skin dye
1437:collagen
1418:fixative
1368:ammonium
1224:Monsanto
1192:reported
1137:picrates
1116:Ecrasite
1089:Melinite
1081:blasting
1046:military
962:nitrated
929:OH. Its
833:75 mg/m
697:NFPA 704
569:Hazards
560:(χ)
237:DrugBank
117:Melinite
2676:XXXVIII
2632:Bibcode
2591:22 July
2565:22 July
2535:20 July
2482:(1922)
2468:13 June
1696:"#0515"
1567:picrate
1537:to dye
1526:during
1496:malaria
1463:glucose
1328:aspirin
1283:shellac
1255:benzene
1220:toluene
1200:aspirin
1176:Toluene
1125:Dunnite
1097:Lyddite
976:History
958:phenols
888:what is
886: (
539:Acidity
487:Density
463:
341:UN1344
277:PubChem
246:DB03651
142:88-89-1
119:Lyddite
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1502:, and
1500:herpes
1299:phenol
1285:, and
1275:xylene
1261:, and
1184:phenol
1166:, and
1162:, the
1158:, the
1030:phenol
998:indigo
955:acidic
951:pikros
947:ÏÎčÎșÏÏÏ
909:is an
883:verify
880:
419:SMILES
197:ChEMBL
70:Names
32:Lydite
2530:Stuff
2395:91593
2147:p. 97
2105:p. 24
2084:p. 64
1563:water
1555:shock
1508:gauze
1492:burns
1316:nitro
1306:with
1109:with
1038:salts
1002:resin
943:Greek
858:1.20
791:NIOSH
551:0.38
384:InChI
177:ChEBI
155:JSmol
2696:ISBN
2680:ISSN
2593:2011
2567:2011
2537:2021
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2470:2017
2391:PMID
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2319:2012
2282:ISBN
2252:In:
2198:ISBN
2141:ISBN
2120:ISBN
2099:ISBN
2078:ISBN
2057:ISBN
1977:OCLC
1967:ISBN
1847:and
1830:amer
1824:amer
1668:ISBN
1557:and
1376:TATB
1354:Uses
1226:and
1208:coke
1204:coal
1133:fuze
1093:Lydd
1067:and
994:silk
827:IDLH
689:P501
681:P280
677:P233
673:P230
669:P212
665:P210
651:H331
647:H311
643:H302
639:H206
317:UNII
290:6954
226:6688
2640:doi
2383:doi
2346:doi
1938:...
1924:doi
1660:doi
1389:In
1372:TNT
1344:Pca
1330:or
1257:at
1127:or
1119:in
939:TNP
933:is
814:REL
801:PEL
596:GHS
353:EPA
280:CID
115:TNP
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