48:
339:
226:
896:
35:
528:
523:
758:
653:
57:
882:
927:
of the carbonyl carbon resulting in increased delocalization in the molecule. This stability would be lost by addition of a reagent to the carbonyl group. Hence, these compounds are more resistant to addition reactions. Also, with carboxylic acids, there is the effect of the compound acting as a
936:
Dry DNPH is friction and shock sensitive. For this reason, it’s supplied damp or ‘wetted’ when a school purchases it from a chemical supplier. If DNPH is stored improperly and left to dry out, it can become explosive. It is an artificial uncoupler of the electron transport chain (ETC).
907:
DNP-derived hydrazones have characteristic melting points, facilitating identification of the carbonyl. In particular, the use of DNPH was developed by Brady and Elsmie. Modern spectroscopic and spectrometric techniques have superseded these techniques.
536:
503:
1050:
Tameem, Abdassalam
Abdelhafiz; Salhin, Abdussalam; Saad, Bahruddin; Rahman, Ismail Ab.; Saleh, Muhammad Idiris; Ng, Shea-Lin; Fun, Hoong-Kun (2006). "Benzophenone 2,4-dinitrophenylhydrazone".
606:
666:
1140:
143:
388:
1444:
578:
1183:
1439:
1021:
353:
1418:
602:
484:
1077:
Brady, Oscar L.; Elsmie, Gladys V. (1926). "The use of 2:4-dinitrophenylhydrazine as a reagent for aldehydes and ketones".
865:
598:
673:
770:
572:
296:
317:
47:
527:
928:
base, leaving the resulting carboxylate negatively charged and hence no longer vulnerable to nucleophilic attack.
1348:
1203:
233:
1176:
749:
586:
614:
522:
1213:
221:
183:
1408:
861:
550:
515:
1010:
1413:
1383:
1088:
951:
75:
1449:
1333:
1169:
946:
923:, for which there is resonance-associated stability as a lone-pair of electrons interacts with the
594:
334:
109:
895:
582:
1079:
1017:
1008:
Mohrig, Jerry R.; Hammond, Christina Noring; Morrill, Terence C.; Neckers, Douglas C. (1998).
981:
745:
725:
629:
203:
1363:
1096:
1059:
990:
912:
697:
618:
467:
411:
864:
as two molecules joining together with loss of water. Mechanistically, it is an example of
808:
carbonyls give more yellow color. The reaction between DNPH and a generic ketone to form a
732:. For this reason DNPH is usually handled as a wet powder. DNPH is a precursor to the drug
305:
34:
1368:
1278:
119:
1092:
757:
635:
338:
225:
163:
1248:
644:
17:
1433:
1403:
1398:
1328:
1313:
1258:
1208:
790:
786:
456:
214:
622:
285:
1388:
1373:
1358:
886:
590:
1114:
1303:
1283:
1268:
1233:
976:
956:
900:
804:
of the dinitrophenylhydrazone. Aromatic carbonyls give red precipitates whereas
801:
903:
is added to a solution of 2,4-DNPH and heated, an orange-red precipitate forms.
1378:
1353:
1323:
1308:
1273:
1253:
1192:
1063:
1012:
Experimental
Organic Chemistry: A Balanced Approach, Macroscale and Microscale
438:
194:
994:
911:
DNPH does not react with other carbonyl-containing functional groups such as
564:
1393:
1343:
1338:
1318:
1298:
1293:
1288:
1243:
1238:
1223:
924:
809:
805:
721:
800:. A positive test is signalled by the formation of a yellow, orange or red
1115:"What is 2,4-DNPH and Why Are Schools Carrying Out Controlled Explosions?"
1228:
1100:
797:
782:
733:
729:
1218:
272:
234:
920:
793:
174:
643:
Except where otherwise noted, data are given for materials in their
560:
872:
group to the C=O carbonyl group, followed by the elimination of a H
260:
56:
1141:"Bomb disposal squads detonate chemical stocks in British schools"
916:
894:
881:
880:
154:
142:
132:
362:
InChI=1S/C6H6N4O4/c7-8-5-2-1-4(9(11)12)3-6(5)10(13)14/h1-3,8H,7H2
889:. Selected parameters: C=N, 128 pm; N-N, 1.38 pm, N-N-C(Ar), 119
461:
198 to 202 °C (388 to 396 °F; 471 to 475 K) dec.
372:
InChI=1/C6H6N4O4/c7-8-5-2-1-4(9(11)12)3-6(5)10(13)14/h1-3,8H,7H2
251:
1165:
556:
1161:
610:
322:
55:
46:
781:, is prepared by dissolving DNPH in a solution containing
661:
720:. DNPH is a red to orange solid. It is a substituted
1016:. New York: W.H. Freeman and Company. p. 530.
769:DNPH is a reagent in instructional laboratories on
1009:
1040:, 4th Edition, 2000, Graham Hill and John Holman
284:
118:
1177:
8:
885:X-ray structure of DNP-derived hydrazone of
1184:
1170:
1162:
337:
224:
202:
26:
304:
967:
724:. The solid is relatively sensitive to
393:
358:
333:
744:It can be prepared by the reaction of
215:
365:Key: HORQAOAYAYGIBM-UHFFFAOYSA-N
182:
162:
7:
375:Key: HORQAOAYAYGIBM-UHFFFAOYAM
275:
259:
868:: nucleophilic addition of the -NH
25:
498:Flammable, possibly carcinogenic
1052:Acta Crystallographica Section E
756:
651:
526:
521:
33:
647:(at 25 °C , 100 kPa).
1445:Reagents for organic chemistry
485:Occupational safety and health
1:
866:addition-elimination reaction
860:This reaction is, overall, a
977:"2,4-Dinitrophenylhydrazine"
789:. This solution is used to
771:qualitative organic analysis
80:(2,4-Dinitrophenyl)hydrazine
42:
28:2,4-Dinitrophenylhydrazine
1466:
852:NHN=CRR' + H
686:2,4-Dinitrophenylhydrazine
443:198.14 g/mol
1199:
1064:10.1107/S1600536806048112
641:
502:
482:
477:
404:
384:
349:
102:
86:
74:
69:
41:
32:
1440:Nitrobenzene derivatives
995:10.15227/orgsyn.013.0036
975:Allen, C. F. H. (1933).
816:RR'C=O + C
750:2,4-dinitrochlorobenzene
573:Precautionary statements
904:
890:
785:and some concentrated
396:c1cc(c(cc1(=O))(=O))NN
60:
51:
18:Dinitrophenylhydrazine
898:
884:
862:condensation reaction
451:Red or orange powder
59:
50:
1414:Tetrafluorohydrazine
1384:Pivalylbenzhydrazine
1101:10.1039/AN9265100077
1038:Chemistry in Context
76:Preferred IUPAC name
1093:1926Ana....51...77B
1058:(12): o5686–o5688.
468:Solubility in water
29:
905:
891:
674:Infobox references
61:
52:
27:
1427:
1426:
1147:. 2 November 2016
1121:. 7 November 2016
1119:Compound Interest
982:Organic Syntheses
952:Fehling's reagent
836: → C
746:hydrazine sulfate
682:Chemical compound
680:
679:
630:Safety data sheet
551:Hazard statements
318:CompTox Dashboard
144:Interactive image
65:
64:
16:(Redirected from
1457:
1364:Phenoxypropazine
1186:
1179:
1172:
1163:
1157:
1156:
1154:
1152:
1137:
1131:
1130:
1128:
1126:
1111:
1105:
1104:
1074:
1068:
1067:
1047:
1041:
1034:
1028:
1027:
1015:
1005:
999:
997:
972:
947:Tollens' reagent
913:carboxylic acids
812:is shown below:
779:Borche's reagent
760:
698:organic compound
664:
658:
655:
654:
624:
620:
616:
612:
608:
604:
600:
596:
592:
588:
584:
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566:
562:
558:
530:
525:
412:Chemical formula
342:
341:
326:
324:
308:
288:
277:
263:
236:
228:
217:
206:
186:
166:
146:
122:
97:Borche's reagent
43:
37:
30:
21:
1465:
1464:
1460:
1459:
1458:
1456:
1455:
1454:
1430:
1429:
1428:
1423:
1369:Phenylhydrazine
1195:
1190:
1160:
1150:
1148:
1139:
1138:
1134:
1124:
1122:
1113:
1112:
1108:
1076:
1075:
1071:
1049:
1048:
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1035:
1031:
1024:
1007:
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1002:
974:
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965:
943:
934:
875:
871:
855:
851:
847:
843:
839:
835:
831:
827:
823:
819:
775:Brady's reagent
767:
742:
719:
715:
711:
707:
703:
683:
676:
671:
670:
669: ?)
660:
656:
652:
648:
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553:
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311:
291:
278:
266:
246:
209:
189:
169:
149:
136:
125:
112:
98:
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95:Brady's reagent
94:
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90:
82:
81:
23:
22:
15:
12:
11:
5:
1463:
1461:
1453:
1452:
1447:
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1432:
1431:
1425:
1424:
1422:
1421:
1416:
1411:
1406:
1401:
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1391:
1386:
1381:
1376:
1371:
1366:
1361:
1356:
1351:
1346:
1341:
1336:
1331:
1326:
1321:
1316:
1311:
1306:
1301:
1296:
1291:
1286:
1281:
1276:
1271:
1266:
1261:
1256:
1251:
1249:Carbohydrazide
1246:
1241:
1236:
1231:
1226:
1221:
1216:
1211:
1206:
1200:
1197:
1196:
1191:
1189:
1188:
1181:
1174:
1166:
1159:
1158:
1132:
1106:
1087:(599): 77–78.
1069:
1042:
1029:
1022:
1000:
966:
964:
961:
960:
959:
954:
949:
942:
939:
933:
930:
893:
892:
873:
869:
858:
857:
853:
849:
845:
841:
837:
833:
829:
825:
821:
817:
766:
763:
762:
761:
741:
738:
717:
713:
709:
705:
701:
681:
678:
677:
672:
650:
649:
645:standard state
642:
639:
638:
633:
626:
625:
607:P305+P351+P338
576:
571:
568:
567:
554:
549:
546:
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108:
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83:
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78:
72:
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66:
63:
62:
53:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1462:
1451:
1448:
1446:
1443:
1441:
1438:
1437:
1435:
1420:
1417:
1415:
1412:
1410:
1407:
1405:
1404:Semicarbazone
1402:
1400:
1399:Semicarbazide
1397:
1395:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1355:
1352:
1350:
1347:
1345:
1342:
1340:
1337:
1335:
1332:
1330:
1329:Metfendrazine
1327:
1325:
1322:
1320:
1317:
1315:
1314:Isocarboxazid
1312:
1310:
1307:
1305:
1302:
1300:
1297:
1295:
1292:
1290:
1287:
1285:
1282:
1280:
1277:
1275:
1272:
1270:
1267:
1265:
1262:
1260:
1259:Dihydralazine
1257:
1255:
1252:
1250:
1247:
1245:
1242:
1240:
1237:
1235:
1232:
1230:
1227:
1225:
1222:
1220:
1217:
1215:
1212:
1210:
1209:Acylhydrazine
1207:
1205:
1202:
1201:
1198:
1194:
1187:
1182:
1180:
1175:
1173:
1168:
1167:
1164:
1146:
1142:
1136:
1133:
1120:
1116:
1110:
1107:
1102:
1098:
1094:
1090:
1086:
1082:
1081:
1073:
1070:
1065:
1061:
1057:
1053:
1046:
1043:
1039:
1036:Adapted from
1033:
1030:
1025:
1023:0-7167-2818-4
1019:
1014:
1013:
1004:
1001:
996:
992:
988:
984:
983:
978:
971:
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962:
958:
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953:
950:
948:
945:
944:
940:
938:
931:
929:
926:
922:
918:
914:
909:
902:
897:
888:
883:
879:
878:
877:
867:
863:
815:
814:
813:
811:
807:
803:
799:
795:
792:
788:
787:sulfuric acid
784:
780:
776:
772:
764:
759:
755:
754:
753:
751:
747:
739:
737:
735:
731:
727:
723:
699:
695:
691:
687:
675:
668:
663:
646:
640:
637:
634:
631:
628:
627:
577:
574:
570:
569:
555:
552:
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544:
541:
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534:
533:
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520:
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512:
508:
506:
501:
497:
492:
491:
487:
486:
481:
476:
472:
469:
465:
464:
460:
458:
457:Melting point
455:
454:
450:
447:
446:
442:
440:
437:
436:
416:
413:
409:
408:
403:
394:
390:
383:
369:
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348:
340:
336:
335:DTXSID2059485
332:
331:
329:
319:
315:
314:
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241:
239:
237:
232:
231:
227:
223:
220:
218:
216:ECHA InfoCard
213:
212:
205:
201:
200:
198:
196:
193:
192:
185:
181:
180:
178:
176:
173:
172:
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156:
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145:
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134:
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117:
116:
114:
111:
107:
106:
101:
85:
77:
73:
68:
58:
54:
49:
45:
44:
40:
36:
31:
19:
1389:Procarbazine
1374:Pildralazine
1359:Pheniprazine
1263:
1149:. Retrieved
1145:The Guardian
1144:
1135:
1123:. Retrieved
1118:
1109:
1084:
1078:
1072:
1055:
1051:
1045:
1037:
1032:
1011:
1003:
986:
980:
970:
935:
910:
906:
887:benzophenone
876:O molecule:
859:
778:
774:
768:
743:
693:
689:
685:
684:
542:
504:
494:Main hazards
483:
184:ChEMBL352799
103:Identifiers
87:Other names
1304:Iproclozide
1284:Hydralazine
1269:Endralazine
1234:Cadralazine
957:Schiff test
901:3-heptanone
802:precipitate
537:Signal word
488:(OHS/OSH):
448:Appearance
405:Properties
222:100.003.918
164:CHEBI:66932
1450:Hydrazines
1434:Categories
1379:Pimagedine
1354:Phenelzine
1324:Mebanazine
1309:Iproniazid
1274:Gyromitrin
1254:Daminozide
1193:Hydrazines
1125:26 October
963:References
516:Pictograms
439:Molar mass
306:1N39KD7QPJ
195:ChemSpider
131:3D model (
110:CAS Number
1394:Safrazine
1344:Octamoxin
1339:Nialamide
1319:Isoniazid
1299:Hydrazone
1294:Hydrazine
1289:Hydrazide
1244:Carbidopa
1239:Carbazide
1224:Agaritine
925:p orbital
810:hydrazone
806:aliphatic
798:aldehydes
740:Synthesis
722:hydrazine
696:) is the
619:P370+P378
615:P337+P313
603:P301+P312
507:labelling
243:204-309-3
235:EC Number
1229:Benmoxin
1151:19 March
941:See also
783:methanol
765:DNP test
734:Sivifene
730:friction
690:2,4-DNPH
478:Hazards
120:119-26-6
89:2,4-DNPH
1219:Adjudin
1089:Bibcode
1080:Analyst
794:ketones
667:what is
665: (
543:Warning
473:Slight
433:
286:3772977
273:PubChem
204:3001507
91:2,4-DNP
1204:4-PTSC
1020:
989:: 36.
932:Safety
921:esters
919:, and
917:amides
791:detect
662:verify
659:
632:(SDS)
389:SMILES
261:C11283
175:ChEMBL
70:Names
899:When
748:with
726:shock
354:InChI
155:ChEBI
133:JSmol
1419:UDMH
1409:SDMH
1264:DNPH
1153:2018
1127:2022
1018:ISBN
832:NHNH
796:and
728:and
716:NHNH
694:DNPH
636:MSDS
623:P501
611:P330
599:P280
595:P270
591:P264
587:P241
583:P240
579:P210
565:H319
561:H302
557:H228
297:UNII
252:KEGG
93:DNPH
1349:PEH
1334:MMH
1279:HBT
1214:ADH
1097:doi
1060:doi
991:doi
844:(NO
824:(NO
777:or
708:(NO
692:or
505:GHS
323:EPA
276:CID
1436::
1143:.
1117:.
1095:.
1085:51
1083:.
1056:62
1054:.
987:13
985:.
979:.
915:,
773:.
752::
736:.
621:,
617:,
613:,
609:,
605:,
601:,
597:,
593:,
589:,
585:,
581:,
563:,
559:,
509::
1185:e
1178:t
1171:v
1155:.
1129:.
1103:.
1099::
1091::
1066:.
1062::
1026:.
998:.
993::
874:2
870:2
856:O
854:2
850:2
848:)
846:2
842:3
840:H
838:6
834:2
830:2
828:)
826:2
822:3
820:H
818:6
718:2
714:2
712:)
710:2
706:3
704:H
702:6
700:C
688:(
657:N
431:4
429:O
427:4
425:N
423:6
421:H
419:6
417:C
325:)
321:(
135:)
20:)
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