429:
417:
77:
462:
336:
477:
390:
447:
20:
750:
Algar, W. Russ; Prasuhn, Duane E.; Stewart, Michael H.; Jennings, Travis L.; Blanco-Canosa, Juan B.; Dawson, Philip E.; Medintz, Igor L. (2011). "The
Controlled Display of Biomolecules on Nanoparticles: A Challenge Suited to Bioorthogonal Chemistry".
368:-dialkylhydrazones the C=N bond can be hydrolysed, oxidised and reduced, the N–N bond can be reduced to the free amine. The carbon atom of the C=N bond can react with organometallic nucleophiles. The alpha-hydrogen atom is more acidic by 10
401:
Several methods are known to recover carbonyl compounds from N,N-dialkylhydrazones. Procedures include oxidative, hydrolytic or reductive cleavage conditions and can be compatible with a wide range of functional groups.
476:
1226:
Tameem, Abdassalam
Abdelhafiz; Salhin, Abdussalam; Saad, Bahruddin; Rahman, Ismail Ab.; Saleh, Muhammad Idiris; Ng, Shea-Lin; Fun, Hoong-Kun (2006). "Benzophenone 2,4-dinitrophenylhydrazone".
938:
Outirite, Moha; Lebrini, Mounim; Lagrenée, Michel; Bentiss, Fouad (2008). "New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating".
178:), e.g. antibodies against a certain type of cancer cell. The hydrazone-based bond is stable at neutral pH (in the blood), but is rapidly destroyed in the acidic environment of
137:
512:
428:
355:
416:
1271:
1086:
Enders, Dieter; Reinhold, Ulrich (1997). "Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond".
2190:
434:
1051:
Lazny, R.; Nodzewska, A. (2010). "N,N-dialkylhydrazones in organic synthesis. From simple N,N-dimethylhydrazones to supported chiral auxiliaries".
2195:
126:
2230:
461:
446:
940:
546:
2465:
1264:
174:
strategies. Hydrazone-based coupling methods are used in medical biotechnology to couple drugs to targeted antibodies (see
2094:
76:
303:
295:
1006:
Wang, H; Dai, X.-J.; Li, C.-J. (2017). "Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds".
389:
280:
786:
Wu, Anna M.; Senter, Peter D. (7 September 2005). "Arming antibodies: prospects and challenges for immunoconjugates".
1156:
Enders, Dieter; Kipphardt, Helmut; Fey, Peter (1987). "Asymmetric
Syntheses Using the SAMP-/RAMP-Hydrazone Method: (
2491:
2310:
1667:
1257:
2395:
2250:
327:
160:
2223:
1704:
373:
71:
Hydrazine, organohydrazines, and 1,1-diorganohydrazines react with aldehydes and ketones to give hydrazones.
2260:
2177:
175:
2077:
977:
234:
148:
111:
2455:
2184:
2072:
152:
2460:
2430:
2153:
1598:
287:
2486:
2380:
2216:
1459:
1138:
1033:
811:
369:
330:, hydrazones can serve as organometallic reagent surrogates to react with various electrophiles.
2143:
2113:
1871:
1493:
1208:
1068:
1025:
880:
860:
803:
768:
732:
612:
579:
552:
542:
536:
335:
323:
164:
2410:
1848:
1342:
1280:
1235:
1200:
1169:
1130:
1095:
1060:
1017:
1008:
986:
949:
889:
850:
842:
795:
760:
722:
714:
683:
652:
381:
291:
56:
31:
2415:
2325:
2067:
1826:
1821:
1804:
1787:
1588:
1337:
83:
372:
compared to the ketone and therefore more nucleophilic. Deprotonation with for instance
2295:
2138:
2133:
2009:
2004:
1999:
1792:
1759:
1543:
1525:
1515:
855:
830:
727:
702:
307:
171:
99:
87:
1099:
2480:
2450:
2445:
2375:
2360:
2305:
2255:
2158:
2106:
2037:
1923:
1913:
1908:
1898:
1893:
1843:
1838:
1754:
1749:
1739:
1593:
1548:
1510:
1498:
1469:
1347:
1142:
467:
182:
of the cell. The drug is thereby released in the cell, where it exerts its function.
110:
Hydrazones are the basis for various analyses of ketones and aldehydes. For example,
1037:
908:
815:
2435:
2420:
2405:
2089:
1976:
1971:
1948:
1699:
1538:
1464:
1401:
1396:
1374:
1330:
1315:
1305:
497:
483:
95:
380:
which can be alkylated by alkyl halides. The hydrazines SAMP and RAMP function as
2350:
2330:
2315:
2280:
2148:
2101:
2062:
1943:
1831:
1816:
1811:
1799:
1364:
1359:
1325:
1320:
1310:
1288:
1121:)-(+)-1-amino-2-methoxymethylpyrrolidine (RAMP), Versatile Chiral Auxiliaries".
718:
607:
570:
532:
507:
299:
130:
2425:
2400:
2370:
2355:
2320:
2300:
2239:
2057:
2048:
1928:
1883:
1779:
1744:
1734:
1674:
1610:
1533:
1481:
1239:
687:
452:
122:
1188:
1173:
1134:
917:-pyrazole from hydrazones and/or ketones monitored by high resolution ESI-MS"
893:
656:
556:
538:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
2440:
2390:
2385:
2365:
2340:
2335:
2290:
2285:
2270:
2024:
1938:
1903:
1888:
1876:
1719:
1503:
953:
145:
60:
1212:
1072:
1029:
973:-pyrazoles from chalcones and hydrazine under mechanochemical ball milling"
864:
846:
807:
772:
736:
226:
hydrazones are 10- to 10-fold more sensitive to hydrolysis than analogous
19:
2275:
2032:
1986:
1953:
1649:
1555:
1429:
1384:
1369:
991:
968:
319:
238:
179:
46:
2265:
1994:
1918:
1769:
1764:
1729:
1714:
1709:
1679:
1662:
1486:
1413:
1379:
1021:
310:
or β-keto-esters and aryl diazonium salts. Hydrazones are converted to
118:
91:
1204:
1064:
764:
233:
When derived from hydrazine itself, hydrazones condense with a second
2082:
2014:
1858:
1567:
1560:
1454:
1435:
1424:
1408:
1354:
227:
156:
115:
42:
1249:
799:
671:
640:
1963:
1933:
1866:
1724:
1689:
1684:
1657:
1605:
1572:
1476:
1300:
703:"Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis"
502:
486:. Selected parameters: C=N, 128 pm; N-N, 138 pm, N-N-C(Ar), 119 pm
311:
242:
223:
1391:
2212:
1253:
2208:
967:
Zhang, Ze; Tan, Ya-Jun; Wang, Chun-Shan; Wu, Hao-Hao (2014).
1189:"Recovery of Carbonyl Compounds from N,N-Dialkylhydrazones"
125:
cartridge. The hydrazones are then eluted and analyzed by
397:
Recovery of carbonyl compounds from N,N-dialkylhydrazones
1113:
Enders, Dieter; Fey, Peter; Kipphardt, Helmut (1987). "(
878:
Day, A. C.; Whiting, M. C. (1970). "Acetone
Hydrazone".
641:"Schmelzpunkt des Phenylhydrazins und einiger Osazone"
1187:
Enders, Dieter; Wortmann, Lars; Peters, René (2000).
1117:)-(−)-1-Amino-2-methoxymethylpyrrolidine (SAMP) and (
672:"Ueber einige Osazone und Hydrazone der Zuckergruppe"
302:
compounds. Hydrazones can also be synthesized by the
2126:
2046:
2023:
1985:
1962:
1857:
1778:
1648:
1625:
1581:
1524:
1447:
1422:
1287:
314:
when used in the preparation of 3,5-disubstituted 1
913:-catalyzed synthesis of azines and 3,5-diphenyl-1
422:Benzophenone hydrazone, an illustrative hydrazone
575:Metalloenamines: 1-butyl-10-methyl-Δ-2-octalone"
831:"Hydrolytic stability of hydrazones and oximes"
676:Berichte der Deutschen Chemischen Gesellschaft
645:Berichte der Deutschen Chemischen Gesellschaft
356:Enders SAMP/RAMP hydrazone alkylation reaction
49:by the replacement of the oxygen =O with the =
2224:
1265:
513:Hydrogenation of carbon–nitrogen double bonds
455:(acetaldehyde methylformylhydrazone), a toxin
8:
482:X-ray structure of DNP-derived hydrazone of
571:"Monoalkylation of α,β-Unsaturated Ketones
59:. They are formed usually by the action of
23:Structure of the hydrazone functional group
2231:
2217:
2209:
1645:
1444:
1272:
1258:
1250:
701:Kölmel, Dominik K.; Kool, Eric T. (2017).
190:Hydrazones are susceptible to hydrolysis:
990:
854:
726:
271:
267:
263:
259:
255:
251:
216:
212:
208:
204:
200:
196:
94:, which was developed by German chemist
52:
37:
18:
524:
409:
921:Indian Journal of Chemistry, Section B
127:high-performance liquid chromatography
907:Lasri, Jamal; Ismail, Ali I. (2018).
7:
969:"One-pot synthesis of 3,5-diphenyl-1
279:Hydrazones are intermediates in the
606:Day, A. C.; Whiting, M. C. (1970).
322:, a reaction also well known using
14:
941:Journal of Heterocyclic Chemistry
829:Kalia, J.; Raines, R. T. (2008).
144:(abbreviated as FCCP) is used to
1228:Acta Crystallographica Section E
475:
460:
445:
427:
415:
388:
334:
142:-trifluoromethoxyphenylhydrazone
75:
569:Stork, G.; Benaim, J. (1977).
16:Organic compounds - Hydrazones
1:
1193:Accounts of Chemical Research
1160:)-(+)-4-methyl-3-heptanone".
1100:10.1016/S0957-4166(97)00208-5
286:Hydrazones are reactants in
170:Hydrazones are the basis of
90:to form hydrazones known as
719:10.1021/acs.chemrev.7b00090
98:as a test to differentiate
2508:
594:, vol. 6, p. 242
470:, an antihypertensive drug
353:
2246:
2167:
1240:10.1107/S1600536806048112
688:10.1002/cber.189402702249
627:, vol. 6, p. 10
328:transition metal catalyst
161:oxidative phosphorylation
63:on ketones or aldehydes.
1174:10.15227/orgsyn.065.0183
1135:10.15227/orgsyn.065.0173
894:10.15227/orgsyn.050.0003
657:10.1002/cber.19080410120
374:lithium diisopropylamide
304:Japp–Klingemann reaction
296:Bamford–Stevens reaction
2178:chemical classification
954:10.1002/jhet.5570450231
439:-chlorophenyl hydrazone
281:Wolff–Kishner reduction
1088:Tetrahedron: Asymmetry
847:10.1002/anie.200802651
753:Bioconjugate Chemistry
670:Fischer, Emil (1894).
639:Fischer, Emil (1908).
112:dinitrophenylhydrazine
41:. They are related to
24:
2185:chemical nomenclature
22:
2461:Tetrafluorohydrazine
2431:Pivalylbenzhydrazine
992:10.3987/COM-13-12867
909:"Metal-free and FeCl
835:Angew. Chem. Int. Ed
788:Nature Biotechnology
288:hydrazone iodination
1641:not C, H or O)
1234:(12): o5686–o5688.
713:(15): 10358–10376.
608:"Acetone hydrazone"
541:, New York: Wiley,
370:orders of magnitude
121:is the basis of an
34:with the structure
2083:Hypervalent iodine
1022:10.1038/nchem.2677
350:-dialkylhydrazones
25:
2492:Functional groups
2474:
2473:
2206:
2205:
2144:Sulfenyl chloride
2122:
2121:
1621:
1620:
1440:(only C, H and O)
1281:Functional groups
1205:10.1021/ar990062y
1162:Organic Syntheses
1123:Organic Syntheses
1094:(12): 1895–1946.
1065:10.1021/cr900067y
881:Organic Syntheses
765:10.1021/bc200065z
625:Collected Volumes
613:Organic Syntheses
592:Collected Volumes
580:Organic Syntheses
435:Carbonyl cyanide
324:hydrazine hydrate
165:molecular biology
138:carbonyl cyanide-
32:organic compounds
2499:
2411:Phenoxypropazine
2233:
2226:
2219:
2210:
2173:
2078:Trifluoromethoxy
1646:
1642:
1445:
1441:
1294:
1274:
1267:
1260:
1251:
1244:
1243:
1223:
1217:
1216:
1184:
1178:
1177:
1153:
1147:
1146:
1110:
1104:
1103:
1083:
1077:
1076:
1059:(3): 1386–1434.
1053:Chemical Reviews
1048:
1042:
1041:
1009:Nature Chemistry
1003:
997:
996:
994:
964:
958:
957:
935:
929:
928:
904:
898:
896:
875:
869:
868:
858:
826:
820:
819:
783:
777:
776:
747:
741:
740:
730:
707:Chemical Reviews
698:
692:
691:
682:(2): 2486–2492.
667:
661:
660:
636:
630:
628:
621:
603:
597:
595:
588:
566:
560:
559:
529:
479:
464:
449:
431:
419:
392:
382:chiral auxiliary
338:
292:Shapiro reaction
275:
219:
79:
57:functional group
55:
40:
2507:
2506:
2502:
2501:
2500:
2498:
2497:
2496:
2477:
2476:
2475:
2470:
2416:Phenylhydrazine
2242:
2237:
2207:
2202:
2171:
2163:
2118:
2073:Trichloromethyl
2068:Trifluoromethyl
2042:
2019:
1981:
1958:
1853:
1822:Phosphine oxide
1774:
1640:
1638:
1637:
1635:
1633:
1631:
1629:
1627:
1617:
1577:
1520:
1439:
1438:
1433:
1428:
1418:
1292:
1291:
1283:
1278:
1248:
1247:
1225:
1224:
1220:
1186:
1185:
1181:
1155:
1154:
1150:
1112:
1111:
1107:
1085:
1084:
1080:
1050:
1049:
1045:
1005:
1004:
1000:
966:
965:
961:
937:
936:
932:
912:
906:
905:
901:
877:
876:
872:
828:
827:
823:
800:10.1038/nbt1141
785:
784:
780:
749:
748:
744:
700:
699:
695:
669:
668:
664:
638:
637:
633:
623:
605:
604:
600:
590:
568:
567:
563:
549:
531:
530:
526:
521:
494:
487:
480:
471:
465:
456:
450:
441:
432:
423:
420:
408:
399:
376:(LDA) gives an
358:
352:
273:
269:
265:
261:
257:
253:
249:
218:
214:
210:
206:
202:
198:
194:
188:
129:(HPLC) using a
108:
100:monosaccharides
88:reducing sugars
84:Phenylhydrazine
69:
54:
50:
39:
35:
30:are a class of
17:
12:
11:
5:
2505:
2503:
2495:
2494:
2489:
2479:
2478:
2472:
2471:
2469:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2413:
2408:
2403:
2398:
2393:
2388:
2383:
2378:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2328:
2323:
2318:
2313:
2308:
2303:
2298:
2296:Carbohydrazide
2293:
2288:
2283:
2278:
2273:
2268:
2263:
2258:
2253:
2247:
2244:
2243:
2238:
2236:
2235:
2228:
2221:
2213:
2204:
2203:
2201:
2200:
2199:
2198:
2193:
2181:
2174:
2168:
2165:
2164:
2162:
2161:
2159:Sulfinylamines
2156:
2151:
2146:
2141:
2139:Phosphoramides
2136:
2134:Isothiocyanate
2130:
2128:
2124:
2123:
2120:
2119:
2117:
2116:
2111:
2110:
2109:
2099:
2098:
2097:
2087:
2086:
2085:
2080:
2075:
2070:
2065:
2054:
2052:
2044:
2043:
2041:
2040:
2035:
2029:
2027:
2021:
2020:
2018:
2017:
2012:
2010:Selenenic acid
2007:
2005:Seleninic acid
2002:
2000:Selenonic acid
1997:
1991:
1989:
1983:
1982:
1980:
1979:
1974:
1968:
1966:
1960:
1959:
1957:
1956:
1951:
1946:
1941:
1936:
1931:
1926:
1921:
1916:
1911:
1906:
1901:
1896:
1891:
1886:
1881:
1880:
1879:
1869:
1863:
1861:
1855:
1854:
1852:
1851:
1846:
1841:
1836:
1835:
1834:
1824:
1819:
1814:
1809:
1808:
1807:
1797:
1796:
1795:
1793:Phosphodiester
1784:
1782:
1776:
1775:
1773:
1772:
1767:
1762:
1757:
1752:
1747:
1742:
1737:
1732:
1727:
1722:
1717:
1712:
1707:
1702:
1697:
1692:
1687:
1682:
1677:
1672:
1671:
1670:
1665:
1654:
1652:
1643:
1639:(one element,
1623:
1622:
1619:
1618:
1616:
1615:
1614:
1613:
1603:
1602:
1601:
1596:
1585:
1583:
1579:
1578:
1576:
1575:
1570:
1565:
1564:
1563:
1553:
1552:
1551:
1546:
1541:
1530:
1528:
1522:
1521:
1519:
1518:
1516:Methylenedioxy
1513:
1508:
1507:
1506:
1501:
1491:
1490:
1489:
1484:
1474:
1473:
1472:
1462:
1457:
1451:
1449:
1442:
1420:
1419:
1417:
1416:
1411:
1406:
1405:
1404:
1399:
1389:
1388:
1387:
1382:
1377:
1372:
1367:
1362:
1352:
1351:
1350:
1345:
1335:
1334:
1333:
1328:
1323:
1318:
1313:
1308:
1297:
1295:
1293:(only C and H)
1285:
1284:
1279:
1277:
1276:
1269:
1262:
1254:
1246:
1245:
1218:
1199:(3): 157–169.
1179:
1148:
1105:
1078:
1043:
1016:(4): 374–378.
998:
985:(1): 103–112.
959:
948:(2): 503–505.
930:
910:
899:
870:
841:(39): 7523–6.
821:
794:(9): 1137–46.
778:
759:(5): 825–858.
742:
693:
662:
631:
598:
561:
547:
523:
522:
520:
517:
516:
515:
510:
505:
500:
493:
490:
489:
488:
481:
474:
472:
466:
459:
457:
451:
444:
442:
433:
426:
424:
421:
414:
412:
407:
404:
398:
395:
394:
393:
354:Main article:
351:
341:
340:
339:
277:
276:
221:
220:
187:
184:
172:bioconjugation
151:synthesis and
114:coated onto a
107:
104:
81:
80:
68:
65:
15:
13:
10:
9:
6:
4:
3:
2:
2504:
2493:
2490:
2488:
2485:
2484:
2482:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2451:Semicarbazone
2449:
2447:
2446:Semicarbazide
2444:
2442:
2439:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2417:
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2389:
2387:
2384:
2382:
2379:
2377:
2376:Metfendrazine
2374:
2372:
2369:
2367:
2364:
2362:
2361:Isocarboxazid
2359:
2357:
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2312:
2309:
2307:
2306:Dihydralazine
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2256:Acylhydrazine
2254:
2252:
2249:
2248:
2245:
2241:
2234:
2229:
2227:
2222:
2220:
2215:
2214:
2211:
2197:
2194:
2192:
2189:
2188:
2187:
2186:
2182:
2180:
2179:
2175:
2170:
2169:
2166:
2160:
2157:
2155:
2152:
2150:
2147:
2145:
2142:
2140:
2137:
2135:
2132:
2131:
2129:
2125:
2115:
2112:
2108:
2105:
2104:
2103:
2100:
2096:
2093:
2092:
2091:
2088:
2084:
2081:
2079:
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2060:
2059:
2056:
2055:
2053:
2051:
2050:
2045:
2039:
2038:Telluroketone
2036:
2034:
2031:
2030:
2028:
2026:
2022:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1992:
1990:
1988:
1984:
1978:
1975:
1973:
1970:
1969:
1967:
1965:
1961:
1955:
1952:
1950:
1947:
1945:
1942:
1940:
1937:
1935:
1932:
1930:
1927:
1925:
1924:Sulfonic acid
1922:
1920:
1917:
1915:
1914:Sulfinic acid
1912:
1910:
1909:Thiosulfonate
1907:
1905:
1902:
1900:
1899:Thiosulfinate
1897:
1895:
1894:Sulfenic acid
1892:
1890:
1887:
1885:
1882:
1878:
1875:
1874:
1873:
1870:
1868:
1865:
1864:
1862:
1860:
1856:
1850:
1849:Phosphaallene
1847:
1845:
1844:Phosphaalkyne
1842:
1840:
1839:Phosphaalkene
1837:
1833:
1830:
1829:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1806:
1803:
1802:
1801:
1798:
1794:
1791:
1790:
1789:
1786:
1785:
1783:
1781:
1777:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1746:
1743:
1741:
1738:
1736:
1733:
1731:
1728:
1726:
1723:
1721:
1718:
1716:
1713:
1711:
1708:
1706:
1703:
1701:
1698:
1696:
1693:
1691:
1688:
1686:
1683:
1681:
1678:
1676:
1673:
1669:
1666:
1664:
1661:
1660:
1659:
1656:
1655:
1653:
1651:
1647:
1644:
1624:
1612:
1609:
1608:
1607:
1604:
1600:
1597:
1595:
1592:
1591:
1590:
1587:
1586:
1584:
1580:
1574:
1571:
1569:
1566:
1562:
1559:
1558:
1557:
1554:
1550:
1547:
1545:
1542:
1540:
1537:
1536:
1535:
1532:
1531:
1529:
1527:
1523:
1517:
1514:
1512:
1511:Ethylenedioxy
1509:
1505:
1502:
1500:
1497:
1496:
1495:
1492:
1488:
1485:
1483:
1480:
1479:
1478:
1475:
1471:
1468:
1467:
1466:
1463:
1461:
1458:
1456:
1453:
1452:
1450:
1446:
1443:
1437:
1431:
1426:
1421:
1415:
1412:
1410:
1407:
1403:
1400:
1398:
1395:
1394:
1393:
1390:
1386:
1383:
1381:
1378:
1376:
1373:
1371:
1368:
1366:
1363:
1361:
1358:
1357:
1356:
1353:
1349:
1346:
1344:
1341:
1340:
1339:
1336:
1332:
1329:
1327:
1324:
1322:
1319:
1317:
1314:
1312:
1309:
1307:
1304:
1303:
1302:
1299:
1298:
1296:
1290:
1286:
1282:
1275:
1270:
1268:
1263:
1261:
1256:
1255:
1252:
1241:
1237:
1233:
1229:
1222:
1219:
1214:
1210:
1206:
1202:
1198:
1194:
1190:
1183:
1180:
1175:
1171:
1167:
1163:
1159:
1152:
1149:
1144:
1140:
1136:
1132:
1128:
1124:
1120:
1116:
1109:
1106:
1101:
1097:
1093:
1089:
1082:
1079:
1074:
1070:
1066:
1062:
1058:
1054:
1047:
1044:
1039:
1035:
1031:
1027:
1023:
1019:
1015:
1011:
1010:
1002:
999:
993:
988:
984:
980:
979:
974:
972:
963:
960:
955:
951:
947:
943:
942:
934:
931:
927:(3): 362–373.
926:
922:
918:
916:
903:
900:
895:
891:
887:
883:
882:
874:
871:
866:
862:
857:
852:
848:
844:
840:
836:
832:
825:
822:
817:
813:
809:
805:
801:
797:
793:
789:
782:
779:
774:
770:
766:
762:
758:
754:
746:
743:
738:
734:
729:
724:
720:
716:
712:
708:
704:
697:
694:
689:
685:
681:
677:
673:
666:
663:
658:
654:
650:
646:
642:
635:
632:
626:
619:
615:
614:
609:
602:
599:
593:
586:
582:
581:
576:
574:
565:
562:
558:
554:
550:
548:9780471854722
544:
540:
539:
534:
528:
525:
518:
514:
511:
509:
506:
504:
501:
499:
496:
495:
491:
485:
478:
473:
469:
468:Dihydralazine
463:
458:
454:
448:
443:
440:
438:
430:
425:
418:
413:
410:
405:
403:
396:
391:
387:
386:
385:
383:
379:
375:
371:
367:
363:
357:
349:
345:
342:
337:
333:
332:
331:
329:
325:
321:
317:
313:
309:
305:
301:
297:
293:
289:
284:
282:
248:
247:
246:
244:
240:
236:
231:
229:
225:
193:
192:
191:
185:
183:
181:
177:
173:
168:
166:
162:
158:
154:
150:
147:
143:
141:
136:The compound
134:
132:
128:
124:
120:
117:
113:
105:
103:
101:
97:
93:
89:
85:
78:
74:
73:
72:
66:
64:
62:
58:
48:
44:
33:
29:
21:
2436:Procarbazine
2421:Pildralazine
2406:Pheniprazine
2345:
2183:
2176:
2090:Vinyl halide
2047:
1977:Borinic acid
1972:Boronic acid
1949:Thioxanthate
1694:
1289:Hydrocarbons
1231:
1227:
1221:
1196:
1192:
1182:
1165:
1161:
1157:
1151:
1126:
1122:
1118:
1114:
1108:
1091:
1087:
1081:
1056:
1052:
1046:
1013:
1007:
1001:
982:
978:Heterocycles
976:
970:
962:
945:
939:
933:
924:
920:
914:
902:
885:
879:
873:
838:
834:
824:
791:
787:
781:
756:
752:
745:
710:
706:
696:
679:
675:
665:
648:
644:
634:
624:
617:
611:
601:
591:
584:
578:
572:
564:
537:
533:March, Jerry
527:
498:Azo compound
484:benzophenone
436:
400:
377:
365:
361:
359:
347:
343:
315:
308:β-keto acids
285:
278:
232:
222:
189:
169:
139:
135:
109:
96:Emil Fischer
86:reacts with
82:
70:
27:
26:
2351:Iproclozide
2331:Hydralazine
2316:Endralazine
2281:Cadralazine
2154:Thiocyanate
2149:Sulfonamide
2114:Perchlorate
2102:Acyl halide
2063:Fluoroethyl
1944:Thionoester
1832:Phosphonium
1817:Phosphinate
1812:Phosphonous
1800:Phosphonate
1499:Hydroperoxy
1321:Cyclopropyl
508:Nitrosamine
2487:Hydrazones
2481:Categories
2426:Pimagedine
2401:Phenelzine
2371:Mebanazine
2356:Iproniazid
2321:Gyromitrin
2301:Daminozide
2240:Hydrazines
2058:Haloalkane
1929:Thioketone
1884:Persulfide
1780:Phosphorus
1745:Isocyanate
1735:Isonitrile
1636:or oxygen
1634:hydrogen,
1630:not being
1611:Orthoester
1504:Dioxiranes
1482:Enol ether
1370:1-Propenyl
519:References
453:Gyromitrin
411:Hydrazones
378:azaenolate
294:, and the
235:equivalent
133:detector.
123:adsorption
28:Hydrazones
2441:Safrazine
2391:Octamoxin
2386:Nialamide
2366:Isoniazid
2346:Hydrazone
2341:Hydrazine
2336:Hydrazide
2291:Carbidopa
2286:Carbazide
2271:Agaritine
2191:inorganic
2025:Tellurium
1939:Thioester
1904:Sulfoxide
1889:Disulfide
1877:Sulfonium
1827:Phosphine
1805:Phosphite
1788:Phosphate
1720:Carbamate
1695:Hydrazone
1628:element,
1626:Only one
1599:Anhydride
1338:Methylene
1143:260330996
651:: 73–77.
557:642506595
326:. With a
320:pyrazoles
186:Reactions
180:lysosomes
153:reduction
67:Synthesis
61:hydrazine
47:aldehydes
2276:Benmoxin
2172:See also
2107:Chloride
2033:Tellurol
1987:Selenium
1954:Xanthate
1668:Ammonium
1650:Nitrogen
1632:carbon,
1589:Carboxyl
1556:Aldehyde
1544:Acryloyl
1526:carbonyl
1430:hydrogen
1385:Cumulene
1213:10727205
1073:20000672
1038:11653420
1030:28338683
865:18712739
816:27226728
808:16151407
773:21585205
737:28640998
535:(1985),
492:See also
266:C=N−N=CR
241:to give
239:carbonyl
146:uncouple
92:osazones
36:RRC=N−NH
2266:Adjudin
2196:organic
1995:Selenol
1919:Sulfone
1872:Sulfide
1770:NONOate
1765:Nitroso
1755:Nitrite
1750:Nitrate
1740:Cyanate
1730:Nitrile
1715:Amidine
1710:Imidate
1680:Nitrene
1675:Hydrazo
1663:Enamine
1594:Acetoxy
1582:carboxy
1549:Benzoyl
1487:Epoxide
1470:Methoxy
1460:Alcohol
1414:Carbene
1348:Methine
1168:: 183.
1129:: 173.
856:2743602
728:5580355
406:Gallery
262:C=O → R
211:C=O + H
199:C=N−NR'
119:sorbent
43:ketones
2251:4-PTSC
2095:Iodide
2015:Selone
1859:Sulfur
1568:Ketone
1561:Ketene
1539:Acetyl
1494:Peroxy
1465:Alkoxy
1455:Acetal
1436:oxygen
1425:carbon
1409:Alkyne
1402:Benzyl
1397:Phenyl
1380:Allene
1375:Crotyl
1355:Alkene
1343:Bridge
1331:Pentyl
1316:Propyl
1306:Methyl
1211:
1141:
1071:
1036:
1028:
863:
853:
814:
806:
771:
735:
725:
555:
545:
312:azines
290:, the
254:C=N−NH
243:azines
228:oximes
157:oxygen
116:silica
2127:Other
1964:Boron
1934:Thial
1867:Thiol
1760:Nitro
1725:Imide
1705:Amide
1690:Oxime
1685:Imine
1658:Amine
1606:Ester
1573:Ynone
1477:Ether
1448:R-O-R
1423:Only
1365:Allyl
1360:Vinyl
1326:Butyl
1311:Ethyl
1301:Alkyl
1139:S2CID
1034:S2CID
888:: 3.
812:S2CID
503:Imine
300:vinyl
237:of a
224:Alkyl
215:N−NR'
207:O → R
2466:UDMH
2456:SDMH
2311:DNPH
2049:Halo
1534:Acyl
1434:and
1392:Aryl
1209:PMID
1069:PMID
1026:PMID
861:PMID
804:PMID
769:PMID
733:PMID
587:: 69
553:OCLC
543:ISBN
306:via
106:Uses
51:N−NH
45:and
2396:PEH
2381:MMH
2326:HBT
2261:ADH
1700:Azo
1236:doi
1201:doi
1170:doi
1131:doi
1096:doi
1061:doi
1057:110
1018:doi
987:doi
950:doi
925:57B
890:doi
851:PMC
843:doi
796:doi
761:doi
723:PMC
715:doi
711:117
684:doi
653:doi
620:: 3
573:via
360:In
298:to
270:+ H
258:+ R
203:+ H
176:ADC
163:in
159:in
155:of
149:ATP
2483::
1432:,
1427:,
1232:62
1230:.
1207:.
1197:33
1195:.
1191:.
1166:65
1164:.
1137:.
1127:65
1125:.
1090:.
1067:.
1055:.
1032:.
1024:.
1012:.
983:89
981:.
975:.
946:45
944:.
923:.
919:.
886:50
884:.
859:.
849:.
839:47
837:.
833:.
810:.
802:.
792:23
790:.
767:.
757:22
755:.
731:.
721:.
709:.
705:.
680:27
678:.
674:.
649:41
647:.
643:.
622:;
618:50
616:.
610:.
589:;
585:57
583:.
577:.
551:,
384:.
283:.
245::
230:.
167:.
131:UV
102:.
2232:e
2225:t
2218:v
1273:e
1266:t
1259:v
1242:.
1238::
1215:.
1203::
1176:.
1172::
1158:S
1145:.
1133::
1119:R
1115:S
1102:.
1098::
1092:8
1075:.
1063::
1040:.
1020::
1014:9
995:.
989::
971:H
956:.
952::
915:H
911:3
897:.
892::
867:.
845::
818:.
798::
775:.
763::
739:.
717::
690:.
686::
659:.
655::
629:.
596:.
437:m
366:N
364:,
362:N
348:N
346:,
344:N
318:-
316:H
274:O
272:2
268:2
264:2
260:2
256:2
252:2
250:R
217:2
213:2
209:2
205:2
201:2
197:2
195:R
140:p
53:2
38:2
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