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33:
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24:
782:
production; that waste product is the major industrial carbazole source. Polar compounds (e.g., ketones) selectively precipitate it from the anthracene; a more modern technique is simply selective crystallization from molten coal tar at high temperature or low pressure (70 mmHg).
573:
540:
1705:
834:
759:
692:
1836:
1649:
1324:
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1357:
1736:
774:
Few carbazole production methods are economically viable, due to limited demand. During coal tar distillation, carbazole concentrates in the
1051:
431:
740:
ring is fused onto the five-membered ring at the 2–3 position of indole (equivalent to the 9a–4a double bond in carbazole, respectively).
1100:
1872:
1717:
1238:
1204:
1437:"Ueber Tetra- und Hexahydrocarbazolverbindungen und eine neue Carbazolsynthese. (Mitbearbeitet von. A. Witte und W. Bothe.)"
855:
1260:
1892:
1853:
1666:
1341:
941:
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126:
797:
699:
866:
1254:
Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van
Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011).
940:. For applications that transition-metal impurities in the final product might inhibit, an alternative is
900:. The triazole is unstable and at elevated temperatures, nitrogen is released and the carbazole is formed.
849:
617:
339:
236:
564:
1614:
O. Bremer (1934). "Ăśber die
Bedeutung der Graebe-Ullmannschen Carbazolsynthese und deren Ăśbertragung auf
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Carbazoles occur naturally in carbazole alkaloids. Carbazole alkaloids with unsubstituted
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8:
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158:
102:
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1255:
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837:. In one modification, both steps are rolled into one by carrying out the reaction in
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454:
1333:
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1185:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
1179:
1061:
806:
312:
267:
1502:
1765:
1691:
897:
670:
1789:
863:
A third method for the synthesis of carbazole is the Graebe–Ullmann reaction.
1881:
1845:
1658:
1633:
1600:
1578:
1520:
1487:
1454:
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is useful in the electrical and electronic industries, and certain carbazole
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1047:
915:
911:
814:
779:
744:
605:
512:
502:
229:
635:
1293:
978:. Some carbazole alkaloids, especially glybomin B, have been isolated from
41:
1274:
1196:
1574:
1124:
1095:
In organic chemistry, carbazole proper is also an ingredient for several
838:
755:
658:
218:
1112:
775:
479:
249:
189:
1322:
Collin, Gerd; Höke, Hartmut; Talbiersky, Jörg. "Carbazole".
1230:
1145:
1116:
1108:
890:
623:
1682:
Bhanuchandra, M.; Yorimitsu Hideki. "Dibenzothiophene 5,5-dioxide".
1582:
1469:
1436:
669:
Except where otherwise noted, data are given for materials in their
1150:
1128:
903:
842:
763:
729:
715:
287:
209:
32:
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593:
125:
1089:
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725:
492:
299:
907:
Fluorescence of (9H-carbazol-9-yl)(2,4-dichlorophenyl) methanone
1647:
Vogt, Peter F.; Gerulis, John J. "Amines, Aromatic".
1140:
1043:
733:
724:. It has a tricyclic structure, consisting of two six-membered
631:
405:
InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
169:
1503:"1,2,3,4-Tetrahydrocarbazole (Carbazole, 1,2,3,4-tetrahydro-)"
1253:
1077:; in general, they are electron photodonors (hole acceptors).
415:
InChI=1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
929:
818:
323:
149:
115:
922:
to carbazoles when heated in air. A similar reaction is the
365:
23:
966:
rings occur rarely. Olivacin has been found in the bark of
732:-containing ring. The compound's structure is based on the
278:
597:
1834:
Naarmann, Herbert. "Polymers, Electrically conducting".
1681:
1573:
936:
Substituted carbazoles are most easily synthesized with
601:
1084:, which has not achieved substantial industrial use.
1541:
Wang, Zerong (2010). "Bucherer
Carbazole Synthesis".
1046:
light spectrum, they see application as pigments and
1749:
Rizzo, Carmelo J. (2005). "N-Methylcarbazole".
1704:
1227:
CRC Handbook of
Chemistry and Physics, 88th Edition
1840:. Vol. 29. Weinheim: Wiley-VCH. p. 309.
1470:"Ueber Elektrolyse des Phenols mit Wechselströmen"
841:. In the third step, this compound is oxidized by
1653:. Vol. 2. Weinheim: Wiley-VCH. p. 703.
1543:Comprehensive Organic Name Reactions and Reagents
1181:International Union of Pure and Applied Chemistry
1879:
1321:
1247:
311:
1804:Kirk-Othmer Encyclopedia of Chemical Technology
1405:Kirk-Othmer Encyclopedia of Chemical Technology
1373:Kirk-Othmer Encyclopedia of Chemical Technology
852:, which uses a naphthol and an aryl hydrazine.
643:
517:354.69 °C (670.44 °F; 627.84 K)
101:
1837:Ullmann's Encyclopedia of Industrial Chemistry
1758:Encyclopedia of Reagents for Organic Synthesis
1712:, Wiesbaden: Springer Fachmedien, p. 49,
1684:Encyclopedia of Reagents for Organic Synthesis
1650:Ullmann's Encyclopedia of Industrial Chemistry
1325:Ullmann's Encyclopedia of Industrial Chemistry
1054:production and aminoethylcarbazole is used in
728:rings fused on either side of a five-membered
647:
530:−117.4 Ă— 10 cm mol
1500:
1356:: CS1 maint: multiple names: authors list (
507:246.3 °C (475.3 °F; 519.5 K)
1467:
1698:
1434:
1371:Cofrancesco, A. J., "Anthraquinone",
1080:Carbazole electrochemically oxidizes to a
380:
239:
197:
1613:
1501:Rogers, Crosby U.; Corson, B. B. (1950).
1317:
1315:
1313:
1311:
1309:
1307:
1305:
1303:
1283:
1273:
347:
1060:
928:
902:
1812:10.1002/0471238961.1608152023011407.a01
1802:Ying Wang, "Photoconductive polymers",
1735:was invoked but never defined (see the
1646:
1381:10.1002/0471238961.0114200803150618.a01
1370:
376:
217:
1880:
1300:
1256:"Hazardous Compounds in Tobacco Smoke"
778:distillate and must be removed before
663:220 °C (428 °F; 493 K)
230:
1801:
1748:
1413:10.1002/0471238961.20011802052020.a01
1220:
1218:
1216:
1042:As carbazoles have a relatively rich
951:
408:Key: UJOBWOGCFQCDNV-UHFFFAOYSA-N
177:
157:
1833:
1806:, New York: John Wiley, p. 15,
1540:
1403:Betts, W. D., "Tar and Pitch",
1224:
1730:
1618:-substituierte Pyridino-triazole".
1407:, New York: John Wiley, p. 5,
1375:, New York: John Wiley, p. 5,
1261:Int. J. Environ. Res. Public Health
1050:. The parent carbazole is used in
938:transition metal coupling reactions
418:Key: UJOBWOGCFQCDNV-UHFFFAOYAV
302:
286:
13:
1583:"Ueber eine neue Carbazolsynthese"
1213:
1119:are all made from carbazole. The
942:nucleophilic aromatic substitution
865:
854:
796:
14:
1904:
1866:
1725:
1402:
1364:
762:first isolated the compound from
736:structure, but in which a second
1731:Cite error: The named reference
1025:
1013:
1001:
989:
677:
563:
558:
472:
466:
40:
31:
22:
1827:
1795:
1782:
1742:
1675:
1640:
1607:
1567:
1534:
1037:
673:(at 25 °C , 100 kPa).
1551:10.1002/9780470638859.conrr120
1494:
1461:
1428:
1396:
1189:The Royal Society of Chemistry
1173:
1092:are extremely heat resistant.
896:which instantaneously forms a
743:Carbazole is a constituent of
460:
1:
1334:10.1002/14356007.a05_059.pub2
1166:
769:
878:-phenyl-1,2-diaminobenzene (
859:Bucherer carbazole synthesis
850:Bucherer carbazole synthesis
792:Borsche–Drechsel cyclization
7:
1134:
1065:Pigment Violet 23 synthesis
10:
1909:
1766:10.1002/047084289X.rn00578
1692:10.1002/047084289X.rn02046
1529:, vol. 4, p. 884
1156:Polychlorinated carbazoles
955:
801:Borsche–Drechsel synthesis
750:
1893:IARC Group 2B carcinogens
1621:Justus Liebigs Ann. Chem.
1588:Justus Liebigs Ann. Chem.
1442:Justus Liebigs Ann. Chem.
667:
539:
534:
447:
427:
392:
85:
69:
53:
48:
39:
30:
21:
1846:10.1002/14356007.a21_429
1659:10.1002/14356007.a02_037
1634:10.1002/jlac.19345140116
1601:10.1002/jlac.18962910104
1521:10.15227/orgsyn.030.0090
1488:10.1002/prac.18880380105
1455:10.1002/jlac.19083590103
618:Precautionary statements
1328:. Weinheim: Wiley-VCH.
1225:Lide, David R. (2007).
870:Graebe–Ullmann reaction
848:Another classic is the
821:. The second step is a
524:Magnetic susceptibility
1066:
969:Aspidosperma olivaceum
933:
908:
889:) is converted into a
874:In the first step, an
871:
860:
827:rearrangement reaction
802:
1790:U.S. patent 4,345,074
1275:10.3390/ijerph8020613
1197:10.1039/9781849733069
1127:fuses carbazole to a
1075:light-emitting diodes
1069:Carbazoles stabilize
1064:
981:Glycosmis pentaphylla
932:
906:
869:
858:
845:to carbazole itself.
831:ring-closing reaction
817:to the corresponding
800:
790:for carbazole is the
786:A classic laboratory
497:1.301 g cm
1545:. pp. 549–552.
1468:E. Drechsel (1888).
1073:emitters in certain
439:c1ccc2c(c1)c3ccccc32
55:Preferred IUPAC name
1706:Eberhard Breitmaier
1435:W. Borsche (1908).
1161:Carbazole alkaloids
1099:. The insecticide
1097:bioactive molecules
958:Carbazole alkaloids
914:derivatives, being
835:tetrahydrocarbazole
805:In the first step,
487: g·mol
139:Beilstein Reference
18:
1086:Polyvinylcarbazole
1082:conductive polymer
1067:
975:Ochrosia elliptica
972:and ellipticin in
952:Natural Occurrence
934:
909:
872:
861:
803:
700:Infobox references
16:
1719:978-3-519-03542-8
1527:Collected Volumes
1508:Organic Syntheses
1352:cite encyclopedia
1240:978-0-8493-0488-0
1233:. pp. 3–86.
1206:978-0-85404-182-4
1056:pigment violet 23
920:naturally oxidize
887:-phenylenediamine
823:hydrochloric acid
788:organic synthesis
708:Chemical compound
706:
705:
588:Hazard statements
361:CompTox Dashboard
127:Interactive image
1900:
1860:
1859:
1831:
1825:
1824:
1799:
1793:
1792:
1786:
1780:
1779:
1754:-Methylcarbazole
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1740:
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1244:
1222:
1211:
1210:
1177:
1121:topoisomerase II
1105:cocaine overdose
1029:
1017:
1005:
993:
946:dibenzothiophene
924:Mallory reaction
722:organic compound
690:
684:
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455:Chemical formula
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1475:J. Prakt. Chem.
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1268:(12): 613–628.
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1207:
1191:. p. 212.
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807:phenylhydrazine
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76:diphenylenimine
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1579:Fritz Ullmann
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949:
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921:
917:
916:electron rich
913:
912:Diphenylamine
905:
901:
899:
895:
892:
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815:cyclohexanone
812:
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789:
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781:
780:anthraquinone
777:
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72:9-azafluorene
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1609:
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1592:
1586:
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1512:
1506:
1496:
1482:(1): 65–74.
1479:
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804:
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773:
754:
742:
719:heterocyclic
711:
710:
579:
541:
324:RTECS number
179:ChEMBL243580
86:Identifiers
70:Other names
60:
1575:Carl Graebe
1125:ellipticine
1052:Hydron Blue
1032:Glybomine B
996:Glycozoline
839:acetic acid
825:-catalyzed
760:Carl Glaser
756:Carl Graebe
659:Flash point
574:Signal word
448:Properties
237:100.001.542
159:CHEBI:27543
80:USAF EK-600
1888:Carbazoles
1882:Categories
1167:References
1123:inhibitor
1113:veterinary
1111:, and the
1044:UV-visible
1020:Ellipticin
776:anthracene
770:Production
553:Pictograms
480:Molar mass
349:0P2197HHHN
190:ChemSpider
114:3D model (
93:CAS Number
63:-Carbazole
17:Carbazole
1737:help page
1710:Alkaloide
1231:CRC Press
1146:Carboline
1117:Carprofen
1109:Rimcazole
1107:antidote
1008:Olivacine
948:dioxide.
891:diazonium
811:condensed
766:in 1872.
712:Carbazole
640:P308+P313
544:labelling
331:FE3150000
258:201-696-0
250:EC Number
1708:(1997),
1581:(1896).
1294:21556207
1183:(2014).
1151:Fluorene
1135:See also
1129:pyridine
1090:novolaks
882:-phenyl-
843:red lead
764:coal tar
730:nitrogen
716:aromatic
535:Hazards
526:(χ)
210:DrugBank
1285:3084482
1101:Nirosan
1071:triplet
964:benzene
751:History
738:benzene
726:benzene
693:what is
691: (
580:Warning
493:Density
485:167.211
300:PubChem
273:102490
219:DB07301
103:86-74-8
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1131:ring.
1115:NSAID
1103:, the
734:indole
714:is an
688:verify
685:
432:SMILES
288:C08060
170:ChEMBL
49:Names
819:imine
813:with
397:InChI
150:ChEBI
144:3956
116:JSmol
1873:MSDS
1850:ISBN
1816:ISBN
1770:ISBN
1714:ISBN
1663:ISBN
1555:ISBN
1417:ISBN
1385:ISBN
1358:link
1338:ISBN
1290:PMID
1235:ISBN
1201:ISBN
894:salt
829:and
758:and
652:P501
648:P405
644:P391
636:P281
632:P273
628:P202
624:P201
610:H413
606:H411
602:H400
598:H351
594:H341
340:UNII
313:6854
279:KEGG
199:6593
1842:doi
1808:doi
1762:doi
1688:doi
1655:doi
1630:doi
1626:514
1597:doi
1593:291
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1451:doi
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1409:doi
1377:doi
1330:doi
1280:PMC
1270:doi
1193:doi
944:on
833:to
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542:GHS
366:EPA
303:CID
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