922:
364:
235:
63:
586:
72:
54:
686:
591:
590:
589:
668:
1314:
G. W. Scherf; R. K. Brown (1960). "Potassium
Derivatives of Fluorene as Intermediates in the Preparation of C9-substituted Fluorenes. I. The Preparation of 9-fluorenyl Potassium and the Infrared Spectra of Fluorene and Some C9-substituted Fluorenes".
991:
Fluorene dyes are well developed. Most are prepared by condensation of the active methylene group with carbonyls. 2-Aminofluorene, 3,6-bis-(dimethylamino)fluorene, and 2,7-diiodofluorene are precursors to dyes.
945:
Fluorene is a precursor to other fluorene compounds; the parent species has few applications. Fluorene-9-carboxylic acid is a precursor to pharmaceuticals. Oxidation of fluorene gives
699:
1103:
Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons".
1105:
1058:
891:
react with it by adding to the 9-position. The purification of fluorene exploits its acidity and the low solubility of its sodium derivative in hydrocarbon solvents.
592:
413:
1878:
614:
1082:
1343:
Ewen, J. A.; Jones, R. L.; Razavi, A.; Ferrara, J. D. (1988). "Syndiospecific
Propylene Polymerizations with Group IVB Metallocenes".
607:
378:
1461:
1250:"Laboratory Investigation of the Products of the Incomplete Combustion of Waste Plastics and Techniques for Their Minimization"
950:
794:
1868:
1452:
1122:
1137:
Fittig, Rud. (1873), "Ueber einen neuen
Kohlenwasserstoff aus dem Diphenylenketon" Ber. Dtsch. Chem. Ges. volume 6, p. 187.
706:
980:
825:. The fluorene molecule is nearly planar, although each of the two benzene rings is coplanar with the central carbon 9.
321:
1770:
342:
894:
Both protons can be removed from C9. For example, 9,9-fluorenyldipotassium can be obtained by treating fluorene with
1066:
536:
1248:
Wang, Zhenlei; Richter, Henning; Howard, Jack B.; Jordan, Jude; Carlson, Joel; Levendis, Yiannis A. (2004-06-01).
1154:
Hicks, Latorya D.; Han, Ja Kyung; Fry, Albert J. (2000). "Hypophosphorous acid–iodine: a novel reducing system".
600:
242:
1603:
921:
555:
230:
967:
polymers (where carbon 7 of one unit is linked to carbon 2 of the next one, displacing two hydrogens) are
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1659:
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829:
523:
192:
100:
152:
1649:
1644:
1639:
1634:
1557:
1387:
1222:
818:
793:. It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a
84:
1587:
1213:
Gerkin, R. E.; Lundstedt, A. P.; Reppart, W. J. (1984). "Structure of fluorene, C13H10, at 159 K".
972:
359:
118:
1378:
Kurdyukova, I. V.; Ishchenko, A. A. (2012). "Organic dyes based on fluorene and its derivatives".
1873:
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1403:
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1118:
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958:
926:
915:
662:
62:
28:
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1395:
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1324:
1296:
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1230:
1197:
1163:
1138:
1110:
1070:
1001:
954:
758:
723:
502:
436:
805:
Although fluorene is obtained from coal tar, it can also be prepared by dehydrogenation of
330:
806:
777:. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of
212:
1391:
1226:
363:
234:
172:
128:
1806:
1801:
1715:
1684:
1618:
1613:
1506:
677:
1167:
1862:
1438:
933:
491:
481:
223:
1407:
1399:
1751:
1700:
1582:
1567:
1526:
1501:
1430:
964:
930:
888:
841:
786:
1063:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
294:
1725:
1710:
1608:
1485:
1041:
1011:
976:
884:
880:
837:
797:, the five-membered ring has no aromatic properties. Fluorene is mildly acidic.
778:
650:
626:
1287:
F. G. Bordwell (1988). "Equilibrium acidities in dimethyl sulfoxide solution".
1654:
1623:
1511:
1234:
1189:
946:
810:
513:
458:
203:
71:
40:
1273:
1175:
1142:
1114:
1847:
1837:
1832:
1761:
1669:
1577:
1521:
1021:
1016:
1006:
953:(Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc)
895:
1364:
1074:
1842:
1796:
1786:
1776:
1746:
1730:
1720:
1674:
1562:
1475:
790:
782:
613:
606:
599:
572:
36:
32:
17:
1356:
1300:
1811:
1791:
1781:
1480:
899:
833:
471:
281:
243:
1265:
1679:
1572:
1201:
911:
822:
183:
1328:
1249:
676:
Except where otherwise noted, data are given for materials in their
53:
269:
1827:
920:
305:
163:
151:
141:
1215:
814:
387:
InChI=1S/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2
260:
1434:
1427:
in the
National Institute of Standards and Technology database.
397:
InChI=1/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2
857:
738:
735:
949:, which is nitrated to give commercially useful derivatives.
347:
486:
116 to 117 °C (241 to 243 °F; 389 to 390 K)
910:
Fluorene and its derivatives can be deprotonated to give
789:
it exhibits. For commercial purposes it is obtained from
584:
809:. Alternatively, it can be prepared by the reduction of
856:
The C9-H sites of the fluorene ring are weakly acidic (
694:
741:
729:
781:. Despite its name, it does not contain the element
732:
1820:
1739:
1693:
1596:
1535:
1494:
1468:
726:
1059:International Union of Pure and Applied Chemistry
883:and has an intense orange colour. The anion is a
293:
1254:Industrial & Engineering Chemistry Research
588:
127:
1106:Ullmann's Encyclopedia of Industrial Chemistry
1446:
8:
1453:
1439:
1431:
1098:
1096:
1094:
362:
233:
211:
45:
329:
1345:Journal of the American Chemical Society
1033:
975:, and have been much investigated as a
418:
383:
358:
785:, but rather it comes from the violet
631:152 °C (306 °F; 425 K)
496:295 °C (563 °F; 568 K)
224:
390:Key: NIHNNTQXNPWCJQ-UHFFFAOYSA-N
191:
171:
105:Tricyclotrideca-2,4,6,9,11,13-hexaene
7:
801:Synthesis, structure, and reactivity
400:Key: NIHNNTQXNPWCJQ-UHFFFAOYAW
284:
268:
867:.) Deprotonation gives the stable
25:
1879:Polycyclic aromatic hydrocarbons
1462:Polycyclic aromatic hydrocarbons
828:Fluorene can be found after the
722:
684:
448:
70:
61:
52:
1400:10.1070/RC2012v081n03ABEH004211
1194:Molecular Structure of Fluorene
951:9-Fluorenylmethyl chloroformate
795:polycyclic aromatic hydrocarbon
680:(at 25 °C , 100 kPa).
1162:(41). Elsevier BV: 7817–7820.
1067:The Royal Society of Chemistry
442:
1:
1317:Canadian Journal of Chemistry
1168:10.1016/s0040-4039(00)01359-9
981:organic light-emitting diodes
1196:Nature volume 173, p. 635.
639:or concentration (LD, LC):
1895:
26:
1235:10.1107/S0108270184009963
674:
635:
566:
429:
409:
374:
111:
99:
83:
78:
69:
60:
51:
1628:-Benzopyrene(Olympicene)
1380:Russian Chemical Reviews
1143:10.1002/cber.18730060169
1115:10.1002/14356007.a13_227
657:16000 mg/kg (oral, rat)
27:Not to be confused with
1109:. Weinheim: Wiley-VCH.
969:electrically conductive
556:Magnetic susceptibility
937:
595:
1869:Molecular electronics
1604:Benzacephenanthrylene
1075:10.1039/9781849733069
924:
830:incomplete combustion
594:
101:Systematic IUPAC name
927:Kaminsky precatalyst
925:A fluorenyl-derived
819:hypophosphorous acid
577:(fire diamond)
85:Preferred IUPAC name
1588:Tricyclobutabenzene
1392:2012RuCRv..81..258K
1357:10.1021/ja00226a056
1301:10.1021/ar00156a004
1227:1984AcCrC..40.1892G
1156:Tetrahedron Letters
761:with the formula (C
503:Solubility in water
466: g·mol
421:c1ccc2c3ccccc3Cc2c1
48:
973:electroluminescent
938:
871:anion, nominally C
707:Infobox references
596:
46:
1856:
1855:
1767:Hexabenzocoronene
1650:Benzofluoranthene
1645:Benzofluoranthene
1640:Benzofluoranthene
1635:Benzofluoranthene
1558:Benzophenanthrene
1351:(18): 6255–6256.
1266:10.1021/ie030477u
1260:(12): 2873–2886.
1221:(11): 1892–1894.
1084:978-0-85404-182-4
959:peptide synthesis
916:cyclopentadienide
906:Ligand properties
898:metal in boiling
715:Chemical compound
713:
712:
663:Safety data sheet
562:-110.5·10 cm/mol
518:organic solvents
343:CompTox Dashboard
153:Interactive image
16:(Redirected from
1886:
1757:Diindenoperylene
1665:Dibenzanthracene
1660:Dibenzanthracene
1655:trans-Bicalicene
1455:
1448:
1441:
1432:
1412:
1411:
1375:
1369:
1368:
1340:
1334:
1332:
1311:
1305:
1304:
1284:
1278:
1277:
1245:
1239:
1238:
1210:
1204:
1202:10.1038/173635a0
1186:
1180:
1179:
1151:
1145:
1135:
1129:
1128:
1100:
1089:
1088:
1055:
1049:
1045:, 11th Edition,
1038:
1002:CataCXium F sulf
955:protecting group
759:organic compound
748:
747:
744:
743:
740:
737:
734:
731:
728:
697:
691:
688:
687:
616:
609:
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587:
465:
450:
444:
437:Chemical formula
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131:
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1893:
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1888:
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1885:
1884:
1883:
1859:
1858:
1857:
1852:
1821:General classes
1816:
1735:
1689:
1592:
1531:
1490:
1464:
1459:
1421:
1416:
1415:
1377:
1376:
1372:
1342:
1341:
1337:
1329:10.1139/v60-100
1313:
1312:
1308:
1295:(12): 456–463.
1286:
1285:
1281:
1247:
1246:
1242:
1212:
1211:
1207:
1187:
1183:
1153:
1152:
1148:
1136:
1132:
1125:
1102:
1101:
1092:
1085:
1069:. p. 207.
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1056:
1052:
1039:
1035:
1030:
998:
989:
943:
908:
878:
874:
861:
854:
807:diphenylmethane
803:
776:
772:
768:
764:
725:
721:
716:
709:
704:
703:
702: ?)
693:
689:
685:
681:
654:
648:
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620:
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44:
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11:
5:
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1845:
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1824:
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1815:
1814:
1809:
1807:Trinaphthylene
1804:
1802:Superphenalene
1799:
1794:
1789:
1784:
1779:
1774:
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1759:
1754:
1749:
1743:
1741:
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1718:
1716:Dibenzopyrenes
1713:
1708:
1703:
1697:
1695:
1691:
1690:
1688:
1687:
1685:Tetraphenylene
1682:
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1543:Benzanthracene
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1537:
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1514:
1509:
1507:Acenaphthylene
1504:
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1386:(3): 258–290.
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1289:Acc. Chem. Res
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1706:Benzoperylene
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1554:
1553:Benzofluorene
1551:
1549:
1548:Benzofluorene
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987:Fluorene dyes
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957:on amines in
956:
952:
948:
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934:polypropylene
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669:Sigma-Aldrich
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1752:Dicoronylene
1701:Anthanthrene
1625:
1583:Triphenylene
1568:Fluoranthene
1527:Phenanthrene
1516:
1502:Acenaphthene
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965:Polyfluorene
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787:fluorescence
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306:RTECS number
112:Identifiers
90:
1726:Triangulene
1711:Corannulene
1619:Benzopyrene
1614:Benzopyrene
1609:Benzopyrene
1486:Naphthalene
1042:Merck Index
1012:Indecainide
977:luminophore
885:nucleophile
879:, which is
779:naphthalene
651:median dose
637:Lethal dose
627:Flash point
508:1.992 mg/L
476:1.202 g/mL
430:Properties
231:100.001.541
193:ChEMBL16236
173:CHEBI:28266
1863:Categories
1771:Hexa-cata-
1512:Anthracene
1190:John Iball
1124:3527306730
1028:References
947:fluorenone
863:= 22.6 in
811:fluorenone
514:Solubility
459:Molar mass
331:3Q2UY0968A
204:ChemSpider
140:3D model (
119:CAS Number
41:Fluorenone
1874:Fluorenes
1848:Phenacene
1838:Cyclacene
1833:Circulene
1762:Heptacene
1670:Pentacene
1578:Tetracene
1522:Phenalene
1274:0888-5885
1176:0040-4039
1022:Carbazole
1017:PD-137889
1007:Fluorenol
896:potassium
869:fluorenyl
755:-fluorene
313:LL5670000
252:201-695-5
244:EC Number
93:-Fluorene
47:Fluorene
18:Fluorenyl
1843:Helicene
1797:Sumanene
1787:Rubicene
1777:Kekulene
1747:Coronene
1740:7+ rings
1731:Zethrene
1721:Hexacene
1675:Perylene
1563:Chrysene
1517:Fluorene
1476:Butalene
1425:Fluorene
1408:95312830
1365:22148816
1192:(1954),
1061:(2014).
996:See also
914:akin to
881:aromatic
836:such as
834:plastics
791:coal tar
783:fluorine
719:Fluorene
574:NFPA 704
567:Hazards
558:(χ)
37:Fluorone
33:Fluorine
29:Fluorane
1812:Truxene
1792:Rubrene
1782:Ovalene
1694:6 rings
1597:5 rings
1536:4 rings
1495:3 rings
1481:Azulene
1469:2 rings
1388:Bibcode
1323:: 697.
1223:Bibcode
912:ligands
900:dioxane
852:Acidity
700:what is
698: (
537:Acidity
472:Density
464:166.223
282:PubChem
129:86-73-7
1680:Picene
1573:Pyrene
1406:
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1081:
823:iodine
757:is an
695:verify
692:
665:(SDS)
414:SMILES
270:C07715
184:ChEMBL
79:Names
1828:Acene
1404:S2CID
813:with
749:, or
549:22.6
531:4.18
379:InChI
164:ChEBI
142:JSmol
39:, or
1361:PMID
1270:ISSN
1172:ISSN
1119:ISBN
1079:ISBN
1047:4081
971:and
941:Uses
865:DMSO
844:and
815:zinc
524:log
322:UNII
295:6853
261:KEGG
213:6592
1396:doi
1353:doi
1349:110
1325:doi
1297:doi
1262:doi
1231:doi
1198:doi
1164:doi
1139:doi
1111:doi
1071:doi
979:in
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846:PVC
832:of
817:or
736:ʊər
348:EPA
285:CID
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449:H
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