1004:
368:
237:
1028:
1052:
629:
1072:
624:
634:
609:
619:
614:
24:
896:
1102:
position means the second ring needs to start from two equatorial bonds (blue) of the first ring. A six-membered ring does not offer sufficient space to start out on an axial position (upwards), and reach the axial position of the neighboring carbon atom, which then will be on the downwards side of
642:
589:
1343:
Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons".
772:
760:
909:
1345:
1452:
1003:
993:-Decalin is a chiral molecule without a chiral center; it has a two-fold rotational symmetry axis, but no reflective symmetry. However, the
417:
1378:
Isa, Khairuddin Md; Abdullah, Tuan Amran Tuan; Ali, Umi Fazara Md (2018). "Hydrogen donor solvents in liquefaction of biomass: A review".
768:
1282:
1264:
704:
1325:
1295:
1027:
120:
1107:
in figure 5). The structure is conformationally frozen. It does not have the ability to undergo a chair flip as in the
382:
109:
904:
916:
1362:
1510:
1071:
764:
698:
315:
232:
633:
194:
346:
1459:
748:
628:
1248:
623:
1051:
752:
244:
1245:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
838:
808:
363:
1520:
543:
98:
608:
1311:
613:
1123:(such as figure 6) that play a key role in the signalling between distantly separated cells.
994:
716:
656:
601:
997:
is canceled through a chair-flipping process that turns the molecule into its mirror image.
1174:
Decalin itself is rare in nature but several decalin derivatives are known. They arise via
1037:
618:
324:
36:
784:
756:
214:
8:
1476:
978:
967:
64:
1490:
857:
367:
236:
174:
163:
152:
74:
1453:"PDF – Surrogate JP-8 Aviation Fuel Study – Alessandro Agosta Thesis Drexel University"
986:
724:
132:
1515:
1434:
1358:
1291:
1260:
851:
1329:
1424:
1387:
1350:
1252:
1206:
947:
776:
565:
531:
456:
686:
288:
263:
1256:
1166:
in a fused state with hydrogen in the presence of a copper or nickel catalyst.
712:
1391:
1154:. This interconversion has been considered in the context of hydrogen storage.
887:
812:
732:
728:
1504:
1354:
1194:
1147:
1132:
954:. A colorless liquid with an aromatic odor, it is used as a solvent for many
740:
690:
518:
506:
225:
670:
1438:
1136:
973:
23:
800:
1221:
1163:
1143:
1104:
874:
827:
788:
1429:
1412:
1179:
780:
478:
245:
205:
796:
1287:
1191:
674:
335:
886:
Except where otherwise noted, data are given for materials in their
1211:
1151:
1120:
944:
878:
820:
119:
108:
97:
1175:
1116:
1112:
951:
736:
496:
275:
1098:
The only possible way to join the two six-membered rings in the
1413:"Natural products containing 'decalin' motif in microorganisms"
1216:
744:
185:
955:
299:
143:
87:
1342:
708:
351:
720:
662:
391:
InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2
401:
InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2
1411:
Li, Gang; Kusari, Souvik; Spiteller, Michael (2014).
792:
1135:, which rearranges to cyclodecenone, a precursor to
985:form is energetically more stable because of fewer
666:
511:trans: −30.4 °C (−22.7 °F, 242.7 K)
1410:
513:cis: −42.9 °C (−45.2 °F, 230.3 K)
1502:
682:
287:
804:
73:
1377:
1346:Ullmann's Encyclopedia of Industrial Chemistry
816:
678:
1239:
1237:
1131:Oxygenation of decalin gives the tertiary
366:
235:
213:
1428:
1286:(91 ed.). Boca Raton, Florida, USA:
323:
1380:Renewable and Sustainable Energy Reviews
1234:
362:
1503:
1279:
846:250 °C (482 °F; 523 K)
226:
1197:upon storage in the presence of air.
832:57 °C (135 °F; 330 K)
394:Key: NNBZCPXTIHJBJL-UHFFFAOYSA-N
193:
173:
162:
151:
1115:this fixation is widely used in the
1142:Decalin is the saturated analog of
404:Key: NNBZCPXTIHJBJL-UHFFFAOYAH
278:
13:
1336:
14:
1532:
1283:Handbook of Chemistry and Physics
1090:
1070:
1050:
1026:
1002:
894:
632:
627:
622:
617:
612:
607:
468:
22:
1483:
1469:
1251:. 2014. pp. 33, 394, 601.
1146:and can be prepared from it by
1103:the molecule (see the model of
890:(at 25 °C , 100 kPa).
254:202-046-9, 207-770-9, 207-771-4
1445:
1404:
1398:
1371:
1318:
1304:
1273:
1249:The Royal Society of Chemistry
462:
1:
1227:
1169:
1157:
1126:
7:
1280:Haynes, William M. (2010).
1257:10.1039/9781849733069-FP001
1200:
10:
1537:
1392:10.1016/j.rser.2017.04.006
961:
483:138.25 g/mol
1185:
884:
863:
588:
583:
449:
413:
378:
57:
47:
35:
30:
21:
1355:10.1002/14356007.a13_227
699:Precautionary statements
553:−107.7·10 cm/mol (trans)
1491:"MSDS Sheet – JT Baker"
1349:. Weinheim: Wiley-VCH.
1326:"Fuel Additive Product"
1178:-derived precursors or
544:Magnetic susceptibility
1119:skeleton to construct
556:−107.0·10 cm/mol (cis)
523:trans: 187 °C (369 °F)
1190:Decalin easily forms
1150:in the presence of a
525:cis: 196 °C (384 °F)
1511:Hydrocarbon solvents
1038:ball-and-stick model
958:or fuel additives.
933:decahydronaphthalene
41:Decahydronaphthalene
37:Preferred IUPAC name
987:steric interactions
950:, is an industrial
532:Solubility in water
441:: C1CC2CCCC2C1
433:: C1CC2CCCC2C1
133:Beilstein Reference
18:
1430:10.1039/C4NP00031E
1084:-decalin ring-flip
966:Decalin occurs in
917:Infobox references
864:Related compounds
16:
1477:"Inchem.org Data"
1290:. p. 3-134.
1266:978-0-85404-182-4
925:Chemical compound
923:
922:
870:Related compounds
852:Safety data sheet
657:Hazard statements
491:colorless liquid
347:CompTox Dashboard
121:Interactive image
110:Interactive image
99:Interactive image
1528:
1495:
1494:
1487:
1481:
1480:
1473:
1467:
1466:
1464:
1458:. Archived from
1457:
1449:
1443:
1442:
1432:
1423:(9): 1175–1201.
1408:
1402:
1396:
1395:
1375:
1369:
1368:
1340:
1334:
1333:
1328:. Archived from
1322:
1316:
1315:
1312:"Dictionary.com"
1308:
1302:
1301:
1297:978-1-43982077-3
1277:
1271:
1270:
1241:
1207:Perfluorodecalin
1074:
1054:
1030:
1006:
948:organic compound
935:, also known as
907:
901:
898:
897:
822:
818:
814:
810:
806:
802:
798:
794:
790:
786:
782:
778:
774:
770:
766:
762:
758:
754:
750:
746:
742:
738:
734:
730:
726:
722:
718:
714:
710:
706:
692:
688:
684:
680:
676:
672:
668:
664:
636:
631:
626:
621:
616:
611:
566:Refractive index
470:
464:
457:Chemical formula
371:
370:
355:
353:
327:
291:
280:
264:Gmelin Reference
247:
239:
228:
217:
197:
177:
166:
155:
123:
112:
101:
77:
26:
19:
15:
1536:
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1531:
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1529:
1527:
1526:
1525:
1501:
1500:
1499:
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1470:
1462:
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1450:
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1409:
1405:
1399:
1376:
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1365:
1341:
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1324:
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1319:
1310:
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1305:
1298:
1278:
1274:
1267:
1243:
1242:
1235:
1230:
1203:
1188:
1172:
1160:
1129:
1096:
1086:
1085:
1075:
1066:
1065:
1055:
1046:
1045:
1031:
1022:
1021:
1020:(right) isomers
1007:
964:
926:
919:
914:
913:
912: ?)
903:
899:
895:
891:
871:
843:
840:
701:
659:
645:
604:
576:
574:
559:
547:
534:
524:
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473:
467:
459:
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374:
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349:
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294:
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266:
257:
220:
200:
180:
135:
126:
91:
80:
67:
53:
51:
43:
42:
12:
11:
5:
1534:
1524:
1523:
1521:Bicycloalkanes
1518:
1513:
1497:
1496:
1482:
1468:
1465:on 2010-06-19.
1444:
1417:Nat. Prod. Rep
1403:
1397:
1370:
1363:
1335:
1332:on 2009-03-12.
1317:
1303:
1296:
1272:
1265:
1232:
1231:
1229:
1226:
1225:
1224:
1219:
1214:
1209:
1202:
1199:
1195:hydroperoxides
1187:
1184:
1171:
1168:
1159:
1156:
1128:
1125:
1095:
1089:
1088:
1087:
1080:
1076:
1069:
1067:
1060:
1056:
1049:
1047:
1036:
1032:
1025:
1023:
1009:
1008:
1001:
963:
960:
939:and sometimes
924:
921:
920:
915:
893:
892:
888:standard state
885:
882:
881:
872:
869:
866:
865:
861:
860:
855:
848:
847:
844:
837:
834:
833:
830:
824:
823:
773:P305+P351+P338
761:P303+P361+P353
757:P301+P330+P331
702:
697:
694:
693:
660:
655:
652:
651:
646:
641:
638:
637:
605:
600:
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474:
471:
465:
460:
455:
452:
451:
447:
446:
444:
443:
437:
435:
429:
427:
425:C1CCC2CCCCC2C1
424:
416:
415:
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410:
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403:
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28:
27:
9:
6:
4:
3:
2:
1533:
1522:
1519:
1517:
1514:
1512:
1509:
1508:
1506:
1492:
1486:
1478:
1472:
1461:
1454:
1448:
1440:
1436:
1431:
1426:
1422:
1418:
1414:
1407:
1401:
1393:
1389:
1386:: 1259–1268.
1385:
1381:
1374:
1366:
1360:
1356:
1352:
1348:
1347:
1339:
1331:
1327:
1321:
1313:
1307:
1299:
1293:
1289:
1285:
1284:
1276:
1268:
1262:
1258:
1254:
1250:
1247:. Cambridge:
1246:
1240:
1238:
1233:
1223:
1220:
1218:
1215:
1213:
1210:
1208:
1205:
1204:
1198:
1196:
1193:
1183:
1181:
1177:
1167:
1165:
1162:Treatment of
1155:
1153:
1149:
1148:hydrogenation
1145:
1140:
1138:
1134:
1133:hydroperoxide
1124:
1122:
1118:
1114:
1110:
1106:
1101:
1093:
1083:
1079:
1073:
1068:
1063:
1059:
1053:
1048:
1043:
1039:
1035:
1029:
1024:
1019:
1015:
1012:
1005:
1000:
999:
998:
996:
992:
988:
984:
980:
977:
976:
971:
970:
959:
957:
953:
949:
946:
942:
938:
937:bicyclodecane
934:
930:
918:
911:
906:
889:
883:
880:
876:
873:
868:
867:
862:
859:
856:
853:
850:
849:
845:
842:
836:
835:
831:
829:
826:
825:
703:
700:
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695:
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644:
640:
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635:
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603:
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582:
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562:
555:
552:
551:
549:
545:
541:
540:
536:
533:
529:
528:
522:
520:
519:Boiling point
517:
516:
510:
508:
507:Melting point
505:
504:
500:
498:
495:
494:
490:
487:
486:
482:
480:
477:
476:
461:
458:
454:
453:
448:
440:
436:
432:
428:
423:
422:
419:
412:
398:
388:
387:
384:
377:
369:
365:
364:DTXSID1024912
361:
360:
358:
348:
344:
343:
339:
337:
334:
333:
326:
322:
321:
319:
317:
314:
313:
306:
305:
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297:
290:
286:
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277:
273:
272:
268:
265:
261:
260:
253:
252:
250:
248:
243:
242:
238:
234:
231:
229:
227:ECHA InfoCard
224:
223:
216:
212:
211:
209:
207:
204:
203:
196:
195:ChEMBL1491920
192:
191:
189:
187:
184:
183:
176:
171:
168:
165:
160:
157:
154:
150:
149:
147:
145:
142:
141:
137:
134:
130:
129:
122:
117:
114:
111:
106:
103:
100:
96:
95:
93:
89:
84:
83:
76:
72:
71:
69:
66:
62:
61:
56:
50:Bicyclodecane
46:
38:
34:
29:
25:
20:
1485:
1471:
1460:the original
1447:
1420:
1416:
1406:
1400:
1383:
1379:
1373:
1344:
1338:
1330:the original
1320:
1306:
1281:
1275:
1244:
1189:
1173:
1161:
1141:
1137:sebacic acid
1130:
1108:
1099:
1097:
1091:
1081:
1077:
1061:
1057:
1041:
1033:
1017:
1013:
1010:
990:
982:
974:
968:
965:
940:
936:
932:
928:
927:
858:Decalin MSDS
839:Autoignition
648:
590:
569:
438:
430:
300:RTECS number
169:
158:
115:
104:
58:Identifiers
48:Other names
1222:Naphthalene
1180:polyketides
1164:naphthalene
1144:naphthalene
1111:isomer. In
1105:cyclohexane
1016:(left) and
875:Naphthalene
841:temperature
828:Flash point
643:Signal word
501:0.896 g/cm
488:Appearance
450:Properties
233:100.001.861
175:CHEBI:38863
164:CHEBI:38860
153:CHEBI:38853
1505:Categories
1364:3527306730
1228:References
1170:Occurrence
1158:Derivation
602:Pictograms
537:Insoluble
479:Molar mass
325:88451Q4XYF
206:ChemSpider
86:3D model (
65:CAS Number
1288:CRC Press
1192:explosive
1127:Reactions
1121:molecules
995:chirality
813:P403+P235
809:P403+P233
801:P370+P378
769:P304+P340
765:P304+P312
753:P301+P310
593:labelling
336:UN number
307:QJ3150000
246:EC Number
1516:Decalins
1439:24984916
1212:Tetralin
1201:See also
1152:catalyst
1094:-Decalin
1064:-decalin
1044:-decalin
945:bicyclic
941:decaline
879:Tetralin
584:Hazards
546:(χ)
17:Decalin
1176:terpene
1117:steroid
1113:biology
962:Isomers
952:solvent
929:Decalin
910:what is
908: (
497:Density
276:PubChem
269:185147
172::
161::
138:878165
118::
107::
75:91-17-8
52:Decalin
1437:
1361:
1294:
1263:
1217:Dialin
1186:Safety
981:. The
956:resins
905:verify
902:
854:(SDS)
649:Danger
579:1.481
418:SMILES
186:ChEMBL
31:Names
1463:(PDF)
1456:(PDF)
1100:trans
1092:trans
1062:trans
1014:trans
983:trans
979:forms
975:trans
943:), a
439:trans
383:InChI
340:1147
170:trans
144:ChEBI
116:trans
88:JSmol
1435:PMID
1359:ISBN
1292:ISBN
1261:ISBN
972:and
821:P501
817:P405
805:P391
797:P363
793:P331
789:P321
785:P312
781:P311
777:P310
749:P280
745:P273
741:P271
737:P264
733:P261
729:P260
725:P243
721:P242
717:P241
713:P240
709:P233
705:P210
691:H411
687:H410
683:H332
679:H331
675:H314
671:H305
667:H302
663:H226
316:UNII
289:7044
215:6777
1425:doi
1388:doi
1351:doi
1253:doi
1109:cis
1082:cis
1042:cis
1040:of
1018:cis
991:cis
969:cis
591:GHS
431:cis
352:EPA
279:CID
159:cis
105:cis
1507::
1433:.
1421:31
1419:.
1415:.
1384:81
1382:.
1357:.
1259:.
1236:^
1182:.
1139:.
1078:4:
1058:3:
1034:2:
1011:1:
989:.
877:;
819:,
815:,
811:,
807:,
803:,
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1493:.
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1314:.
1300:.
1269:.
1255::
931:(
900:Y
575:)
573:D
570:n
568:(
469:H
463:C
354:)
350:(
90:)
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