387:
236:
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40:
810:
738:
31:
55:
1434:, is the only name in the class of ethers which is retained both as a preferred IUPAC name and for use in general nomenclature. For preferred IUPAC names, no substitution is allowed; for general nomenclature substitution is allowed on the ring and on the side chain under certain conditions (see P-34.1.1.4).
736:
602:
569:
754:
684:
1553:
Helmut Fiege; Heinz-Werner Voges; Toshikazu
Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus. "Phenol Derivatives".
1328:, the word "anisole" is the 39th-most-likely word (out of over 25,000 possibilities) for a "bingo"/"bonus", i.e. the deployment of all seven letters in one's own hand simultaneously.
680:
823:
1555:
739:
436:
1649:
761:
1476:
I. Thomsen; K. Clausen; S. Scheibye; S.-O. Lawesson (1984). "Thiation with 2,4-Bis(4-Methoxyphenyl)-1,3,2,4-Dithiadiphosphetane 2,4-Disulfide:
644:
1532:
1461:
1412:
945:
1572:
401:
1691:
1588:
A. J. Birch and K. B. Chamberlain (1977). "TricarbonylIron and
TricarbonylIron(1+) Hexafluorophosphate(1−) from Anisole".
672:
638:
334:
960:
directing group, which means that electrophilic substitution preferentially occurs at these three sites. The enhanced
957:
365:
1077:
Unlike most acetophenones, but reflecting the influence of the methoxy group, methoxyacetophenone undergoes a second
593:
1722:
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1393:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
141:
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1004:
961:
925:) group attached. Anisole is a standard reagent of both practical and pedagogical value.
676:
262:
213:
972:
group, which renders the ring more electron-rich. The methoxy group strongly affects the
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Also indicating an electron-rich ring, anisole readily forms π-complexes with
883:
seed, and in fact many of its derivatives are found in natural and artificial
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Except where otherwise noted, data are given for materials in their
1524:
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of 3700 mg/kg in rats. Its main hazard is its flammability.
892:
880:
318:
164:
140:
130:
30:
1453:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
1081:. Many related reactions have been demonstrated. For example,
876:
273:
370:
38:
29:
731:
1507:
E. Peter Kündig (2004). "Synthesis of
Transition Metal
818:
891:
to other synthetic compounds. Structurally, it is an
887:. The compound is mainly made synthetically and is a
16:
Organic compound (CH₃OC₆H₅) also named methoxybenzene
1666:"Fun with analytics: Probabilities and Scrabble"
306:
1615:G. S. Hiers and F. D. Hager (1929). "Anisole".
1199:of anisole gives 1-methoxycyclohexa-1,4-diene.
735:
116:
1556:Ullmann's Encyclopedia of Industrial Chemistry
1456:(6th ed.), New York: Wiley-Interscience,
8:
1140:The ether linkage is highly stable, but the
1387:
1385:
1383:
410:InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
1144:can be removed with strong acids, such as
420:InChI=1/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
385:
234:
212:
18:
1548:
1546:
1544:
952:, which in turn reacts more quickly than
342:
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1023:
984:electron withdrawing group despite the
921:
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906:
867:
863:
859:
1692:International Chemical Safety Card 1014
1379:
1307:Anisole is relatively nontoxic with an
441:
406:
381:
1642:
1640:
1515:. Topics in Organometallic Chemistry.
1207:Anisole is prepared by methylation of
530:154 °C (309 °F; 427 K)
520:−37 °C (−35 °F; 236 K)
225:
932:; sodium phenoxide is reacted with a
413:Key: RDOXTESZEPMUJZ-UHFFFAOYSA-N
192:
172:
7:
1000:-substitution of anisole is –0.27.
992:. Stated more quantitatively, the
980:electron donor, more so than as an
946:electrophilic aromatic substitution
423:Key: RDOXTESZEPMUJZ-UHFFFAOYAP
297:
281:
14:
948:reaction at a faster speed than
808:
592:
587:
471:
53:
804:(at 25 °C , 100 kPa).
1397:The Royal Society of Chemistry
968:reflects the influence of the
477:
465:
1:
1405:10.1039/9781849733069-00648
776:or concentration (LD, LC):
25:
1744:
1399:. 2014. pp. 702–703.
1299:is prepared from anisole.
1283:Anisole is a precursor to
956:. The methoxy group is an
930:Williamson ether synthesis
928:It can be prepared by the
1480:-Methylthiopyrrolidone".
1295:. For example, synthetic
798:
772:
568:
563:
452:
432:
397:
100:
90:
78:
66:
61:
52:
24:
1699:pheromone database entry
1631:10.15227/orgsyn.009.0012
1602:10.15227/orgsyn.057.0107
1565:10.1002/14356007.a19_313
1494:10.15227/orgsyn.062.0158
1348:Butylated hydroxyanisole
639:Precautionary statements
1559:. Weinheim: Wiley-VCH.
1083:phosphorus pentasulfide
794:3700 mg/kg (rat, oral)
547:Magnetic susceptibility
1368:2,4,6-Trichloroanisole
1096:) converts anisole to
1007:, anisole reacts with
742:
43:
34:
1652:July 1, 2010, at the
1513:Topics Organomet Chem
1014:4-methoxyacetophenone
871:. It is a colorless
741:
80:Systematic IUPAC name
42:
33:
1003:Illustrative of its
724:(fire diamond)
68:Preferred IUPAC name
1511:-Arene Complexes".
1446:Smith, Michael B.;
492: g·mol
154:Beilstein Reference
93:Methyl phenyl ether
21:
1358:Ethyl phenyl ether
1322:In the board game
1098:Lawesson's reagent
944:Anisole undergoes
936:to yield anisole.
831:Infobox references
743:
44:
35:
19:
1723:Methoxy compounds
1670:www.illumine8.com
1618:Organic Syntheses
1590:Organic Syntheses
1534:978-3-540-01604-5
1482:Organic Syntheses
1463:978-0-471-72091-1
1414:978-0-85404-182-4
1150:boron trichloride
1132:Cr(η-anisole)(CO)
986:electronegativity
976:of the ring as a
839:Chemical compound
837:
836:
617:Hazard statements
500:Colorless liquid
366:CompTox Dashboard
142:Interactive image
48:
47:
1735:
1728:Phenyl compounds
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1213:dimethyl sulfate
1209:sodium phenoxide
1192:
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1017:
1009:acetic anhydride
994:Hammett constant
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851:organic compound
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1005:nucleophilicity
964:of anisole vs.
962:nucleophilicity
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923:
919:
915:
908:
904:
896:
879:reminiscent of
869:
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1574:978-3527306732
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802:standard state
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95:Phenoxymethane
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84:Methoxybenzene
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934:methyl halide
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526:Boiling point
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516:Melting point
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1673:. Retrieved
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1502:
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1471:
1452:
1448:March, Jerry
1441:
1418:
1392:
1370:(cork taint)
1343:Bromoanisole
1323:
1321:
1306:
1282:
1279:Applications
1206:
1195:
1142:methyl group
1139:
1125:
1076:
1002:
997:
954:nitrobenzene
943:
927:
846:
842:
841:
773:
720:
608:
570:
319:RTECS number
194:ChEMBL278024
101:Identifiers
91:Other names
1203:Preparation
1079:acetylation
788:median dose
774:Lethal dose
603:Signal word
510:0.995 g/cm
497:Appearance
453:Properties
232:100.002.615
174:CHEBI:16579
1718:Pheromones
1707:Categories
1675:2023-12-08
1375:References
1289:pheromones
958:ortho/para
940:Reactivity
885:fragrances
582:Pictograms
540:Insoluble
536:Solubility
485:Molar mass
444:COc1ccccc1
344:B3W693GAZH
205:ChemSpider
129:3D model (
108:CAS Number
1697:Pherobase
1419:Anisole,
1287:, insect
982:inductive
978:mesomeric
899:) with a
889:precursor
853:with the
709:P403+P235
705:P370+P378
697:P337+P313
693:P332+P313
677:P302+P352
573:labelling
355:UN number
326:BZ8050000
253:202-876-1
245:EC Number
1650:Archived
1519:: 3–20.
1450:(2007),
1338:Anethole
1332:See also
1325:Scrabble
1297:anethole
1285:perfumes
1251:→ 2 C
1102:[(CH
1011:to give
974:pi cloud
849:, is an
721:NFPA 704
564:Hazards
549:(χ)
118:100-66-3
20:Anisole
1713:Flavors
1596:: 107.
1488:: 158.
1130:, e.g.
988:of the
970:methoxy
966:benzene
950:benzene
875:with a
855:formula
843:Anisole
824:what is
822: (
609:Warning
506:Density
490:108.140
295:PubChem
159:506892
72:Anisole
1625:: 12.
1571:
1531:
1460:
1411:
1363:Phenol
1303:Safety
1291:, and
1060:C(O)CH
990:oxygen
912:phenyl
910:) and
901:methyl
873:liquid
819:verify
816:
554:−72.79
437:SMILES
283:C01403
185:ChEMBL
62:Names
1429:−O−CH
1353:Ether
1211:with
1046:→
893:ether
881:anise
877:smell
845:, or
402:InChI
359:2222
268:2964
165:ChEBI
131:JSmol
1647:MSDS
1569:ISBN
1529:ISBN
1458:ISBN
1409:ISBN
1234:O Na
1071:COOH
998:para
996:for
713:P501
701:P362
689:P321
673:P280
669:P264
665:P243
661:P242
657:P241
653:P240
649:P233
645:P210
631:H319
627:H315
623:H226
335:UNII
308:7519
274:KEGG
214:7238
1627:doi
1598:doi
1561:doi
1521:doi
1490:doi
1401:doi
1263:+
1259:OCH
1238:(CH
1236:+
1215:or
1175:HOC
1173:→
1148:or
1114:)PS
1065:+
1040:CO)
1036:(CH
1034:+
905:−CH
897:−O−
571:GHS
371:EPA
298:CID
1709::
1668:.
1639:^
1621:.
1594:57
1592:.
1567:.
1543:^
1527:.
1486:62
1484:.
1417:.
1407:.
1382:^
1311:50
1309:LD
1269:SO
1265:Na
1246:SO
1242:O)
1224:2
1219::
1186:CH
1184:+
1171:HI
1169:+
1161:OC
1157:CH
1152::
1137:.
1123:.
1106:OC
1100:,
1093:10
1067:CH
1052:OC
1048:CH
1026:OC
1022:CH
916:−C
862:OC
858:CH
784:50
782:LD
711:,
707:,
703:,
699:,
695:,
691:,
687:,
683:,
679:,
675:,
671:,
667:,
663:,
659:,
655:,
651:,
647:,
629:,
625:,
575::
1678:.
1634:.
1629::
1623:9
1604:.
1600::
1577:.
1563::
1537:.
1523::
1517:7
1509:η
1496:.
1492::
1478:N
1431:3
1427:5
1425:H
1423:6
1421:C
1403::
1271:4
1267:2
1261:3
1257:5
1255:H
1253:6
1248:2
1244:2
1240:3
1232:5
1230:H
1228:6
1226:C
1190:I
1188:3
1181:5
1179:H
1177:6
1167:5
1165:H
1163:6
1159:3
1134:3
1120:2
1118:]
1116:2
1112:4
1110:H
1108:6
1104:3
1091:S
1089:4
1087:P
1085:(
1069:3
1062:3
1058:4
1056:H
1054:6
1050:3
1044:O
1042:2
1038:3
1032:5
1030:H
1028:6
1024:3
1016::
922:5
920:H
918:6
914:(
907:3
903:(
895:(
868:5
866:H
864:6
860:3
814:Y
790:)
786:(
762:0
755:2
748:1
556:×
478:O
475:8
472:H
469:7
466:C
373:)
369:(
133:)
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