1338:
259:
37:
46:
529:
524:
24:
678:
930:
936:
BASF has used 1-methylimidazole as a means to remove acid during their industrial-scale production of diethoxyphenylphosphine. In this biphasic acid scavenging using ionic liquids (BASIL) process, 1-methylimidazole reacts with HCl to produce 1-methylimidazolium hydrochloride, which spontaneously
899:
1-Methylimidazole is also the precursor for the synthesis of the methylimidazole monomer of pyrrole-imidazole polyamides. These polymers can selectively bind specific sequences of double-stranded DNA by intercalating in a sequence dependent manner.
743:. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.
759:
cannot tautomerize. It is slightly more basic than imidazole, as indicated by the pKa's of the conjugate acids of 7.0 and 7.4. Methylation also provides a significantly lower melting point, which makes 1-methylimidazole a useful solvent.
537:
504:
852:-like nitrogen and subsequent deprotonation. Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation.
615:
607:
1351:
Reedijk,R. (1969). "Pyrazoles and imidazoles as ligands. II. Coordination compounds of N-methyl imidazole with metal perchlorates and tetrafluoroborates".
691:
1074:
917:
1258:
Dupont, J.; Consorti, C.; Suarez, P.; de Souza, R. (2002). "Preparation of 1-Butyl-3-methyl imidazolium-based Room
Temperature Ionic Liquids".
1113:
896:
In the research laboratory, 1-methylimidazole and related derivatives have been used as mimic aspects of diverse imidazole-based biomolecules.
408:
611:
781:
1242:
686:
1091:
1176:
1160:
1144:
1060:
373:
698:
595:
573:
321:
254:
1171:
Gupta, R. R., Kumar, M., Gupta, V., Heterocyclic
Chemistry II: Five Membered Heterocycles; 1999 Springer,
342:
591:
528:
196:
1010:
266:
1337:
359:
137:
1009:. 1-methylimidazole forms adducts with Lewis acids such as molybdenum perfluorobutyrate and
523:
551:
516:
1139:
Gilchrist, T. L., Heterocyclic
Chemistry, 2nd ed.; 1992 Longman Scientific & Technical,
1300:
330:
144:
64:
623:
599:
216:
8:
1384:
1189:
1072:
Ebel, K.; Koehler, H.; Gamer, A. O. & Jäckh, R. (2002). "Imidazole and
Derivatives".
258:
176:
113:
103:
1304:
1321:
1288:
156:
1364:
660:
1389:
1326:
1260:
1238:
1172:
1156:
1140:
1087:
1056:
1036:
654:
1360:
1316:
1308:
1293:
Proceedings of the Royal
Society A: Mathematical, Physical and Engineering Sciences
1269:
1230:
1204:
1122:
1079:
619:
436:
36:
1225:
Meindersma, G. Wytze; Maase, Matthias; De Haan, André B. (2007). "Ionic
Liquids".
1190:"Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids"
768:
1-Methylimidazole is prepared mainly by two routes industrially. The main one is
587:
310:
285:
908:
1-Methylimidazole alkylates to form dialkyl imidazolium salts. Depending on the
769:
669:
45:
579:
1378:
1234:
1155:
Grimmett, M. R., Imidazole and
Benzimidazole Synthesis; 1997 Academic Press,
1126:
1083:
489:
479:
247:
1273:
1257:
1330:
1312:
913:
789:
724:
845:
797:
627:
1071:
631:
603:
236:
909:
459:
267:
207:
1208:
1015:. The donor properties of 1-methylimidazole have been analyzed by the
639:
1016:
773:
756:
565:
1111:[By the Constitution of the Lophins and related compounds].
1108:
937:
separates as a separate liquid phase under the reaction conditions.
668:
Except where otherwise noted, data are given for materials in their
23:
849:
777:
721:
227:
1001:
1-methylimidazole (NMIz) as a ligand forms octahedral ions M(NMIz)
647:
143:
136:
1055:
Albert, A., Heterocyclic
Chemistry, 2nd ed.; 1968 Athlone Press,
793:
785:
583:
469:
297:
1109:"Ueber die Constitution des Lophins und verwandter Verbindungen"
187:
167:
126:
347:
929:
561:
844:
The compound can be synthesized on a laboratory scale by
1224:
1106:
1005:
with M = Fe, Co, Ni, and a square-planar ion Cu(NMIz)
557:
1376:
309:
918:1-butyl-3-methylimidazolium hexafluorophosphate
112:
1227:Ullmann's Encyclopedia of Industrial Chemistry
1114:Berichte der deutschen chemischen Gesellschaft
1075:Ullmann's Encyclopedia of Industrial Chemistry
643:
755:-methyl group, this particular derivative of
1220:
1218:
1187:
1350:
1188:Baird, Eldon E.; Dervan, Peter B. (1996).
635:
257:
215:
1320:
1215:
903:
329:
1197:Journal of the American Chemical Society
382:InChI=1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
392:InChI=1/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
358:
235:
1377:
1286:
494:198 °C (388 °F; 471 K)
248:
385:Key: MCTWTZJPVLRJOU-UHFFFAOYSA-N
195:
175:
1289:"Solvents and sustainable chemistry"
727:organic compound with the formula CH
484:−6 °C (21 °F; 267 K)
1065:
996:
395:Key: MCTWTZJPVLRJOU-UHFFFAOYAU
300:
13:
44:
35:
14:
1401:
780:. The second method involves the
1336:
1287:Welton, Tom (11 November 2015).
928:
676:
527:
522:
22:
1344:
1280:
1107:Bronislaw Radziszewski (1882).
891:
672:(at 25 °C , 100 kPa).
1251:
1181:
1165:
1149:
1133:
1100:
1049:
912:and the counteranion, various
1:
1365:10.1016/S0020-1693(00)92544-1
1042:
763:
7:
1030:
746:
31:
10:
1406:
666:
503:
498:
464:82.10 g/mol
429:
404:
369:
96:
79:
63:
58:
30:
21:
1235:10.1002/14356007.l14_l01
1127:10.1002/cber.18820150207
1084:10.1002/14356007.a13_661
574:Precautionary statements
1353:Inorganica Chimica Acta
1274:10.15227/orgsyn.079.023
1229:. Weinheim: Wiley-VCH.
1078:. Weinheim: Wiley-VCH.
1313:10.1098/rspa.2015.0502
904:Ionic liquid precursor
49:
40:
782:Radziszewski reaction
48:
39:
848:of imidazole at the
65:Preferred IUPAC name
1305:2015RSPSA.47150502W
792:, and a mixture of
157:Beilstein Reference
18:
1299:(2183): 20150502.
699:Infobox references
50:
41:
17:1-Methylimidazole
16:
1261:Organic Syntheses
1244:978-3-527-30673-2
1209:10.1021/ja960720z
1037:4-Methylimidazole
711:1-Methylimidazole
707:Chemical compound
705:
704:
655:Safety data sheet
552:Hazard statements
343:CompTox Dashboard
145:Interactive image
138:Interactive image
87:-Methylimidazole
82:1-Methylimidazole
54:
53:
1397:
1369:
1368:
1348:
1342:
1341:
1340:
1334:
1324:
1284:
1278:
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1255:
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1212:
1194:
1185:
1179:
1169:
1163:
1153:
1147:
1137:
1131:
1130:
1121:(2): 1493–1496.
1104:
1098:
1097:
1069:
1063:
1053:
997:Donor properties
932:
910:alkylating agent
718:-methylimidazole
689:
683:
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437:Chemical formula
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351:
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313:
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286:Gmelin Reference
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867:
863:
859:
839:
835:
831:
827:
823:
819:
815:
811:
807:
772:methylation of
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749:
742:
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734:
730:
708:
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696:
695:
694: ?)
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5:
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1343:
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1250:
1243:
1214:
1203:(26): 6141–6.
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1148:
1132:
1099:
1093:978-3527306732
1092:
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770:acid-catalysed
765:
762:
748:
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732:
728:
706:
703:
702:
697:
675:
674:
670:standard state
667:
664:
663:
658:
651:
650:
616:P305+P351+P338
608:P303+P361+P353
600:P301+P330+P331
577:
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568:
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1178:
1177:3-540-65252-3
1174:
1168:
1162:
1161:0-12-303190-7
1158:
1152:
1146:
1145:0-582-06420-1
1142:
1136:
1128:
1124:
1120:
1117:(in German).
1116:
1115:
1110:
1103:
1095:
1089:
1085:
1081:
1077:
1076:
1068:
1062:
1061:0-485-11092-X
1058:
1052:
1048:
1038:
1035:
1034:
1028:
1018:
1014:
973:OH → 2 Cl + C
940:
939:
938:
931:
927:
926:
925:
919:
916:result, e.g.
915:
914:ionic liquids
911:
901:
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870:
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502:
497:
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490:Boiling point
488:
487:
483:
481:
480:Melting point
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360:DTXSID6052291
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249:ECHA InfoCard
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29:
25:
20:
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1346:
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1292:
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1253:
1226:
1200:
1196:
1183:
1167:
1151:
1135:
1118:
1112:
1102:
1073:
1067:
1051:
1023:= 1.16 and C
1000:
935:
907:
898:
895:
892:Applications
871:I + NaOH → H
864:N(NH)CH + CH
843:
790:formaldehyde
767:
752:
750:
725:heterocyclic
715:
714:
710:
709:
543:
505:
177:CHEBI:113454
97:Identifiers
89:
84:
80:Other names
70:
1359:: 517–522.
846:methylation
836:)CH + 3 H
798:methylamine
661:Oxford MSDS
538:Signal word
430:Properties
255:100.009.532
1385:Imidazoles
1379:Categories
1043:References
1019:yielding E
517:Pictograms
474:1.03 g/cm
460:Molar mass
416:n1ccn(c1)C
331:P4617QS63Y
208:ChemSpider
125:3D model (
104:CAS Number
73:-imidazole
69:1-Methyl-1
1017:ECW model
774:imidazole
764:Synthesis
757:imidazole
751:With the
612:P304+P340
604:P302+P352
596:P301+P312
508:labelling
276:210-484-7
268:EC Number
197:ChEMBL543
1390:Solvents
1331:26730217
1031:See also
1027:= 4.92.
920:("BMIMPF
850:pyridine
812:O + CH
778:methanol
747:Basicity
722:aromatic
499:Hazards
421:Cn1ccnc1
228:DrugBank
114:616-47-7
1322:4685879
1301:Bibcode
1268:: 236.
887:O + NaI
883:)CH + H
794:ammonia
786:glyoxal
692:what is
690: (
470:Density
454:
298:PubChem
237:DB02671
162:105197
1329:
1319:
1241:
1175:
1159:
1143:
1090:
1059:
720:is an
687:verify
684:
657:(SDS)
544:Danger
409:SMILES
188:ChEMBL
59:Names
1193:(PDF)
965:+ 2 C
941:2 MeC
879:N(NCH
868:I → I
832:N(NCH
824:→ H
820:+ NH
808:+ CH
804:(CHO)
784:from
374:InChI
291:2403
168:ChEBI
127:JSmol
1327:PMID
1239:ISBN
1173:ISBN
1157:ISBN
1141:ISBN
1088:ISBN
1057:ISBN
981:P(OC
924:"):
796:and
648:P501
644:P405
640:P363
636:P330
632:P322
628:P321
624:P312
620:P310
592:P280
588:P270
584:P264
580:P260
566:H314
562:H312
558:H302
322:UNII
311:1390
217:1348
1361:doi
1317:PMC
1309:doi
1297:471
1270:doi
1231:doi
1205:doi
1201:118
1123:doi
1080:doi
961:PCl
953:+ C
776:by
713:or
506:GHS
348:EPA
301:CID
90:NMI
1381::
1355:.
1325:.
1315:.
1307:.
1295:.
1291:.
1266:79
1264:.
1237:.
1217:^
1199:.
1195:.
1119:15
1086:.
816:NH
800:.
788:,
646:,
642:,
638:,
634:,
630:,
626:,
622:,
618:,
614:,
610:,
606:,
602:,
598:,
594:,
590:,
586:,
582:,
564:,
560:,
510::
1367:.
1363::
1357:3
1333:.
1311::
1303::
1277:.
1272::
1247:.
1233::
1211:.
1207::
1129:.
1125::
1096:.
1082::
1025:B
1021:B
1012:2
1007:4
1003:6
991:2
989:)
987:5
985:H
983:2
979:5
977:H
975:6
971:5
969:H
967:2
963:2
959:5
957:H
955:6
951:3
949:H
947:2
945:N
943:3
922:6
885:2
881:3
877:2
875:C
873:2
866:3
862:2
860:C
858:2
856:H
840:O
838:2
834:3
830:2
828:C
826:2
822:3
818:2
814:3
810:2
806:2
753:N
741:2
739:N
737:3
735:H
733:3
731:C
729:3
716:N
682:Y
452:2
450:N
448:6
446:H
444:4
442:C
350:)
346:(
129:)
85:N
71:H
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