332:
211:
44:
530:
35:
525:
922:
520:
685:
681:
782:
684:
686:
1129:
Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (2009). "New
Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism".
702:
538:
1014:
etching solution that removes fluorine atoms from the surface, which get replaced by oxygen, hydrogen, and water. This physically etches the surface as well to prepare the surface for better adhesion.
500:
687:
695:
628:
795:
709:
1207:
981:
381:
636:
1053:
588:
790:
1102:
346:
764:
1068:
D. Berndt, D. Spahrbier, "Batteries" in
Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.
802:
985:
632:
574:
289:
206:
310:
620:
529:
1037:
584:
524:
218:
1192:
327:
973:
1227:
519:
1222:
188:
1034:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
600:
552:
512:
926:
298:
56:
644:
8:
1202:
942:
640:
128:
104:
94:
331:
210:
168:
1007:
608:
148:
1147:
1098:
1049:
977:
1232:
1139:
1090:
1069:
1041:
997:
858:
744:
484:
404:
17:
1198:
1,2-Dimethoxyethane - chemical product info: properties, production, applications.
566:
993:
989:
965:
954:
756:
262:
237:
1045:
596:
1001:
874:
773:
652:
612:
21:
1165:
1216:
1197:
1117:
1094:
1073:
961:
870:
616:
473:
463:
199:
624:
1151:
938:
708:
648:
43:
950:
721:
694:
960:
Dimethoxyethane is often used as a higher-boiling-point alternative to
701:
432:
219:
179:
1143:
34:
946:
921:
580:
772:
Except where otherwise noted, data are given for materials in their
854:
667:
1128:
660:
127:
850:
842:
760:
453:
249:
558:
969:
1084:
957:. In the laboratory, DME is used as a coordinating solvent.
846:
738:
273:
159:
117:
592:
315:
1085:
Siegfried
Rebsdat; Dieter Mayer (2000). "Ethylene Glycol".
1011:
604:
972:
for some metal cations. It is therefore often used in
869:
Monoglyme is produced industrially by the reaction of
916:
984:are typical application. It is also suitable for
1214:
562:
261:
683:
103:
1087:Ullmann's Encyclopedia of Industrial Chemistry
996:. Dimethoxyethane is also a good solvent for
853:, especially in batteries. Dimethoxyethane is
656:
1028:
1026:
1010:dissolved in dimethoxyethane is used as a
330:
328:DTXSID2027838 DTXSID0025286, DTXSID2027838
209:
187:
297:
1132:Journal of the American Chemical Society
1023:
920:
1203:International Chemical Safety Card 1568
1193:Clariant Glymes Homepage www.glymes.com
355:InChI=1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3
326:
1215:
968:. Dimethoxyethane acts as a bidentate
945:), dimethoxyethane is used as the low-
468:−58 °C (−72 °F; 215 K)
365:InChI=1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3
200:
478:85 °C (185 °F; 358 K)
358:Key: SPEUIVXLLWOEMJ-UHFFFAOYSA-N
167:
726:−2 °C (28 °F; 271 K)
368:Key: SPEUIVXLLWOEMJ-UHFFFAOYAV
252:
13:
917:Applications as solvent and ligand
679:
14:
1244:
1186:
780:
765:Diethylene glycol dimethyl ether
528:
523:
518:
416:
42:
33:
776:(at 25 °C , 100 kPa).
1158:
1122:
1111:
1078:
1062:
1038:The Royal Society of Chemistry
831:ethylene glycol dimethyl ether
422:
410:
76:Ethylene glycol dimethyl ether
70:Ethane-1,2-diyl dimethyl ether
1:
1017:
986:palladium-catalyzed reactions
949:component of the solvent for
864:
933:(dimethoxyethane)(3-hexyne).
7:
1046:10.1039/9781849733069-00648
10:
1249:
15:
1170:Weiser Industries USA Inc
770:
730:
499:
494:
397:
377:
342:
87:
67:
55:
50:
41:
32:
1095:10.1002/14356007.a10_101
1074:10.1002/14356007.a03_343
974:organometallic chemistry
575:Precautionary statements
16:Not to be confused with
1089:. Weinheim: Wiley-VCH.
934:
690:
1208:Chemical hazard links
1040:. 2014. p. 704.
937:Together with a high-
924:
689:
927:coordination complex
672:(fire diamond)
57:Preferred IUPAC name
943:propylene carbonate
835:dimethyl cellosolve
485:Solubility in water
440: g·mol
149:Beilstein Reference
82:Dimethyl cellosolve
61:1,2-Dimethoxyethane
29:
1008:Sodium naphthalide
982:hydride reductions
978:Grignard reactions
935:
849:that is used as a
841:, is a colorless,
803:Infobox references
731:Related compounds
691:
27:
1144:10.1021/ja8100837
1138:(15): 5370–5371.
1055:978-0-85404-182-4
955:lithium batteries
925:Structure of the
811:Chemical compound
809:
808:
752:Related compounds
553:Hazard statements
448:Colorless liquid
311:CompTox Dashboard
129:Interactive image
1240:
1181:
1180:
1178:
1176:
1166:"Tetra-Etch FAQ"
1162:
1156:
1155:
1126:
1120:
1115:
1109:
1108:
1082:
1076:
1066:
1060:
1059:
1030:
994:Stille couplings
990:Suzuki reactions
817:, also known as
793:
787:
784:
783:
745:Dimethoxymethane
711:
704:
697:
682:
662:
658:
654:
650:
646:
642:
638:
634:
630:
626:
622:
618:
614:
610:
606:
602:
598:
594:
590:
586:
582:
568:
564:
560:
532:
527:
522:
439:
424:
418:
412:
405:Chemical formula
335:
334:
319:
317:
301:
265:
254:
238:Gmelin Reference
221:
213:
202:
191:
171:
131:
107:
46:
37:
30:
28:Dimethoxyethane
26:
18:dimethoxymethane
1248:
1247:
1243:
1242:
1241:
1239:
1238:
1237:
1213:
1212:
1189:
1184:
1174:
1172:
1164:
1163:
1159:
1127:
1123:
1118:Dimethoxyethane
1116:
1112:
1105:
1083:
1079:
1067:
1063:
1056:
1032:
1031:
1024:
1020:
1002:polysaccharides
966:tetrahydrofuran
932:
919:
912:
908:
904:
900:
896:
892:
888:
884:
867:
827:dimethyl glycol
815:Dimethoxyethane
812:
805:
800:
799:
798: ?)
789:
785:
781:
777:
763:
759:
757:Ethylene glycol
753:
741:
716:
715:
714:
713:
706:
699:
692:
688:
680:
577:
555:
541:
515:
487:
437:
427:
421:
415:
407:
393:
390:
385:
384:
373:
370:
369:
366:
360:
359:
356:
350:
349:
338:
320:
313:
304:
284:
268:
255:
240:
231:
194:
174:
151:
134:
121:
110:
97:
83:
81:
80:Dimethyl glycol
79:
77:
75:
73:
71:
63:
62:
25:
12:
11:
5:
1246:
1236:
1235:
1230:
1228:Ether solvents
1225:
1211:
1210:
1205:
1200:
1195:
1188:
1187:External links
1185:
1183:
1182:
1157:
1121:
1110:
1103:
1077:
1061:
1054:
1021:
1019:
1016:
941:solvent (e.g.
930:
918:
915:
914:
913:
910:
906:
902:
898:
894:
890:
886:
882:
875:ethylene oxide
866:
863:
810:
807:
806:
801:
779:
778:
774:standard state
771:
768:
767:
754:
751:
748:
747:
742:
736:
733:
732:
728:
727:
724:
718:
717:
707:
700:
693:
678:
677:
676:
675:
673:
664:
663:
629:P303+P361+P353
578:
573:
570:
569:
556:
551:
548:
547:
542:
537:
534:
533:
516:
511:
508:
507:
497:
496:
492:
491:
488:
483:
480:
479:
476:
470:
469:
466:
460:
459:
456:
450:
449:
446:
442:
441:
435:
429:
428:
425:
419:
413:
408:
403:
400:
399:
395:
394:
392:
391:
388:
380:
379:
378:
375:
374:
372:
371:
367:
364:
363:
361:
357:
354:
353:
345:
344:
343:
340:
339:
337:
336:
323:
321:
309:
306:
305:
303:
302:
294:
292:
286:
285:
283:
282:
278:
276:
270:
269:
267:
266:
258:
256:
248:
245:
244:
241:
236:
233:
232:
230:
229:
225:
223:
215:
214:
204:
196:
195:
193:
192:
184:
182:
176:
175:
173:
172:
164:
162:
156:
155:
152:
147:
144:
143:
140:
139:Abbreviations
136:
135:
133:
132:
124:
122:
115:
112:
111:
109:
108:
100:
98:
93:
90:
89:
85:
84:
69:
65:
64:
60:
59:
53:
52:
48:
47:
39:
38:
22:dimethyl ether
9:
6:
4:
3:
2:
1245:
1234:
1231:
1229:
1226:
1224:
1223:Glycol ethers
1221:
1220:
1218:
1209:
1206:
1204:
1201:
1199:
1196:
1194:
1191:
1190:
1171:
1167:
1161:
1153:
1149:
1145:
1141:
1137:
1133:
1125:
1119:
1114:
1106:
1104:3-527-30673-0
1100:
1096:
1092:
1088:
1081:
1075:
1071:
1065:
1057:
1051:
1047:
1043:
1039:
1036:. Cambridge:
1035:
1029:
1027:
1022:
1015:
1013:
1009:
1005:
1003:
999:
995:
991:
987:
983:
979:
975:
971:
967:
963:
962:diethyl ether
958:
956:
952:
948:
944:
940:
928:
923:
880:
879:
878:
876:
872:
871:dimethylether
862:
860:
856:
852:
848:
845:, and liquid
844:
840:
836:
832:
828:
824:
820:
816:
804:
797:
792:
775:
769:
766:
762:
758:
755:
750:
749:
746:
743:
740:
735:
734:
729:
725:
723:
720:
719:
712:
705:
698:
674:
671:
670:
666:
665:
579:
576:
572:
571:
557:
554:
550:
549:
546:
543:
540:
536:
535:
531:
526:
521:
517:
514:
510:
509:
505:
503:
498:
493:
489:
486:
482:
481:
477:
475:
474:Boiling point
472:
471:
467:
465:
464:Melting point
462:
461:
457:
455:
452:
451:
447:
444:
443:
436:
434:
431:
430:
409:
406:
402:
401:
396:
387:
386:
383:
376:
362:
352:
351:
348:
341:
333:
329:
325:
324:
322:
312:
308:
307:
300:
296:
295:
293:
291:
288:
287:
280:
279:
277:
275:
272:
271:
264:
260:
259:
257:
251:
247:
246:
242:
239:
235:
234:
227:
226:
224:
222:
217:
216:
212:
208:
205:
203:
201:ECHA InfoCard
198:
197:
190:
186:
185:
183:
181:
178:
177:
170:
166:
165:
163:
161:
158:
157:
153:
150:
146:
145:
141:
138:
137:
130:
126:
125:
123:
119:
114:
113:
106:
102:
101:
99:
96:
92:
91:
86:
66:
58:
54:
49:
45:
40:
36:
31:
23:
19:
1173:. Retrieved
1169:
1160:
1135:
1131:
1124:
1113:
1086:
1080:
1064:
1033:
1006:
959:
951:electrolytes
939:permittivity
936:
868:
838:
834:
830:
826:
822:
818:
814:
813:
668:
544:
501:
458:0.8683 g/cm
274:RTECS number
88:Identifiers
68:Other names
761:1,4-Dioxane
722:Flash point
539:Signal word
445:Appearance
398:Properties
207:100.003.451
169:CHEBI:42263
1217:Categories
1018:References
988:including
865:Production
513:Pictograms
433:Molar mass
299:GXS24JF5IW
180:ChemSpider
116:3D model (
95:CAS Number
947:viscosity
823:monoglyme
653:P403+P235
649:P370+P378
641:P308+P313
637:P304+P340
633:P304+P312
504:labelling
490:miscible
281:KI1451000
228:203-794-9
220:EC Number
78:Monoglyme
1175:29 March
1152:20560633
855:miscible
737:Related
669:NFPA 704
495:Hazards
189:13854808
154:1209237
105:110-71-4
1233:Ligands
851:solvent
843:aprotic
796:what is
794: (
454:Density
250:PubChem
1150:
1101:
1052:
1000:- and
970:ligand
897:O → CH
837:, and
791:verify
788:
739:Ethers
567:H360FD
545:Danger
438:90.122
389:COCCOC
382:SMILES
51:Names
998:oligo
873:with
859:water
857:with
847:ether
819:glyme
347:InChI
243:1801
160:ChEBI
118:JSmol
74:Glyme
1177:2023
1148:PMID
1099:ISBN
1050:ISBN
1012:PTFE
992:and
980:and
964:and
929:NbCl
889:+ CH
661:P501
657:P405
645:P312
625:P281
621:P280
617:P271
613:P261
609:P243
605:P242
601:P241
597:P240
593:P233
589:P210
585:P202
581:P201
563:H332
559:H225
290:UNII
263:8071
142:DME
1140:doi
1136:131
1091:doi
1070:doi
1042:doi
953:of
909:OCH
901:OCH
885:OCH
839:DME
502:GHS
316:EPA
253:CID
72:DME
20:or
1219::
1168:.
1146:.
1134:.
1097:.
1048:.
1025:^
1004:.
976:.
905:CH
893:CH
881:CH
877::
861:.
833:,
829:,
825:,
821:,
659:,
655:,
651:,
647:,
643:,
639:,
635:,
631:,
627:,
623:,
619:,
615:,
611:,
607:,
603:,
599:,
595:,
591:,
587:,
583:,
565:,
561:,
506::
420:10
1179:.
1154:.
1142::
1107:.
1093::
1072::
1058:.
1044::
931:3
911:3
907:2
903:2
899:3
895:2
891:2
887:3
883:3
786:N
710:0
703:2
696:2
426:2
423:O
417:H
414:4
411:C
318:)
314:(
120:)
24:.
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