207:
114:
376:
24:
371:
366:
643:
384:
346:
759:
Lee, Hong Myung; Nieto-Oberhuber, Cristina; Shair, Matthew D. (2008-12-17). "Enantioselective
Synthesis of (+)-Cortistatin A, a Potent and Selective Inhibitor of Endothelial Cell Proliferation".
502:
494:
246:
839:
498:
810:
Amano, Seiji; Takemura, Noriaki; Ohtsuka, Masami; Ogawa, Seiichiro; Chida, Noritaka (1999-03-26). "Total synthesis of paniculide A from d-glucose".
856:
438:
881:
221:
628:. MEM protecting groups are generally preferred to methoxymethyl (MOM) protecting groups, both in terms of formation and removal.
716:
732:
Corey, E. J.; Gras, Jean-Louis; Ulrich, Peter (1976-03-01). "A new general method for protection of the hydroxyl function".
482:
428:
164:
375:
185:
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121:
871:
450:
681:
530:
365:
470:
434:
109:
458:
398:
358:
837:
bis(Chloromethyl) Ether and
Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2
474:
202:
37:
526:
486:
446:
792:
649:
The MEM protecting group can be cleaved (deprotection) with a range of Lewis and
Bronsted acids.
542:
522:
462:
478:
23:
784:
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712:
613:
605:
819:
768:
741:
704:
631:
Typically, the alcohol to be protected is deprotonated with a non-nucleophilic base such as
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173:
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113:
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559:
823:
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796:
331:
102:
550:
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300:
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416:
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788:
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321:
140:
122:
772:
412:
558:
Except where otherwise noted, data are given for materials in their
408:
642:
641:
70:
60:
546:
699:
Wuts, Peter G. M. (2001). "2-Methoxyethoxymethyl
Chloride".
518:
190:
639:
followed by addition of 2-methoxyethoxymethyl chloride.
336:
50–52 °C (122–126 °F; 323–325 K) 13 mm Hg
152:
46:
701:Encyclopedia of Reagents for Organic Synthesis
604:. A colorless liquid, it is classified as a
8:
230:InChI=1S/C4H9ClO2/c1-6-2-3-7-4-5/h2-4H2,1H3
205:
112:
90:
15:
172:
761:Journal of the American Chemical Society
599:
595:
591:
587:
840:Report on carcinogens, eleventh edition
673:
251:
226:
201:
103:
233:Key: BIAAQBNMRITRDV-UHFFFAOYSA-N
7:
143:
14:
616:, it is used for introducing the
682:"2-Methoxyethoxymethyl chloride"
374:
369:
364:
287:
281:
22:
562:(at 25 °C , 100 kPa).
17:2-Methoxyethoxymethyl chloride
857:Reagents for organic chemistry
578:2-Methoxyethoxymethyl chloride
290:
275:
1:
824:10.1016/S0040-4020(99)00096-4
746:10.1016/S0040-4039(00)92890-9
898:
659:chloromethyl methyl ether
633:N,N-diisopropylethylamine
556:
345:
340:
262:
242:
217:
30:
21:
882:IARC Group 1 carcinogens
709:10.1002/047084289X.rm100
686:pubchem.ncbi.nlm.nih.gov
429:Precautionary statements
646:
645:
657:The closely related
608:. It is used as an
767:(50): 16864–16866.
734:Tetrahedron Letters
618:methoxyethoxy ether
308: g·mol
18:
647:
566:Infobox references
16:
867:Protecting groups
862:Alkylating agents
818:(13): 3855–3870.
773:10.1021/ja8071918
661:is a known human
614:organic synthesis
606:chloroalkyl ether
574:Chemical compound
572:
571:
399:Hazard statements
316:colorless liquid
186:CompTox Dashboard
72:Interactive image
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626:protecting group
610:alkylating agent
603:
582:organic compound
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270:Chemical formula
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50:
26:
19:
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872:Organochlorides
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740:(11): 809–812.
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637:dichloromethane
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5:
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569:
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560:standard state
557:
554:
553:
503:P305+P351+P338
495:P303+P361+P353
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13:
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2:
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821:
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803:
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766:
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755:
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747:
743:
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728:
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660:
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650:
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634:
629:
627:
623:
619:
615:
611:
607:
584:with formula
583:
579:
567:
561:
555:
433:
430:
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425:
403:
400:
396:
395:
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386:
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367:
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351:
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332:Boiling point
330:
329:
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323:
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304:
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203:DTXSID8063250
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104:ECHA InfoCard
101:
100:
93:
89:
88:
86:
84:
81:
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73:
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68:
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62:
57:
56:
49:
45:
44:
42:
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35:
34:
29:
25:
20:
836:
832:
815:
811:
805:
764:
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754:
737:
733:
727:
700:
694:
685:
676:
656:
648:
630:
621:
617:
577:
576:
390:
347:
31:Identifiers
812:Tetrahedron
635:(DIPEA) in
385:Signal word
326:1.094 g cm
313:Appearance
263:Properties
110:100.021.446
851:Categories
718:0471936235
669:References
663:carcinogen
359:Pictograms
301:Molar mass
174:A5RRM67QUG
83:ChemSpider
59:3D model (
38:CAS Number
797:207132632
781:0002-7863
543:P403+P235
539:P403+P233
535:P370+P378
531:P362+P364
527:P337+P317
523:P332+P317
499:P304+P340
491:P302+P352
487:P301+P317
471:P264+P265
350:labelling
131:223-589-8
123:EC Number
48:3970-21-6
789:19053422
341:Hazards
254:COCCOCCl
322:Density
141:PubChem
877:Ethers
795:
787:
779:
715:
653:Safety
580:is an
391:Danger
306:124.56
247:SMILES
793:S2CID
612:. In
222:InChI
154:77590
92:69995
61:JSmol
785:PMID
777:ISSN
713:ISBN
551:P501
547:P405
519:P330
515:P321
511:P319
507:P318
483:P280
479:P271
475:P270
467:P264
463:P261
459:P243
455:P242
451:P241
447:P240
443:P233
439:P210
435:P203
421:H335
417:H319
413:H315
409:H302
405:H226
165:UNII
820:doi
769:doi
765:130
742:doi
705:doi
665:.
622:MEM
598:OCH
590:OCH
348:GHS
191:EPA
144:CID
853::
816:55
814:.
791:.
783:.
775:.
763:.
738:17
736:.
711:.
703:.
684:.
624:)
602:Cl
594:CH
586:CH
549:,
545:,
541:,
537:,
533:,
529:,
525:,
521:,
517:,
513:,
509:,
505:,
501:,
497:,
493:,
489:,
485:,
481:,
477:,
473:,
469:,
465:,
461:,
457:,
453:,
449:,
445:,
441:,
437:,
419:,
415:,
411:,
407:,
352::
288:Cl
826:.
822::
799:.
771::
748:.
744::
721:.
707::
688:.
620:(
600:2
596:2
592:2
588:3
294:2
291:O
285:9
282:H
279:4
276:C
193:)
189:(
63:)
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