245:
152:
33:
470:
465:
24:
956:
Paine, John B. (1 July 2008). "Esters of
Pyromellitic Acid. Part I. Esters of Achiral Alcohols: Regioselective Synthesis of Partial and Mixed Pyromellitate Esters, Mechanism of Transesterification in the Quantitative Esterification of the Pyromellitate System Using Orthoformate Esters, and a Facile
908:
Liu, Hui; Tomooka, Craig S.; Xu, Simon L.; Yerxa, Benjamin R.; Sullivan, Robert W.; Xiong, Yifeng; Moore, Harold W. (1999). "Dimethyl
Squarate and ITS Conversion to 3-Ethenyl-4-Methoxycyclobutene-1,2-Dione and 2-Butyl-6-Ethenyl-5-Methoxy-1,4-Benzoquinone".
478:
445:
576:
883:
568:
281:
572:
998:
943:
524:
259:
812:
can be driven closer to completion by employing trimethyl orthoformate to convert water byproduct to methanol and
641:
798:
518:
202:
147:
223:
560:
748:
469:
109:
159:
604:
240:
464:
1008:
825:
778:
to form R-NH-CHO, which can undergo further reactions. It is used in the production of some
536:
492:
457:
592:
1003:
759:
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and
588:
211:
45:
580:
129:
8:
846:
808:
to their corresponding methyl esters. Alternatively, acid-catalyzed esterifications with
85:
75:
244:
151:
791:
544:
974:
939:
760:
697:
681:
966:
918:
859:
840:
744:
713:
696:. In general cases, these acetals can be deprotected back to the aldehyde by using
661:
421:
304:
32:
854:
805:
787:
191:
532:
834:
813:
635:
608:
548:
410:
804:
Trimethyl orthoformate is also an effective reagent for converting compatible
992:
922:
887:
863:
772:
556:
403:
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140:
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764:
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332:
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970:
739:
Trimethyl orthoformate can also be prepared from the reaction between
779:
957:
Synthesis of the Ortho
Pyromellitate Diester Substitution Pattern".
634:
Except where otherwise noted, data are given for materials in their
23:
938:
Ashford's
Dictionary of Industrial Chemicals, Third edition, 2011,
809:
689:
616:
108:
708:
Trimethyl orthoformate is prepared on an industrial scale by the
677:
552:
399:
363:
178:
498:
693:
510:
596:
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528:
228:
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786:
and picoxystrobin), as well as for some members of the
502:
907:
828:(triethoxymethane), another trialkyl orthoformate
990:
190:
84:
612:
388:100.6 °C (213.1 °F; 373.8 K)
801:are also made from trimethyl orthoformate.
243:
150:
128:
934:
932:
672:. A colorless liquid, it is the simplest
268:InChI=1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3
210:
239:
991:
929:
378:−53 °C (−63 °F; 220 K)
141:
955:
59:2-Methoxyacetaldehyde dimethyl acetal
628:13 °C (55 °F; 286 K)
181:
13:
692:with trimethyl orthoformate is an
14:
1020:
959:The Journal of Organic Chemistry
688:. The product of reaction of an
468:
463:
316:
31:
22:
638:(at 25 °C , 100 kPa).
999:Reagents for organic chemistry
949:
901:
892:
877:
322:
310:
1:
870:
849:(tetramethyl orthocarbonate)
799:pharmaceutical intermediates
703:
7:
819:
10:
1025:
749:Williamson ether synthesis
763:systems. It introduces a
632:
444:
439:
297:
277:
255:
68:
56:
44:
39:
30:
21:
923:10.15227/orgsyn.076.0189
519:Precautionary statements
664:with the formula HC(OCH
17:Trimethyl orthoformate
884:Trimethyl orthoformate
831:Other methoxymethanes
754:
654:Trimethyl orthoformate
826:Triethyl orthoformate
684:for the formation of
747:, an example of the
46:Preferred IUPAC name
847:Tetramethoxymethane
792:antibacterial drugs
340: g·mol
63:Methyl orthoformate
18:
862:, heavier analog,
642:Infobox references
16:
971:10.1021/jo800543w
965:(13): 4929–4938.
944:978-0-9522674-3-0
911:Organic Syntheses
761:heterocyclic ring
698:hydrochloric acid
682:organic synthesis
650:Chemical compound
648:
647:
493:Hazard statements
348:Colorless liquid
224:CompTox Dashboard
110:Interactive image
50:Trimethoxymethane
1016:
983:
982:
953:
947:
936:
927:
926:
905:
899:
896:
890:
881:
860:Trimethoxysilane
841:Dimethoxymethane
837:(dimethyl ether)
806:carboxylic acids
771:substrate, e.g.
745:sodium methoxide
714:hydrogen cyanide
662:organic compound
618:
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422:Refractive index
339:
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305:Chemical formula
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35:
26:
19:
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855:Pinner reaction
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61:Methoxymethylal
60:
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51:
12:
11:
5:
1022:
1012:
1011:
1006:
1001:
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928:
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898:Alfa Aesar SDS
891:
875:
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851:
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844:
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835:Methoxymethane
829:
821:
818:
814:methyl formate
782:(for example:
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733:
729:
725:
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669:
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636:standard state
633:
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619:
577:P305+P351+P338
569:P303+P361+P353
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415:1 kPa at 7 °C
413:
411:Vapor pressure
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9:
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3:
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1021:
1010:
1009:Methyl esters
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1005:
1002:
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994:
980:
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916:
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904:
895:
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888:Sigma-Aldrich
885:
880:
876:
865:
864:isoelectronic
861:
858:
856:
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830:
827:
824:
823:
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811:
807:
802:
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795:
793:
789:
785:
781:
777:
770:
766:
762:
752:
750:
746:
742:
720:HCN + 3 HOCH
719:
718:
717:
715:
711:
701:
699:
695:
691:
687:
686:methyl ethers
683:
679:
675:
663:
659:
655:
643:
637:
631:
627:
625:
622:
621:
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450:
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438:
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427:
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419:
418:
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409:
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404:diethyl ether
401:
397:
395:
392:
391:
387:
385:
384:Boiling point
382:
381:
377:
375:
374:Melting point
372:
371:
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241:DTXSID7027122
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142:ECHA InfoCard
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55:
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38:
34:
29:
25:
20:
962:
958:
951:
914:
910:
903:
894:
879:
803:
797:A number of
796:
784:azoxystrobin
769:nucleophilic
765:formyl group
758:
738:
710:methanolysis
707:
657:
653:
652:
484:
446:
425:
368:0.9676 g/cm
69:Identifiers
57:Other names
1004:Orthoesters
946:, page 9388
624:Flash point
479:Signal word
398:soluble in
345:Appearance
298:Properties
289:O(C)C(OC)OC
148:100.005.224
993:Categories
871:References
843:(methylal)
790:family of
780:fungicides
741:chloroform
676:. It is a
674:orthoester
458:Pictograms
394:Solubility
333:Molar mass
212:XAM28819YJ
121:ChemSpider
97:3D model (
76:CAS Number
724:→ HC(OCH
704:Synthesis
660:) is the
609:P403+P235
605:P403+P233
601:P370+P378
593:P337+P313
589:P332+P313
573:P304+P340
565:P302+P352
449:labelling
169:205-745-7
161:EC Number
979:18522420
866:compound
820:See also
810:methanol
788:floxacin
690:aldehyde
680:used in
440:Hazards
358:pungent
86:149-73-5
917:: 189.
678:reagent
435:1.3773
400:ethanol
364:Density
338:106.121
179:PubChem
977:
942:
694:acetal
485:Danger
282:SMILES
40:Names
767:to a
732:+ NH
260:InChI
99:JSmol
975:PMID
940:ISBN
743:and
658:TMOF
617:P501
613:P405
597:P362
585:P321
581:P312
561:P280
557:P271
553:P264
549:P261
545:P243
541:P242
537:P241
533:P240
529:P233
525:P210
511:H335
507:H319
503:H315
499:H225
354:Odor
203:UNII
192:9005
130:8655
967:doi
919:doi
886:at
773:RNH
755:Use
712:of
447:GHS
229:EPA
182:CID
995::
973:.
963:73
961:.
931:^
915:76
913:.
816:.
794:.
751:.
716::
700:.
615:,
611:,
607:,
603:,
599:,
595:,
591:,
587:,
583:,
579:,
575:,
571:,
567:,
563:,
559:,
555:,
551:,
547:,
543:,
539:,
535:,
531:,
527:,
509:,
505:,
501:,
451::
402:,
320:10
981:.
969::
925:.
921::
775:2
734:3
730:3
728:)
726:3
722:3
670:3
668:)
666:3
656:(
431:)
429:D
426:n
424:(
326:3
323:O
317:H
314:4
311:C
231:)
227:(
101:)
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