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24:
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617:
709:
609:
864:
Stelmach, J. E.; Winkler, J. D. "Dimethyl
Acetylenedicarboxylate"in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
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109:
179:
775:. This compound exists as a colorless liquid at room temperature. This compound was used in the preparation of
605:
533:
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129:
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621:
45:
23:
804:
800:
673:
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276:
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759:
in which the ester groups are conjugated with a C-C triple bond. As such, the molecule is highly
585:
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450:
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353:
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149:
85:
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987:
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792:
788:
648:
787:
Although inexpensively available, DMAD is prepared today as it was originally.
419:
195 to 198 °C (383 to 388 °F; 468 to 471 K) (96–98° at 8 mm Hg)
932:
776:
764:
436:
376:
140:
1005:
965:
678:
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883:
845:
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394:
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Except where otherwise noted, data are given for materials in their
567:
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222:
108:
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637:
629:
264:
986:
Huntress, E. H.; Lesslie, T. E.; Bornstein, J. (1952).
704:
946:
Abbott, T. W.; Arnold, R. T.; Thompson, R. B. (1938).
210:
84:
921:Berichte der Deutschen Chemischen Gesellschaft
8:
304:InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
314:InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
279:
170:
148:
15:
899:
246:
767:in cycloaddition reactions, such as the
857:
335:
300:
275:
653:187 °C (369 °F; 460 K)
161:
307:Key: VHILMKFSCRWWIJ-UHFFFAOYSA-N
128:
7:
409:−18 °C (0 °F; 255 K)
317:Key: VHILMKFSCRWWIJ-UHFFFAOYAX
201:
884:"Dimethyl Acetylene Dicarboxylate"
14:
988:"Dimethyl Acetylenedicarboxylate"
827:
694:
537:
532:
31:
22:
17:Dimethyl acetylenedicarboxylate
729:Dimethyl acetylenedicarboxylate
690:(at 25 °C , 100 kPa).
763:, and is widely employed as a
496:Occupational safety and health
1:
917:"Ueber Acetylendicarbonsäure"
948:"Acetylenedicarboxylic acid"
1059:
1014:, vol. 4, p. 329
809:acetylenedicarboxylic acid
381:142.11 g/mol
974:, vol. 2, p. 10
933:10.1002/cber.187701001231
795:and the resulting dibromo
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346:
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68:
56:
44:
39:
30:
21:
1006:10.15227/orgsyn.032.0055
966:10.15227/orgsyn.018.0003
580:Precautionary statements
50:Dimethyl but-2-ynedioate
915:Bandrowski, E. (1877).
771:. It is also a potent
901:10.1055/s-2007-984894
882:Sahoo, Manoj (2007).
61:Acetylenedicarboxylic
811:. The acid is then
769:Diels-Alder reaction
46:Preferred IUPAC name
805:potassium hydroxide
735:with the formula CH
674:Hexafluoro-2-butyne
426:Solubility in water
63:acid dimethyl ester
18:
1043:Carboxylate esters
1033:Alkyne derivatives
870:10.1002/047084289X
801:dehydrohalogenated
717:Infobox references
658:Related compounds
439:in other solvents
16:
1012:Collected Volumes
993:Organic Syntheses
972:Collected Volumes
953:Organic Syntheses
894:(13): 2142–2143.
725:Chemical compound
723:
722:
669:Methyl propiolate
664:Related compounds
562:Hazard statements
444:organic solvents
389:Colorless liquid
338:COC(=O)C#CC(=O)OC
260:CompTox Dashboard
110:Interactive image
1050:
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831:
773:Michael acceptor
733:organic compound
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451:Refractive index
354:Chemical formula
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823:as a catalyst:
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712: ?)
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442:Soluble in most
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688:standard state
685:
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660:
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645:
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618:P305+P351+P338
610:P303+P361+P353
606:P301+P330+P331
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1038:Methyl esters
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825:
824:
822:
821:sulfuric acid
818:
814:
810:
806:
802:
798:
797:succinic acid
794:
790:
782:
780:
778:
774:
770:
766:
762:
761:electrophilic
758:
755:. It is a di-
734:
731:(DMAD) is an
730:
718:
711:
706:
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476:Dipole moment
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430:
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415:Boiling point
413:
412:
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405:Melting point
403:
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277:DTXSID0061088
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162:ECHA InfoCard
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139:
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130:ChEMBL3248452
127:
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55:
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20:
1011:
997:
991:
981:
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941:
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920:
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891:
887:
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860:
839:
786:
728:
727:
553:
515:
505:Main hazards
494:
454:
399:1.1564 g/cm
223:RTECS number
69:Identifiers
57:Other names
927:: 838–842.
842:lachrymator
789:Maleic acid
783:Preparation
649:Flash point
548:Signal word
499:(OHS/OSH):
386:Appearance
347:Properties
168:100.010.999
1027:Categories
852:References
840:DMAD is a
813:esterified
793:brominated
777:nedocromil
765:dienophile
527:Pictograms
469:Structure
437:Solubility
431:Insoluble
377:Molar mass
248:7HZA2PL15F
141:ChemSpider
97:3D model (
76:CAS Number
807:yielding
679:Acetylene
614:P304+P340
602:P301+P312
518:labelling
230:ES0175000
189:212-098-4
181:EC Number
846:vesicant
817:methanol
489:Hazards
86:762-42-5
888:Synlett
710:what is
708: (
395:Density
371:
199:PubChem
1000:: 55.
844:and a
836:Safety
705:verify
702:
554:Danger
509:Toxic
464:1.447
331:SMILES
121:ChEMBL
40:Names
960:: 3.
815:with
803:with
757:ester
296:InChI
212:12980
150:12440
99:JSmol
892:2007
819:and
642:P501
638:P405
634:P363
630:P330
626:P321
622:P310
598:P280
594:P270
590:P264
586:P260
572:H314
568:H302
239:UNII
59:DMAD
1002:doi
962:doi
929:doi
896:doi
866:doi
799:is
791:is
516:GHS
265:EPA
202:CID
1029::
1009:;
998:32
996:.
990:.
969:;
958:18
956:.
950:.
925:10
923:.
919:.
890:.
886:.
848:.
779:.
751:CH
747:CO
743:CC
640:,
636:,
632:,
628:,
624:,
620:,
616:,
612:,
608:,
604:,
600:,
596:,
592:,
588:,
570:,
520::
481:0
1016:.
1004::
976:.
964::
935:.
931::
904:.
898::
872:.
868::
753:3
749:2
745:2
741:2
739:O
737:3
700:Y
676:,
671:,
483:D
460:)
458:D
455:n
453:(
369:4
367:O
365:6
363:H
361:6
359:C
267:)
263:(
101:)
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