D138401
Dimethyl acetylenedicarboxylate
95%
Synonym(s):
Dimethyl 2-butynedioate
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About This Item
Linear Formula:
CH3OCOC≡CCO2CH3
CAS Number:
Molecular Weight:
142.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-098-4
Beilstein/REAXYS Number:
607063
MDL number:
Assay:
95%
Form:
liquid
InChI key
VHILMKFSCRWWIJ-UHFFFAOYSA-N
InChI
1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
SMILES string
COC(=O)C#CC(=O)OC
assay
95%
form
liquid
Quality Level
bp
95-98 °C/19 mmHg (lit.)
density
1.156 g/mL at 25 °C (lit.)
Related Categories
General description
Dimethyl acetylenedicarboxylate (DMAD) is an ester utilized as a dienophile and a dipolarophile in cycloaddition reactions.
Application
Versatile dienophile used in Diels-Alder reactions.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
186.8 °F - closed cup
flash_point_c
86 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Steven E Wheeler et al.
Journal of the American Chemical Society, 132(10), 3304-3311 (2010-02-18)
Stereoselective Diels-Alder cycloadditions that probe substituent effects in aryl-aryl sandwich complexes were studied experimentally and theoretically. Computations on model systems demonstrate that the stereoselectivity in these reactions is mediated by differential pi-stacking interactions in competing transition states. This allows relative
Dimethyl acetylenedicarboxylate: A versatile tool in organic synthesis
CG Neochoritis, et al.
Synthesis, 537-585 (2014)
Yi Li et al.
Polymers, 13(3) (2021-01-28)
Big spherulite structure and high crystallinity are the two main drawbacks of poly(butylene succinate) (PBS) and hinder its application. In this work, a new type of copolyester poly(butylene succinate-co-butylene acetylenedicarboxylate) (PBSAD) is synthesized. With the incorporation of acetylenedicarboxylate (AD) units
Yuanyuan Chen et al.
Journal of the American Chemical Society, 129(35), 10773-10784 (2007-08-19)
Recently, it was reported that both dienylfurans and dienylisobenzofurans could react with dimethyl acetylenedicarboxylate (DMAD) to give [8+2] cycloadducts. Understanding these [8+2] reactions will aid the design of additional [8+2] reactions, which have the potential for the synthesis of 10-membered
Qiuping Ding et al.
The Journal of organic chemistry, 74(2), 921-924 (2008-12-06)
Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoximes, DMAD, and bromine are described, which afford the unexpected isoquinoline-based azomethine ylides in good to excellent yields. The products could be further elaborated via palladium-catalyzed cross-coupling reactions to generate highly functionalized isoquinoline-based stable
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