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Dimethyl acetylenedicarboxylate
Chemical compound / From Wikipedia, the free encyclopedia
Dimethyl acetylenedicarboxylate (DMAD) is an organic compound with the formula CH3O2CC2CO2CH3. It is a di-ester in which the ester groups are conjugated with a C-C triple bond. As such, the molecule is highly electrophilic, and is widely employed as a dienophile in cycloaddition reactions, such as the Diels-Alder reaction. It is also a potent Michael acceptor.[1][2] This compound exists as a colorless liquid at room temperature. This compound was used in the preparation of nedocromil.
Quick Facts Names, Identifiers ...
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Names | |
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Preferred IUPAC name
Dimethyl but-2-ynedioate | |
Other names
DMAD Acetylenedicarboxylic acid dimethyl ester | |
Identifiers | |
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3D model (JSmol) |
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ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.010.999 ![]() |
EC Number |
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PubChem CID |
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RTECS number |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C6H6O4 | |
Molar mass | 142.11 g/mol |
Appearance | Colorless liquid |
Density | 1.1564 g/cm3 |
Melting point | −18 °C (0 °F; 255 K) |
Boiling point | 195 to 198 °C (383 to 388 °F; 468 to 471 K) (96–98° at 8 mm Hg) |
Insoluble | |
Solubility in other solvents | Soluble in most organic solvents |
Refractive index (nD) |
1.447 |
Structure | |
0 D | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
Toxic |
GHS labelling: | |
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Danger | |
H302, H314 | |
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501 | |
Flash point | 187 °C (369 °F; 460 K) |
Related compounds | |
Related compounds |
Methyl propiolate, Hexafluoro-2-butyne, Acetylene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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