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| Names | |
|---|---|
| Preferred IUPAC name Dimethyl but-2-ynedioate | |
| Other names DMAD Acetylenedicarboxylic acid dimethyl ester | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.010.999 |
| EC Number |
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| RTECS number |
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| UNII | |
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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 | |
| 0D | |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Dimethyl acetylenedicarboxylate (DMAD) is anorganic 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 highlyelectrophilic, and is widely employed as adienophile in cycloaddition reactions, such as theDiels-Alder reaction. It is also a potentMichael acceptor.[1][2] This compound exists as a colorless liquid at room temperature. This compound was used in the preparation ofnedocromil.
Although inexpensively available, DMAD is prepared today as it was originally.Maleic acid isbrominated and the resulting dibromosuccinic acid isdehydrohalogenated withpotassium hydroxide yieldingacetylenedicarboxylic acid.[3][4] The acid is thenesterified withmethanol, usingsulfuric acid as a catalyst:[5]
DMAD is alachrymator and avesicant.[6][7]
