Dimethyl acetylenedicarboxylate
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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)
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PubChem CID
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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)
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1.447 |
| Structure | |
| 0 D | |
| Hazards | |
| Flash point | 187 °C (369 °F; 460 K) |
| Related compounds | |
Related compounds
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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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Template:Chembox Footer/trackingTemplate:Short description
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.
Preparation
Although inexpensively available, DMAD is prepared today as it was originally. Maleic acid is brominated and the resulting dibromosuccinic acid is dehydrohalogenated with potassium hydroxide yielding acetylenedicarboxylic acid.[3][4] The acid is then esterified with methanol, using sulfuric acid as a catalyst:[5]
Safety
DMAD is a lachrymator and a vesicant.[6][7]
References
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- ^ Stelmach, J. E.; Winkler, J. D. "Dimethyl Acetylenedicarboxylate"in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. Script error: No such module "CS1 identifiers"..
- ^ Page Module:Citation/CS1/styles.css has no content.Sahoo, Manoj (2007). "Dimethyl Acetylene Dicarboxylate". Synlett. 2007 (13): 2142–2143. doi:10.1055/s-2007-984894.
- ^ Page Module:Citation/CS1/styles.css has no content.Bandrowski, E. (1877). "Ueber Acetylendicarbonsäure". Berichte der Deutschen Chemischen Gesellschaft. 10: 838–842. doi:10.1002/cber.187701001231.
- ^ Page Module:Citation/CS1/styles.css has no content.Abbott, T. W.; Arnold, R. T.; Thompson, R. B. (1938). "Acetylenedicarboxylic acid". Organic Syntheses. 18: 3. doi:10.15227/orgsyn.018.0003; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 2, p. 10.
- ^ Page Module:Citation/CS1/styles.css has no content.Huntress, E. H.; Lesslie, T. E.; Bornstein, J. (1952). "Dimethyl Acetylenedicarboxylate". Organic Syntheses. 32: 55. doi:10.15227/orgsyn.032.0055; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 4, p. 329.
- ^ Page Module:Citation/CS1/styles.css has no content.Klain, G (May 1988). "Metabolic alterations induced by topical dimethylacetylenedicarboxylate*1". Fundamental and Applied Toxicology. 10 (4): 730–735. doi:10.1016/0272-0590(88)90199-6.
- ^ Page Module:Citation/CS1/styles.css has no content.Slovak, A. J. M.; Payne, A. R. (June 1984). "Delayed dermal burns caused by dimethyl acetylenedicarboxylate". Contact Dermatitis. 11 (1): 29–30. doi:10.1111/j.1600-0536.1984.tb00166.x. ISSN 0105-1873.
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