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Dimethyl acetylenedicarboxylate

Acetylenedicarboxylic acid dimethyl ester organic solvents Hexafluoro-2-butyne, Acetylene

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. 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. The acid is then esterified with methanol, using sulfuric acid as a catalyst:

:[[File:Preparation_of_dimethyl_acetylenedicarboxylate.png|450px]]

Safety

DMAD is a lachrymator and a vesicant.

References

References

  1. Stelmach, J. E.; Winkler, J. D. "Dimethyl Acetylenedicarboxylate"in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi. 10.1002/047084289X.
  2. (2007). "Dimethyl Acetylene Dicarboxylate". Synlett.
  3. (1877). "Ueber Acetylendicarbonsäure". Berichte der Deutschen Chemischen Gesellschaft.
  4. Abbott, T. W.. (1938). "Acetylenedicarboxylic acid". Organic Syntheses.
  5. Huntress, E. H.. (1952). "Dimethyl Acetylenedicarboxylate". Organic Syntheses.
  6. Klain, G. (May 1988). "Metabolic alterations induced by topical dimethylacetylenedicarboxylate*1". Fundamental and Applied Toxicology.
  7. Slovak, A. J. M.. (June 1984). "Delayed dermal burns caused by dimethyl acetylenedicarboxylate". Contact Dermatitis.
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alkyne-derivatives methyl-esters carboxylate-esters blister-agents lachrymatory-agents
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