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Dimethyl acetylenedicarboxylate



Dimethyl acetylenedicarboxylate
IUPAC name Dimethyl
acetylenedicarboxylate
Other names DMAD
Acetylenedicarboxylic
acid, dimethyl ester
Identifiers
CAS number 762-42-5
RTECS number ES0175000
SMILES O=C(OC)C#CC(OC)=O
Properties
Molecular formula C6H6O4
Molar mass 142.11 g/mol
Appearance Colorless liquid
Density 1.1564 g/cm³
Melting point

-117 °C

Boiling point

195–198 °C
96–98° at 8 mm Hg

Solubility in water Insoluble
Solubility in other solvents Soluble in most
organic solvents
Refractive index (nD) 1.447
Structure
Dipole moment 0 D
Hazards
Main hazards Toxic gas
R-phrases R34
S-phrases S23 S26 S27
S36/37/39 S45
Flash point 187 °F
Related Compounds
Related compounds Methyl propiolate,
Hexafluoro-2-butyne,
Acetylene
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dimethyl acetylenedicarboxylate (DMAD) is the organic compound with the formula CH3O2CC2CO2CH3. This alkyne, which exists as a liquid at room temperature, is highly electrophilic. As such, DMAD, as it is commonly called in the laboratory, is widely employed as a dienophile in cycloaddition reactions, such as the Diels-Alder reaction. It is also a potent Michael acceptor.[1][2]

Additional recommended knowledge

Preparation

Although inexpensively available, DMAD is prepared today as it was originally.[3] Maleic acid is brominated and the resulting dibromosuccinic acid is dehydrohalogenated.[4] The dicarboxylic acid is then esterified with methanol and sulfuric acid as a catalyst.[5]

Safety

DMAD is a lachrymator and a vesicant.

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: 10.1002/047084289.
  2. ^ Sahoo, Manoj Kumar: Dimethyl Acetylene Dicarboxylate SYNLETT 2007, No. 13, pp 2142–2143 doi:10.1055/s-2007-984894 Open access
  3. ^ Bandrowski, E. “Ueber Acetylendicarbonsäure” Chemische Berichte band 10, 838 (1877).
  4. ^ Abbott, T. W.; Arnold, R. T.; Thompson, R. B. “Acetylenedicarboxyltic acid” Organic Syntheses, Collective Volume 2, page 10.
  5. ^ Huntress, E. H. Lesslie, T. E.; Bornstein, J. “Dimethyl Acetylenedicarboxylate” Organic Syntheses, Collective Volume 4, page 329.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dimethyl_acetylenedicarboxylate". A list of authors is available in Wikipedia.
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