Dimethyl acetylenedicarboxylate

Dimethyl acetylenedicarboxylate

Chemical structure of DMAD
Ball-and-stick model
Names
IUPAC name Dimethyl but-2-ynedioate
Other names DMAD Acetylenedicarboxylic acid dimethyl ester
Identifiers
CAS Number	762-42-5 Y
ChemSpider	12440 Y
Jmol 3D model	Interactive image
RTECS number	ES0175000
InChI InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 Y Key: VHILMKFSCRWWIJ-UHFFFAOYSA-N Y InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 Key: VHILMKFSCRWWIJ-UHFFFAOYAX
SMILES COC(=O)C#CC(=O)OC
Properties
Chemical formula	C6H6O4
Molar mass	142.11 g/mol
Appearance	Colorless liquid
Density	1.1564 g/cm3
Melting point	c
Boiling point	195 to 198 °C (383 to 388 °F; 468 to 471 K) (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
Vapor pressure	{{{value}}}
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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Infobox references

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.

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 and sulfuric acid as a catalyst:

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Safety

DMAD is a lachrymator and a vesicant.