Dimethyl acetylenedicarboxylate

• DMAD
• 2- Butindisäuredimethylester
• Dimethylacetylenedicarboxylate

Slightly yellowish liquid

Liquid

1.16 g · cm -3 ( 20 ° C)

-18 ° C.

195-198 ° C

Insoluble in water

1,447

Risk

550 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Dimethyl acetylenedicarboxylate ( DMAD ) is an organic chemical compound with the formula C6H6O4 from the group consisting of alkynes, and carboxylic acid esters.

Production and representation

Maleic acid is brominated and the resulting dehydrohalogenated dibromosuccinic with potassium hydroxide. The resulting acetylene dicarboxylic acid is then esterified with methanol and sulfuric acid as a catalyst.

Properties

Dimethylacetylenedicarboxylate is a pale yellow liquid, which decomposes under severe heating or exposure to light.

Use

DMAD as a liquid at room temperature alkyne is highly electrophilic. Therefore, it is as a dienophile in cycloaddition reactions - used - such as the Diels- Alder reaction. There is also a strong Michael acceptor.

Safety

Dimethylacetylenedicarboxylate is an irritant and a Ätzstoff. Upon contact with metals hydrogen can evolve which may explode.