N,N'-Methylenebisacrylamide

[1][2] Acrylamide reacts with an aqueous solution of formaldehyde in the presence of copper(I) chloride as a polymerization inhibitor and sulfuric acid as catalyst to form N,N′-methylenebisacrylamide with yields of 60 to 80%.

In aqueous media, acrylonitrile also reacts with formaldehyde to give crude N,N′-methylenebisacrylamide, which can be purified by recrystallization with acetone/water.

Nucleophiles such as alcohols, amines, or thiols add across the activated vinyl groups, giving mixtures of mono- and disubstituted products.

As a bifunctional electron-poor dienophile, MBA reacts with electron-rich dienes, such as cyclopentadiene, in Diels–Alder reactions, giving the corresponding norbornene adducts.

As a symmetric, unconjugated divinyl monomer, MBA can be used with suitable initiators in cyclopolymerizations to create linear, soluble polymers whose backbones are built from five- and seven-membered rings.

Skeletal formula of methylenebisacrylamide
Ball-and-stick model of the methylenebisacrylamide model