4-Chlorostyrene

Chemical properties

clear colourless to slightly yellow liquid. The side chain of p-chlorostyrene is a C=C double bond, so its chemical properties are more active. The compound can polymerize slowly at room temperature, and a polymerization inhibitor (stabilizer) can be added for storage.

The Uses of 4-Chlorostyrene

4-Chlorostyrene is used in the preparation of new bis(pyrazolyl)borato olefin complexes of copper(I). It is also employed in the investigation of regioselectivity in the cationic Heck reaction of 4-substituted styrenes. Further, it plays an important role in the preparation of 4-[(4-chloro-phenyl)-thioacetyl]-morpholine.

The Uses of 4-Chlorostyrene

4-Chlorostyrene was used in the following studies:
Study of chemical and biochemical properties of the vinyl group of styrene by the development of structure activity relationships (SAR).
Preparation of new bis(pyrazolyl)borato olefin complexes of copper(I).
To investigate the regioselectivity in the cationic Heck reaction of 4-substituted styrenes.

Preparation

Synthesis of 4-chlorostyrene: carry out catalytic dehydration reaction by 4-chlorophenethylalcohol at 280°C, the used catalyst is a modified aluminum silicate catalyst, and the yield is 80%.

Synthesis Reference(s)

p-Chlorostyrene is commercially produced as a monomer from p-chloroethylbenzene by an oxidation technique. It is also produced as a mixture with o-chlorostyrene.
Journal of the American Chemical Society, 69, p. 852, 1947 DOI: 10.1021/ja01196a033
Tetrahedron Letters, 31, p. 5061, 1990 DOI: 10.1016/S0040-4039(00)97806-7

General Description

4-Chlorostyrene is a para-halogenated styrene derivative. It undergoes graft copolymerization with acrylonitrile (AN) onto ethylene-propylene-diene terpolymer (EPDM) in the presence of benzoyl peroxide (initiator).