4-Vinylbenzyl chloride

4-Vinylbenzyl chloride is an organic compound with the formula ClCH2C6H4CH=CH2. It is a bifunctional molecule, featuring both vinyl and a benzylic chloride functional groups. It is a colorless liquid that is typically stored with a stabilizer to suppress polymerization.

4-Vinylbenzyl chloride
Names
Preferred IUPAC name
1-(Chloromethyl)-4-ethenylbenzene
Other names
1-(Chloromethyl)-4-vinylbenzene
α-Chloromethylstyrene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.975
EC Number
  • 250-005-9
UNII
  • InChI=1S/C9H9Cl/c1-2-8-3-5-9(7-10)6-4-8/h2-6H,1,7H2
    Key: ZRZHXNCATOYMJH-UHFFFAOYSA-N
  • C=Cc1ccc(cc1)CCl
Properties
C9H9Cl
Molar mass 152.62
Appearance colorless liquid
Density 1.083
Boiling point 229 °C (444 °F; 502 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 alkylating agent
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In combination with styrene, vinylbenzyl chloride is used as a comonomer in the production of chloromethylated polystyrene.[1] It is produced by the chlorination of vinyltoluene. Often vinyltoluene consists of a mixture of 3- and 4-vinyl isomers, in which case the vinylbenzyl chloride will also be produced as a mixture of isomers.[2]

References
  1. Montheard, Jean Pierre; Jegat, Corinne; Camps, Marcel "Vinylbenzylchloride (chloromethylstyrene), polymers, and copolymers. Recent reactions and applications" Journal of Macromolecular Science, Reviews in Macromolecular Chemistry and Physics 1999, volume C39, pp. 135-174.
  2. Denis H. James; William M. Castor (2007), "Styrene", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 1, doi:10.1002/14356007.a25_329.pub2, ISBN 978-3527306732
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