Benzal chloride

Benzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis.

Benzal chloride is produced by the free radical chlorination of toluene, being preceded in the process by benzyl chloride and followed by benzotrichloride
 * C6H5CH3 +  Cl2   →  C6H5CH2Cl +  HCl
 * C6H5CH2Cl +  Cl2   →  C6H5CHCl2  +  HCl
 * C6H5CHCl2 +  Cl2   →  C6H5CCl3  +  HCl

Most benzal chloride is hydrolysed to benzaldehyde:
 * C6H5CHCl2 +  H2O   →  C6H5CHO  +  2 HCl

Addition of strong base to benzal chloride generates phenylcarbene.