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List of IARC Group 2A Agents - Probably carcinogenic to humans
Benzal chloride
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Benzal chloride

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Benzal chloride
Skeletal formula of benzal chloride
Ball-and-stick model of benzal chloride
Names
Preferred IUPAC name
(Dichloromethyl)benzene
Other names
  • Benzyl dichloride
  • Benzylidene chloride
  • α,α-Dichlorotoluene
  • PhCl2H
Identifiers
3D model (JSmol)
1099407
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.463
EC Number
  • 249-854-8
KEGG
MeSH Compounds Benzylidene Compounds
PubChem CID
RTECS number
  • CZ5075000
UNII
UN number 1886 2810
  • InChI=1S/C7H6Cl2/c8-7(9)6-4-2-1-3-5-6/h1-5,7H checkY
    Key: CAHQGWAXKLQREW-UHFFFAOYSA-N checkY
  • ClC(Cl)c1ccccc1
  • C1=CC=C(C=C1)C(Cl)Cl
Properties
C7H6Cl2
Molar mass 161.03 g/mol
Appearance Colorless liquid
Density 1.254 g/cm3, liquid
Melting point −17 to −15 °C (1 to 5 °F; 256 to 258 K)
Boiling point 205 °C (401 °F; 478 K) (82 °C at 10 mmHg)
0.25 g/L at 39 °C
Vapor pressure 0.6 kPa (45 °C)
Hazards
GHS labelling:
GHS03: OxidizingGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H302, H315, H318, H331, H335, H351
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501
Flash point 93 °C (199 °F; 366 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

Preparation and usage

Benzal chloride is produced by the free radical chlorination of toluene, being preceded in the process by benzyl chloride (C6H5CH2Cl) and followed by benzotrichloride (C6H5CCl3):

C6H5CH3 + Cl2 → C6H5CH2Cl + HCl
C6H5CH2Cl + Cl2 → C6H5CHCl2 + HCl
C6H5CHCl2 + Cl2 → C6H5CCl3 + HCl

Benzylic halides are typically strong alkylating agents, and for this reason benzal chloride is treated as a hazardous compound.

Treatment of benzal chloride with sodium gives stilbene.

Most benzal chloride main industrial use is as a precursor to benzaldehyde. This conversion involves hydrolysis in the presence of base:

C6H5CHCl2 + H2O → C6H5CHO + 2 HCl

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