Benzal chloride

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Benzal chloride
IUPAC name	Dichloromethylbenzene
Other names	Benzal chloride α,α-Dichlorobenzenea benzylidene chloride benzyl dichloride
Identifiers
CAS number	[98-87-3]
PubChem	24855098
RTECS number	CZ5075000
Properties
Molecular formula	C7H6Cl2
Molar mass	161.03 g/mol
Appearance	Colorless liquid
Density	1.254 g/cm3, liquid
Melting point	−17 to −15 °C
Boiling point	205 °C (82 °C @10 mm Hg)
Solubility in water	low
Vapor pressure	0.6 kPa (45 °C)
Hazards
EU classification	Toxic (T), Carc. Cat. 2B, Dangerous for the environment (N)
R-phrases	22-23-37/38-40-41
S-phrases	36/37-38-45
Flash point	93 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Benzal chloride is an organic compound with the formula C₆H₅CHCl₂.^[1] 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:^[2]

C₆H₅CHCl₂ + H₂O → C₆H₅CHO + 2 HCl

Addition of strong base to benzal chloride generates phenylcarbene.

[edit] References

1. ^ BENZAL CHLORIDE. International Programme on Chemical Safety. Retrieved on 2007-10-30.
2. ^ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.