Benzal chloride

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Benzal chloride
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 98-87-3
PubChem 24855098
ChemSpider 7133
RTECS number CZ5075000
style="background: #F8EABA; text-align: center;" colspan="2" | 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)
style="background: #F8EABA; text-align: center;" colspan="2" | 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 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.

References

  1. "BENZAL CHLORIDE". International Programme on Chemical Safety. Retrieved 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.
de:Benzalchlorid

es:Cloruro de bencilideno fr:(dichlorométhyl)benzène nl:Benzalchloride