Benzal chloride

Benzal chloride

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ImageFileL1 = Benzal chloride.svg
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ImageFileR1 = Benzal chloride 3D.png ImageSizeR1 =
IUPACName = Dichloromethylbenzene
OtherNames = Benzal chloride α,α-Dichlorobenzenea benzylidene chloride benzyl dichloride
Section1 = Chembox Identifiers
CASNo = 98-87-3
EINECS =
PubChem = 24855098
SMILES =
InChI =
RTECS = CZ5075000
ChEBI =
KEGG =
Section2 = Chembox Properties
Formula = C7H6Cl2
MolarMass = 161.03 g/mol
Appearance = Colorless liquid
Density = 1.254 g/cm3, liquid
MeltingPt = −17 to −15 °C
BoilingPt = 205 °C (82 °C @10 mm Hg)
Solubility = low
LogP =
VaporPressure = 0.6 kPa (45 °C)
HenryConstant =
Section3 = Chembox Structure
CrystalStruct =
Coordination =
MolShape =
Section4 = Chembox Hazards
EUClass = Toxic (T), Carc. Cat. 2B, Dangerous for the environment (N)
MainHazards =
NFPA-H =
NFPA-F =
NFPA-R =
NFPA-O =
RPhrases = 22-23-37/38-40-41
SPhrases = 36/37-38-45
FlashPt = 93 °C
Autoignition =

Benzal chloride is an organic compound with the formula C6H5CHCl2. [cite web
url=http://www.inchem.org/documents/icsc/icsc/eics0101.htm
title=BENZAL CHLORIDE
publisher=International Programme on Chemical Safety
accessdate=2007-10-30] 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: [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.] : C6H5CHCl2 + H2O → C6H5CHO + 2 HCl

Addition of strong base to benzal chloride generates phenylcarbene.

References


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  • benzal chloride — noun : a colorless highly refractive liquid compound C6H5CHCl2 made by chlorinating toluene and used especially in the synthesis of benzaldehyde; α,α dichloro toluene called also benzylidene chloride * * * Chem. a colorless, oily liquid, C7H6Cl2 …   Useful english dictionary

  • benzal chloride — Chem. a colorless, oily liquid, C7H6Cl2, used chiefly in the synthesis of benzaldehyde, and in the manufacture of dyes. Also called benzyl dichloride, benzylidene chloride. [1875 80] * * * …   Universalium

  • benzylidene chloride — noun : benzal chloride * * * Chem. See benzal chloride …   Useful english dictionary

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  • benzaldehyde — /ben zal deuh huyd /, n. Chem. a colorless or yellowish, water soluble, volatile oil, C7H6O, having a bitter, almondlike odor, used chiefly in the organic synthesis of dyes, perfumes, and flavors, and as a solvent; artificial oil of bitter almond …   Universalium

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