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Benzyl chloride (100-44-7)

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 Chemistry

Molecular formula :C7H7Cl
Molar mass :126.58 g/mol
Molecular Structure:
Density: 1.100 g/cm3
Melting point: -39 °C
Boiling point: 179 °C
Flash point: 165 °F
density: 1.1 g/mL at 25 °C(lit.)
vapor density: 4.36 (vs air)
vapor pressure: 10.3 mm Hg ( 60 °C)
refractive index: n20/D 1.538(lit.)
storage temp.: 0-6°C
Water Solubility: 0.3 g/L (20 oC)

 Uses
Industrially, benzyl chloride(100-44-7)  is the precursor to benzyl ESTERS , and benzyl ESTERS are used as used as  plasticizer, and perfumes. Phenylacetic acid, a precursor to pharmaceuticals, arises via benzyl cyanide, which is generated by treatment of benzyl chloride(100-44-7)  with sodium cyanide. Quaternary ammonium salts, used as surfactants, are readily formed by alkylation of tertiary amines with benzyl chloride(100-44-7).
Benzyl chloride(100-44-7)  also reacts readily with metallic MAGNESIUM to produce a Grignard Reagent. It is preferable over benzyl bromide for the preparation of benzylic Grignard reagent, since the reaction of the bromide with MAGNESIUM tends to form the Wurtz-coupling product, 1,2-diphenylethane.
In organic synthesis, benzyl chloride(100-44-7)  is used for the introduction of the benzyl protecting group for alcohols, yielding the corresponding benzyl ether, and carboxylic acids, yielding the corresponding benzyl ester. It may be used in the synthesis of amphetamine-class drugs, and for this reason sales of benzyl chloride(100-44-7) are monitored as a List II drug precursor chemical by the US Drug Enforcement Administration.
 Production
Benzyl chloride(100-44-7) is prepared industrially by the gas-phase photochemical reaction of TOLUENE with chlorine:
C6H5CH3 + Cl2 →C6H5CH2Cl + HCl
In this way,  Benzyl chloride approximates 100,000 tonnes are produced annually. The reaction proceeds via free radical, involving the intermediacy of the chlorine atoms.Side products of the reaction include  benzotrichloride and enzal chloride.
Other methods exist, such as the Blanc chloromethylation of benzene. Benzyl chloride was first prepared from treatment of Benzyl Alcohol with hydrochloric acid.
 Safety Profile

Hazard Codes:  T
The Risk Statements information of Benzyl chloride(100-44-7):
22:  Harmful if swallowed 
23:  Toxic by inhalation 
41:  Risk of serious damage to eyes 
45:  May cause cancer 
37/38:  Irritating to respiratory system and skin 
48/22:  Harmful: danger of serious damage to health by prolonged exposure if swallowed 
The Safety Statements information of Benzyl chloride(100-44-7):
53:  Avoid exposure - obtain special instruction before use 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
RIDADR: UN 1738 6.1/PG 2
WGK Germany: 3

  • Benzyl chloride Basic information

  • Product Name:Benzyl chloride
  • CAS No:100-44-7
  • Formula:C7H7Cl
  • Molecular Structure of (<span class=bigs><a href=/cas-100/100-44-7.html />100-44-7</a></span>) (Benzyl Chloride)