Diphenyldichloromethane

Chemical compound From Wikipedia, the free encyclopedia

Diphenyldichloromethane is an organic compound with the formula (C6H5)2CCl2. It is a colorless solid that is used as a precursor to other organic compounds.

Quick facts Names, Identifiers ...
Diphenyldichloromethane
Names
Preferred IUPAC name
1,1′-(Dichloromethylene)dibenzene
Other names
Dichlorodiphenylmethane
Identifiers
3D model (JSmol)
1910601
ChemSpider
ECHA InfoCard 100.016.486 Edit this at Wikidata
UNII
  • InChI=1S/C13H10Cl2/c14-13(15,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H checkY
    Key: OPTDDWCXQQYKGU-UHFFFAOYSA-N checkY
  • c1ccc(cc1)C(c2ccccc2)(Cl)Cl
Properties
C13H10Cl2
Molar mass 237.12 g·mol−1
Appearance slightly yellow liquid
Density 1.235 g/cm3
Melting point 146 to 150 °C (295 to 302 °F; 419 to 423 K)[1]
Boiling point 193 °C (379 °F; 466 K) at 32 torr[2]
Hazards
Flash point 110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

It is prepared from carbon tetrachloride and anhydrous aluminium chloride as catalyst in a double Friedel-Crafts alkylation of benzene.[3] Alternatively, benzophenone is treated with phosphorus pentachloride:[4]

(C6H5)2CO + PCl5 → (C6H5)2CCl2 + POCl3

Reactions

It undergoes hydrolysis to benzophenone.[3]

(C6H5)2CCl2 + H2O → (C6H5)2CO + 2 HCl

Reductive dehalogenation of diphenyldichloromethane with copper or with nickel gives tetraphenylethylene:[5][6]

(C6H5)2CCl2 + 4 Cu → (C6H5)2C=C(C6H5)2 + 4 CuCl

References

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