Diphenyldichloromethane

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.

Diphenyldichloromethane

Names
Preferred IUPAC name 1,1′-(Dichloromethylene)dibenzene
Other names Dichlorodiphenylmethane
Identifiers
CAS Number	2051-90-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1910601
ChemSpider	15492 Y
ECHA InfoCard	100.016.486
PubChem CID	16327
UNII	81FEZ29AK6 Y
CompTox Dashboard (EPA)	DTXSID9062148
InChI InChI=1S/C13H10Cl2/c14-13(15,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Y Key: OPTDDWCXQQYKGU-UHFFFAOYSA-N Y
SMILES c1ccc(cc1)C(c2ccccc2)(Cl)Cl
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

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