Diphenyldichloromethane Explained

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.

Synthesis

It is prepared from carbon tetrachloride and anhydrous aluminium chloride as catalyst in a double Friedel-Crafts alkylation of benzene. Alternatively,benzophenone is treated with phosphorus pentachloride:^[1]

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

Reactions

It undergoes hydrolysis to benzophenone.

(C₆H₅)₂CCl₂ + H₂O → (C₆H₅)₂CO + 2 HClIt is used in the synthesis of tetraphenylethylene,^[2] diphenylmethane imine hydrochloride and benzoic anhydride.^[3]

Notes and References

1. Spaggiari. Alberto. Daniele Vaccari . Paolo Davoli . Giovanni Torre . Fabio Prati . 2007. A Mild Synthesis of Vinyl Halides andgem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents. The Journal of Organic Chemistry. 72. 6. 2216–2219. 0022-3263. 17295542. 10.1021/jo061346g.
2. Inaba. S. 1982. Metallic nickel as a reagent for the coupling of aromatic and benzylic halides. Tetrahedron Letters. 23. 41. 4215–4216. 0040-4039. 10.1016/S0040-4039(00)88707-9.
3. Web site: Preps in which diphenyldichloromethane appears . www.orgsyn.org . 27 March 2013 . dead . https://web.archive.org/web/20050825082846/http://www.orgsyn.org/orgsyn/chemname.asp?nameID=33200 . 25 August 2005 .