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
3D model (JSmol)
1910601
ChemSpider
ECHA InfoCard 100.016.486
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 colorless solid
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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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

It is used in the synthesis of tetraphenylethylene,[5] diphenylmethane imine hydrochloride and benzoic anhydride.[6]

References
  1. Ballester, Manuel; Juan Riera-Figueras; Juan Castaner; Carlos Badfa; Jose M. Monso (1971). "Inert carbon free radicals. I. Perchlorodiphenylmethyl and perchlorotriphenylmethyl radical series". Journal of the American Chemical Society. 93 (9): 2215–2225. doi:10.1021/ja00738a021. ISSN 0002-7863.
  2. Andrews, L. J.; W. W. Kaeding (1951). "The Formation of Benzophenone and its Diethylketal in the Ethanolysis of Diphenyldichloromethane". Journal of the American Chemical Society. 73 (3): 1007–1011. doi:10.1021/ja01147a036. ISSN 0002-7863.
  3. Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses.; Collective Volume, vol. 1, p. 95
  4. 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. doi:10.1021/jo061346g. ISSN 0022-3263. PMID 17295542.
  5. Inaba, S (1982). "Metallic nickel as a reagent for the coupling of aromatic and benzylic halides". Tetrahedron Letters. 23 (41): 4215–4216. doi:10.1016/S0040-4039(00)88707-9. ISSN 0040-4039.
  6. "Preps in which diphenyldichloromethane appears". www.orgsyn.org. Archived from the original on 25 August 2005. Retrieved 27 March 2013.


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