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.
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| Names | |
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| Preferred IUPAC name
1,1′-(Dichloromethylene)dibenzene | |
| Other names
Dichlorodiphenylmethane
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| Identifiers | |
3D model (JSmol)
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| 1910601 | |
| ChemSpider | |
| ECHA InfoCard | 100.016.486 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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)[2] |
| Boiling point | 193 °C (379 °F; 466 K) at 32 torr[1] |
| 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
editIt 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
editIt 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
edit- ^ 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.
- ^ 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.
- ^ a b Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses; Collected Volumes, vol. 1, p. 95.
- ^ 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.
- ^ 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.
- ^ "Preps in which diphenyldichloromethane appears". www.orgsyn.org. Archived from the original on 25 August 2005. Retrieved 27 March 2013.
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