Diphenyldichloromethane

Diphenyldichloromethane
Names
	Preferred IUPAC name 1,1'-(Dichloromethylene)dibenzene
	Other names Dichlorodiphenylmethane
Identifiers
CAS Number	2051-90-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1910601
ChemSpider	15492 ;
ECHA InfoCard	100.016.486
PubChem CID	16327;
UNII	81FEZ29AK6 ;
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 Key: OPTDDWCXQQYKGU-UHFFFAOYSA-N ;
	SMILES c1ccc(cc1)C(c2ccccc2)(Cl)Cl;
Properties
Chemical formula	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)
Boiling point	193 °C (379 °F; 466 K) at 32 torr
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). verify (what is ?) Infobox references

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.^[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

^ 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{{cite journal}}: CS1 maint: multiple names: authors list (link); 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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[Andrews1951-1] 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.

[Ballester1971-2] 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.

[Marvel-3] Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 95.

[Spaggiari2007-4] 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.

[Inaba1982-5] 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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