Diphenyldichloromethane

Diphenyldichloromethane
Names
	IUPAC name diphenyldichloromethane
	Other names bis-chlorodiphenylmethane; bisphenyldichloromethane; diphenyl-dichloromethane; dichlorodiphenylmethane; α,α-dichlorodiphenylmethane; 1,1-dichloro-1,1-diphenylmethane; 1,1-dichlorodiphenylmethane; benzophenone dichloride;
Identifiers
CAS Number	2051-90-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1910601
ChemSpider	15492 ;
ECHA InfoCard	100.016.486
PubChem CID	16327;
	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)[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).
	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

↑ 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.
↑ 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.
1 2 Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses. ; Collective Volume, 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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[Ballester1971-1] 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.

[Andrews1951-2] 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.

[Marvel-3] 1 2 Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses. ; Collective Volume, 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.