Diphenyldichloromethane

Diphenyldichloromethane

Names
Preferred IUPAC name 1,1′-(Dichloromethylene)dibenzene
Other names Dichlorodiphenylmethane
Identifiers
CAS Number	2051-90-3  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1910601
ChemSpider	15492  Y
ECHA InfoCard	100.016.486
PubChem CID	16327
UNII	81FEZ29AK6  Y
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 Y Key: OPTDDWCXQQYKGU-UHFFFAOYSA-N Y
SMILES c1ccc(cc1)C(c2ccccc2)(Cl)Cl
Properties
Chemical formula	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) [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). Y  verify  (what is  YN ?) 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

Reductive dehalogenation of diphenyldichloromethane with copper or with nickel gives tetraphenylethylene: ^{[5] [6]}

(C₆H₅)₂CCl₂ + 4 Cu → (C₆H₅)₂C=C(C₆H₅)₂ + 4 CuCl

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 ; Collected Volumes, 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. hdl: 11380/310743 . ISSN   0022-3263. PMID   17295542.
5. Robert E. Buckles George M. Matlack (1951). "Tetraphenylethylene". Organic Syntheses . 31: 104. doi:10.15227/orgsyn.031.0104.
6. 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.