:Diphenyldichloromethane
{{Chembox
| Watchedfields = changed
| verifiedrevid = 431344616
| ImageFile = Diphenyldichloromethane.svg
| ImageSize =
| ImageAlt =
| PIN = 1,1′-(Dichloromethylene)dibenzene
| OtherNames = Dichlorodiphenylmethane
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2051-90-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 81FEZ29AK6
| Beilstein = 1910601
| PubChem = 16327
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 15492
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI =1S/C13H10Cl2/c14-13(15,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OPTDDWCXQQYKGU-UHFFFAOYSA-N
| SMILES = c1ccc(cc1)C(c2ccccc2)(Cl)Cl}}
|Section2={{Chembox Properties
| C=13 | H=10 | Cl=2
| Appearance = slightly yellow liquid
| Density = 1.235 g/cm3
| MeltingPtC = 146 to 150
| BoilingPtC = 193
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 110
| AutoignitionPtC =
}}
}}
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.{{OrgSynth | author = Marvel, C. S. | author2 = Sperry, W. M. | title = Benzophenone | prep = cv1p0095 | collvol = 1 | collvolpages = 95 | year = 1941}} Alternatively,
benzophenone is treated with phosphorus pentachloride:{{cite journal|last=Spaggiari|first=Alberto|author2=Daniele Vaccari |author3=Paolo Davoli |author4=Giovanni Torre |author5=Fabio Prati |year=2007|title=A Mild Synthesis of Vinyl Halides andgem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents|journal=The Journal of Organic Chemistry|volume=72|issue=6|pages=2216–2219|issn=0022-3263|pmid=17295542|doi=10.1021/jo061346g}}
:(C6H5)2CO + PCl5 → (C6H5)2CCl2 + POCl3
Reactions
It undergoes hydrolysis to benzophenone.
:(C6H5)2CCl2 + H2O → (C6H5)2CO + 2 HCl
It is used in the synthesis of tetraphenylethylene,{{cite journal|last=Inaba|first=S|year=1982|title=Metallic nickel as a reagent for the coupling of aromatic and benzylic halides|journal=Tetrahedron Letters|volume=23|issue=41|pages=4215–4216|issn=0040-4039|doi=10.1016/S0040-4039(00)88707-9}}
diphenylmethane imine hydrochloride and benzoic anhydride.{{cite web |title=Preps in which diphenyldichloromethane appears |url=http://www.orgsyn.org/orgsyn/chemname.asp?nameID=33200 |publisher=www.orgsyn.org |access-date=27 March 2013 |url-status=dead |archive-url=https://web.archive.org/web/20050825082846/http://www.orgsyn.org/orgsyn/chemname.asp?nameID=33200 |archive-date=25 August 2005 }}