:Diphenyldichloromethane

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| Watchedfields = changed

| verifiedrevid = 431344616

| ImageFile = Diphenyldichloromethane.svg

| ImageSize =

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| 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

| MeltingPt_ref = {{cite journal|last=Ballester|first=Manuel|author2=Juan Riera-Figueras |author3=Juan Castaner |author4=Carlos Badfa |author5=Jose M. Monso |year=1971|title=Inert carbon free radicals. I. Perchlorodiphenylmethyl and perchlorotriphenylmethyl radical series|journal=Journal of the American Chemical Society|volume=93|issue=9|pages=2215–2225|issn=0002-7863|doi=10.1021/ja00738a021}}

| BoilingPtC = 193

| BoilingPt_notes = at 32 torr{{cite journal|last=Andrews|first=L. J.|author2=W. W. Kaeding|year=1951|journal=Journal of the American Chemical Society|volume=73 |issue=3|pages=1007–1011|issn=0002-7863 |doi=10.1021/ja01147a036 | title = The Formation of Benzophenone and its Diethylketal in the Ethanolysis of Diphenyldichloromethane}}

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 110

| AutoignitionPtC =

}}

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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 }}

References

{{Reflist}}

Category:Phenyl compounds

Category:Organochlorides

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