diphenylmercury

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|verifiedrevid = 443697603

|ImageFile = Diphenylmercury-2D-skeletal.png

|ImageFile1 = Diphenylmercury-from-xtal-3D-balls.png

|Section1={{Chembox Identifiers

|CASNo_Ref = {{cascite|correct|??}}

|CASNo = 587-85-9

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 9JF9FUI57J

|EINECS = 209-606-1

|PubChem = 11488

|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

|ChemSpiderID = 11004

|SMILES = c1ccc(cc1)[Hg]c2ccccc2

|InChI = 1/2C6H5.Hg/c2*1-2-4-6-5-3-1;/h2*1-5H;/rC12H10Hg/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H

|InChIKey = HWMTUNCVVYPZHZ-CYESTLPZAK

|StdInChI_Ref = {{stdinchicite|changed|chemspider}}

|StdInChI = 1S/2C6H5.Hg/c2*1-2-4-6-5-3-1;/h2*1-5H;

|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|StdInChIKey = HWMTUNCVVYPZHZ-UHFFFAOYSA-N }}

|Section2={{Chembox Properties

|Formula = {{chem2|Hg(C6H5)2}}

|C=12|H=10|Hg=1

|Appearance = white solid

|Density = 2.318 g/cm3{{cite book | title = CRC Handbook of Chemistry and Physics, 89th Edition | last = Lide | first = D. R. | year = 2008 | publisher = CRC Press | isbn = 978-0-8493-0488-0 | pages = 3–518}}

|MeltingPtC = 121 to 123

|BoilingPtC = 204

|BoilingPt_ref =

|Solubility = slightly soluble in ethanol, diethyl ether; soluble in benzene, chloroform}}

|Section7={{Chembox Hazards

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|Section9 = {{Chembox Related

|OtherCompounds = {{ubl|Diphenylzinc|Phenylcopper|Phenylsodium}}

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Diphenylmercury is the organomercury compound with the formula {{chem2|Hg(C6H5)2}}. It is a white solid.{{cite journal |author1=Glidewell, C. |author2=Low, J. N. |author3=Wardell, J. L. | title = Diphenylmercury, redetermined at 120 K: sheets built from a single C-H···π(arene) hydrogen bond | journal = Acta Crystallographica C | year = 2005 | volume = 61 | issue = 2 | pages = m107–m108 | doi = 10.1107/S0108270104034134 | pmid = 15695887 | url = http://journals.iucr.org/c/issues/2005/02/00/sk1803/sk1803.pdf | doi-access = free}} The compound is of historic interest as a particularly stable organometallic compound but it finds few uses because of its high toxicity.

Preparation

Commercially available, this compound can be prepared by several routes. It results from treating phenylmercury acetate with sodium stannite,{{cite journal | last1 = Maynard | first1 = J. L. | title = The Direct Mercuration of Benzene and the Preparation of Mercury Diphenyl | journal = Journal of the American Chemical Society | year = 1924 | volume = 46 | issue = 6 | pages = 1510–1512 | doi = 10.1021/ja01671a024}} by the reaction of mercuric halides with phenylmagnesium bromide,{{cite journal | last1 = Borgstrom | first1 = P. | last2 = Dewar | first2 = M. M. | title = The Preparation of Mercury Diphenyl by Use of the Grignard Reagent | journal = Journal of the American Chemical Society | year = 1929 | volume = 51 | issue = 11 | pages = 3387–3389 | doi = 10.1021/ja01386a030}} and the reaction of bromobenzene with sodium amalgam.{{OrgSynth | author = Calvery, H. O. | title = Diphenylmercury | year = 1929 | volume = 9 | pages = 54 | collvol = 1 | collvolpages = 228 | prep = cv1p0228}}

Safety

Diphenylmercury is highly toxic.

References