Diphenylmercury

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Diphenylmercury
Diphenylmercury-2D-skeletal.png
Diphenylmercury-from-xtal-3D-balls.png
Identifiers
CAS number 587-85-9 YesY
UNII 9JF9FUI57J YesY
Properties
Molecular formula C12H10Hg
Molar mass 354.80 g mol−1
Appearance white solid
Density 2.318 g cm−3[1]
Melting point 121–123 °C
Boiling point 204 °C[1]
Solubility in water slightly soluble in ethanol, diethyl ether; soluble in benzene, chloroform[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Diphenylmercury is the organomercury compound with the formula Hg(C6H5)2. It is a white solid.[2]The compound is of historic interest as a particularly stable organometallic compound but it finds few uses because of its high toxicity.

Preparation[edit]

Commercially available, this compound can been be prepared by several route. It results treating phenylmercury acetate with sodium stannite,[3] by the reaction of mercuric halides with phenylmagnesium bromide,[4] and the reaction of bromobenzene with sodium amalgam.[5]

Safety[edit]

Diphenylmercury is highly toxic.

References[edit]

  1. ^ a b c Lide, D. R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. p. 3–518. ISBN 978-0-8493-0488-0. 
  2. ^ Glidewell, C.; Low, J. N.; Wardell, J. L. (2005). "Diphenylmercury, redetermined at 120 K: sheets built from a single C-H···π(arene) hydrogen bond" (pdf). Acta Crystallographica C 61 (2): m107–m108. doi:10.1107/S0108270104034134. PMID 15695887. 
  3. ^ Maynard, J. L. (1924). "The Direct Mercuration of Benzene and the Preparation of Mercury Diphenyl". Journal of the American Chemical Society 46 (6): 1510–1512. doi:10.1021/ja01671a024. 
  4. ^ Borgstrom, P.; Dewar, M. M. (1929). "The Preparation of Mercury Diphenyl by Use of the Grignard Reagent". Journal of the American Chemical Society 51 (11): 3387–3389. doi:10.1021/ja01386a030. 
  5. ^ Calvery, H. O. (1929), "Diphenylmercury", Org. Synth. 9: 54 ; Coll. Vol. 1: 228