Diphenylmercury

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.

Diphenylmercury
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.734
EC Number
  • 209-606-1
UNII
  • InChI=1S/2C6H5.Hg/c2*1-2-4-6-5-3-1;/h2*1-5H; ☒N
    Key: HWMTUNCVVYPZHZ-UHFFFAOYSA-N ☒N
  • 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
    Key: HWMTUNCVVYPZHZ-CYESTLPZAK
  • c1ccc(cc1)[Hg]c2ccccc2
Properties
C12H10Hg
Molar mass 354.80 g mol−1
Appearance white solid
Density 2.318 g cm−3[1]
Melting point 121 to 123 °C (250 to 253 °F; 394 to 396 K)
Boiling point 204 °C (399 °F; 477 K)[1]
slightly soluble in ethanol, diethyl ether; soluble in benzene, chloroform[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Commercially available, this compound can be prepared by several routes. It results from 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

Diphenylmercury is highly toxic.

References
  1. Lide, D. R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 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". Organic Syntheses. 9: 54.; Collective Volume, vol. 1, p. 228
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