Diphenylmercury

Diphenylmercury

Identifiers
CAS Number	587-85-9
ChemSpider	11004
EC Number	209-606-1
Jmol interactive 3D	Image
PubChem	11488
UNII	9JF9FUI57J
InChI InChI=1S/2C6H5.Hg/c2*1-2-4-6-5-3-1;/h2*1-5H; Key: HWMTUNCVVYPZHZ-UHFFFAOYSA-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
SMILES c1ccc(cc1)[Hg]c2ccccc2
Properties
Chemical formula	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]
Solubility in water	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

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

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. 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, p. 228