Diphenylmercury

Diphenylmercury
Identifiers
CAS number	587-85-9 Y
UNII	9JF9FUI57J Y
Properties
Molecular formula	C12H10Hg
Molar mass	354.80 g mol−1
Density	2.318 g cm−3[1]
Boiling point	204 °C[1]
Solubility in water	slightly soluble in ethanol, diethyl ether; soluble in benzene, chloroform[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diphenylmercury is a colourless, crystalline^[2] organomercury compound with the chemical formula C₁₂H₁₀Hg. It can be synthesised by the reaction of a 2:1 molar ratio of mercury(II) chloride and methyltriphenyltin in ethanol.^[2] As with almost all organomercury compounds, the coordination geometry at mercury is linear.^[2]

Preparation

Commercially available, the synthesis of this compound has been variously described in the literature. Diphenylmercury may be prepared by the reaction of phenylmercury acetate with benzene in the presence of sodium stannite,^[3] by the reaction of mercury halides with phenylmagnesium bromide,^[4] and the reaction of bromobenzene with sodium amalgam.^[5]

References

1. ^ ^{a b c} Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. p. 3–518. ISBN 978-0849304880. 
2. ^ ^{a b c} C. Glidewell, J. N. Low, J. L. Wardell (2005). "Diphenylmercury, redetermined at 120 K: sheets built from a single C-H…π(arene) hydrogen bond". Acta Cryst. C61 (Pt 2): m107–m108. doi:10.1107/S0108270104034134. PMID 15695887. 
3. ^ Maynard, J. Lewis (1924). "The Direct Mercuration of Benzene and the Preparation of Mercury Dipheny". J. Am. Chem. Soc. 46 (6): 1510. doi:10.1021/ja01671a024. 
4. ^ Borgstrom, P.; Dewar, Margaret M. (1929). "The Preparation of Mercury Diphenyl by use of the Grignard Reagent". J. Am. Chem. Soc. 51 (11): 3387. doi:10.1021/ja01386a030. 
5. ^ H. O. Calvery, "Diphenylmercury", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0228 ; Coll. Vol. 1: 228