Diphenylmercury

Diphenylmercury
Identifiers
CAS Number	587-85-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	11004 ;
ECHA InfoCard	100.008.734
EC Number	209-606-1;
PubChem CID	11488;
UNII	9JF9FUI57J ;
CompTox Dashboard (EPA)	DTXSID3042130 ;
	InChI InChI=1S/2C6H5.Hg/c21-2-4-6-5-3-1;/h21-5H; Key: HWMTUNCVVYPZHZ-UHFFFAOYSA-N ; InChI=1/2C6H5.Hg/c21-2-4-6-5-3-1;/h21-5H;/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

Lide, D. R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–518. ISBN 978-0-8493-0488-0.
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.
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.
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.
Calvery, H. O. (1929). "Diphenylmercury". Organic Syntheses. 9: 54.; Collective Volume, 1, p. 228

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[CRC-1] Lide, D. R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–518. ISBN 978-0-8493-0488-0.

[Glidewell-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, 1, p. 228