Diphenylmercury

Diphenylmercury
Identifiers
CAS Number
  • 587-85-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 11004 ☒N
ECHA InfoCard 100.008.734 Edit this at Wikidata
EC Number
  • 209-606-1
PubChem CID
  • 11488
UNII
  • 9JF9FUI57J checkY
CompTox Dashboard (EPA)
  • DTXSID3042130 Edit this at Wikidata
InChI
  • 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
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
Chemical compound

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. ^ a b c 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; Collected Volumes, vol. 1, p. 228.
  • v
  • t
  • e
Mercury(I)
  • HgH
  • Hg2H2
  • Hg2Br2
  • Hg2Cl2
  • Hg2F2
  • Hg2I2
  • Hg2(NO3)2
  • Hg2O
  • Hg2CO3
  • Hg2SO4
  • Hg2S (hypothetical)
Mercury(II)
  • HgH2
  • HgNH2Cl
  • HgSe
  • HgS
  • HgTe
  • Hg(O2CCH3)2
  • HgBr2
  • HgCl2
  • Hg(CN)2
  • HgF2
  • Hg(OH)2
  • HgI2
  • Hg(NO3)2
  • HgO
  • HgSO4
  • Hg(SCN)2
  • Hg(CNO)2
  • Hg3N2
  • Hg(Si(CH3)3)2
  • K2HgI4
Organomercury
compounds
  • Hg(CH3)2
  • Hg(C2H5)2
  • Hg(C6H5)2
  • HgC6H5CH3CO2
  • HgC6H5OB(OH)2
  • HgC6H5NO3
  • HgC6H5CCl3
  • HgClC6H4CO2H
  • HgOHCH2CHOCH3CH2(NHCO)
  • C
    36    H
    70    HgO
    4
  • HgOHCH2CHOCH3CH2NHCOC6H4OCH2CO2H
  • Na2HgOHC6HOBrC6H2OBrOCHC6H4CO2
  • HgOC6H2CH3NO2
  • NaHgC2H5SC6H4CO2
Mercury(IV)
  • HgF4 (hypothetical)
Amalgams
Mercury cations
  • Hg2+
  • Hg22+
  • Hg32+
  • Hg42+
  • Hg34+
  • HgCH3+
  • HgC2H5+
  • HgC6H5+