Mercury(II) Cyanide


[592-04-1]  · C2HgN2  · Mercury(II) Cyanide  · (MW 252.63)

(glycosidation reagent1)

Alternate Name: mercuric cyanide.

Physical Data: mp 320 °C dec; d 3.996 g cm-3.

Solubility: insol benzene; sol H2O, alcohol, NH3; slightly sol ether.

Form Supplied in: colorless, odorless, tetragonal crystals or white powder.

Handling, Storage, and Precautions: acute poison. Exposure to all mercury compounds is to be strictly avoided. Releases toxic Hg fumes when heated to decomposition. Protect from light.

Mercury(II) cyanide is sometimes superior to Ag2CO3 in the formation of glycosides from bromo sugars with isolated yields up to 90%; MeNO2 or CH2Cl2 seem to be the best solvents.1 Evomonoside, a steroidal cardioactive glycoside, has been prepared from digitoxigenin in 44% yield;2 attempted synthesis with Ag2CO3 failed because of an extensive elimination of the 14b-OH of the aglycon.2 Nucleosides can be obtained from pyrimidine bases and protected halo sugars by heating with Hg(CN)2 in an inert solvent (toluene, MeCN, or MeNO2).3

1. (a) Helferich, B.; Weis, K. CB 1956, 89, 314. (b) Helferich, B.; Steinpreis, R. CB 1958, 91, 1794.
2. Zorbach, W. W.; Valiaveedan, G. D.; Kashelikar, D. V. JOC 1962, 27, 1766.
3. (a) Rogers, G. T.; Ulbricht, T. L. V. CC 1969, 508. (b) Rogers, G. T.; Ulbricht, T. L. V. JCS(C) 1969, 2450.

Pavel Ko&cbreve;ovský

University of Leicester, UK

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