Chemistry:Lithium cyanide

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Short description: Toxic crystalline salt
Lithium cyanide[1][2][3]
Lithium-cyanide-unit-cell-3D-SF.png
Lithium-3D.png
Cyanide-ion-3D-vdW.svg
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 219-308-3
UN number 1935
Properties
LiCN
Molar mass 32.959 g/mol
Appearance White Powder
Density 1.073 g/cm3 (18 °C)
Melting point 160 °C (320 °F; 433 K) Dark coloured
Boiling point decomposes
Soluble
N/A
Structure
-
Fourfold
Hazards
Safety data sheet 742899
GHS pictograms GHS02: FlammableGHS06: ToxicGHS09: Environmental hazard
GHS Signal word Danger
H226, H300, H310, H330, H410
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P303+361+353, P304+340, P310, P320, P321, P322, P330, P361, P363
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
4
1
Flash point 57 °C (135 °F; 330 K)
N/A
Related compounds
Related compounds
Sodium cyanide, Potassium cyanide, Hydrogen cyanide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Lithium cyanide is an inorganic compound with the chemical formula LiCN. It is a toxic, white coloured, hygroscopic, water-soluble salt that finds only niche uses.

Preparation

LiCN is produced from the reaction of lithium hydroxide and hydrogen cyanide. A laboratory-scale preparation uses acetone cyanohydrin as a surrogate for HCN:[5]

(CH3)2C(OH)CN + LiH → (CH3)2CO + LiCN + H2

Uses

The compound decomposes to cyanamide and carbon when heated to a temperature close to but below 600 °C. Acids react to give hydrogen cyanide.[6]

Lithium cyanide can be used as a reagent for organic compound cyanation.[7]

RX + LiCN → RCN + LiX

References

  1. J. A. Lely, J. M. Bijvoet (1942), "The Crystal Structure of Lithium Cyanide", Recueil des Travaux Chimiques des Pays-Bas, 61, London: WILEY-VCH Verlag, doi:10.1002/recl.19420610402 
  2. Haynes, W.M (2013), "Bernard Lewis", in Bruno, Thomas., Handbook of Chemistry and Physics (93 ed.), Boca Raton, Florida: Fitzroy Dearborn, http://www.hbcpnetbase.com/, retrieved 2012-12-09 
  3. Material Safety Data Sheet: Lithium Cyanide, 0.5M Solution in N,N-Dimethylformamide, Fisher Scientific, 16 June 1999, http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=742899&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2FALDRICH%2F742899%3Flang%3Den 
  4. "Lithium cyanide" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/75478#section=Safety-and-Hazards. 
  5. Livinghouse, Tom (1981). "Trimethylsilyl Cyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10.15227/orgsyn.060.0126. 
  6. L. Pesce (2010). "Kirk-Othmer Encyclopedia of Chemical Technology". Kirk‐Othmer Encyclopedia of Chemical Technology. Wiley-VCH. doi:10.1002/0471238961.0325011416051903.a01.pub2. ISBN 978-0471238966. 
  7. Harusawa, Shinya; Yoneda, Ryuji; Omori, Yukie; Kurihara, Takushi (1987). "Non-aqueous cyanation of halides using lithium cyanide". Tetrahedron Letters (Elsevier) 28 (36): 4189–4190. doi:10.1016/S0040-4039(00)95575-8.