Lithium cyanide

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

Lithium cyanide[1][2][3]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.554
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 colored
Boiling point N/A
Soluble
N/A
Structure
-
Fourfold
Hazards
Safety data sheet 742899
T+, Very Toxic N, Dangerous for the environment
R-phrases (outdated) 26/27/28-32-50/53
S-phrases (outdated) 7-28-29-45-60-61
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 code
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

Preparation

LiCN arises from the interaction of lithium hydroxide and hydrogen cyanide. A laboratory-scale preparation uses acetone cyanohydrin as a surrogate for HCN: [4]

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

Reactions

The compound decomposes to cyanamide and carbon when heated to a temperature close to but below 600°C. Acids react to give hydrogen cyanide.[5]

Lithium cyanide can be used as a reagent for cyanation.[6]

RX + LiCN → RCN

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. (ed.), Handbook of Chemistry and Physics (93 ed.), Boca Raton, Florida: Fitzroy Dearborn
  3. Material Safety Data Sheet: Lithium Cyanide, 0.5M Solution in N,N-Dimethylformamide, Fisher Scientific, 16 June 1999
  4. Tom Livinghouse (1981). "Trimethylsilyl Cyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10.15227/orgsyn.060.0126.CS1 maint: uses authors parameter (link)
  5. L. Pesce (2010). "Cyanides". Kirk-Othmer Encyclopedia of Chemical Technology. Kirk‐Othmer Encyclopedia of Chemical Technology. Wiley-VCH. doi:10.1002/0471238961.0325011416051903.a01.pub2. ISBN 978-0471238966.
  6. 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.
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