Lithium cyanide

Lithium cyanide[1][2][3]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.554 Edit this at Wikidata
EC Number
  • 219-308-3
UN number 1935
  • InChI=1S/CN.Li/c1-2;/q-1;+1
    Key: JORQDGTZGKHEEO-UHFFFAOYSA-N
  • [Li+].[C-]#N
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
GHS labelling:[4]
GHS02: FlammableGHS06: ToxicGHS09: Environmental hazard
Danger
H226, H300, H310, H330, H410
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P310, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
0
1
Flash point 57 °C (135 °F; 330 K)
N/A
Safety data sheet (SDS) 742899
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).

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, vol. 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, archived from the original on 2017-07-24, retrieved 2012-12-09
  3. ^ Material Safety Data Sheet: Lithium Cyanide, 0.5M Solution in N,N-Dimethylformamide, Fisher Scientific, 16 June 1999
  4. ^ "Lithium cyanide". pubchem.ncbi.nlm.nih.gov. Retrieved 19 December 2021.
  5. ^ Livinghouse, Tom (1981). "Trimethylsilyl Cyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10.15227/orgsyn.060.0126.
  6. ^ 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.
  7. ^ Harusawa, Shinya; Yoneda, Ryuji; Omori, Yukie; Kurihara, Takushi (1987). "Non-aqueous cyanation of halides using lithium cyanide". Tetrahedron Letters. 28 (36). Elsevier: 4189–4190. doi:10.1016/S0040-4039(00)95575-8.