Lithium cyanide

Toxic crystalline salt

Lithium cyanide^[1]^[2]^[3]

Identifiers

CAS Number

2408-36-8

3D model (JSmol)

Interactive image

ChemSpider

68007

ECHA InfoCard

100.017.554

EC Number

219-308-3

PubChem CID

75478

UN number

1935

CompTox Dashboard (EPA)

DTXSID10946920

InChI

InChI=1S/CN.Li/c1-2;/q-1;+1
Key: JORQDGTZGKHEEO-UHFFFAOYSA-N

SMILES

[Li+].[C-]#N

Properties

Chemical formula

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

Solubility in water

Soluble

Henry's law
constant (k_H)

N/A

Structure

Crystal structure

Coordination geometry

Fourfold

Hazards

GHS labelling:^[4]

Pictograms

Signal word

Danger

Hazard statements

H226, H300, H310, H330, H410

Precautionary statements

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)

Flash point

57 °C (135 °F; 330 K)

Autoignition
temperature

N/A

Safety data sheet (SDS)

742899

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

Chemical compound

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

^ 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
^ 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
^ Material Safety Data Sheet: Lithium Cyanide, 0.5M Solution in N,N-Dimethylformamide, Fisher Scientific, 16 June 1999
^ "Lithium cyanide". pubchem.ncbi.nlm.nih.gov. Retrieved 19 December 2021.
^ Livinghouse, Tom (1981). "Trimethylsilyl Cyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10.15227/orgsyn.060.0126.
^ 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.
^ 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.