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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

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.

v t e Lithium compounds (list)
Inorganic (list)	Li₂ LiAlCl₄ Li_1+xAl_xGe_2−x(PO₄)₃ LiAlH₄ LiAlO₂ LiAl_1+xTi_2−x(PO₄)₃ LiAs LiAsF₆ Li₃AsO₄ LiAt Li[AuCl₄] LiB(C₂O₄)₂ LiB(C₆F₅)₄ LiWF₆ LiBF₄ LiBH₄ LiBO₂ LiB₃O₅ Li₂B₄O₇ LiAsF₆ Li₂SnF₆ Li₂TiF₆ Li₂ZrF₆ Li₂B₄O₇·5H₂O LiBSi₂ LiBr LiBr·2H₂O LiBrO LiBrO₂ LiBrO₃ LiBrO₄ Li₂C₂ LiCF₃SO₃ CH₃CH(OH)COOLi LiC₂H₂ClO₂ LiC₂H₃IO₂ Li(CH₃)₂N LiCHO₂ LiCH₃O LiC₂H₅O LiCN Li₂CN₂ LiCNO Li₂CO₃ Li₂C₂O₄ LiCl LiCl·H₂O LiClO LiFO LiClO₂ LiClO₃ LiClO₄ LiCoO₂ Li₂CrO₄ Li₂CrO₄·2H₂O Li₂Cr₂O₇ CsLiB₆O₁₀ LiD LiF Li₂F LiF₄Al Li₃F₆Al FLiBe LiFePO₄ FLiNaK LiGaH₄ Li₂GeF₆ Li₂GeO₃ LiGe₂(PO₄)₃ LiH LiH₂AsO₄ Li₂HAsO₄ LiHCO₃ Li₃H(CO₃)₂ LiH₂PO₃ LiH₂PO₄ LiHSO₃ LiHSO₄ LiHe LiI LiIO LiIO₂ LiIO₃ LiIO₄ Li₂IrO₃ Li₇La₃Zr₂O₁₂ LiMn₂O₄ Li₂MoO₄ Li_0.9Mo₆O₁₇ LiN₃ Li₃N LiNH₂ Li₂NH LiNO₂ LiNO₃ LiNO₃·H₂O Li₂N₂O₂ LiNa Li₂NaPO₃ LiNaNO₂ LiNbO₃ Li₂NbO₃ LiO⁻ LiO₂ LiO₃ Li₂O Li₂O₂ LiOH Li₃P LiPF₆ Li₃PO₄ Li₂HPO₃ Li₂HPO₄ Li₃PO₃ Li₃PO₄ Li₂Po Li₂PtO₃ Li₂RuO₃ Li₂S LiSCN LiSH LiSO₃F Li₂SO₃ Li₂SO₄ Li[SbF₆] Li₂Se Li₂SeO₃ Li₂SeO₄ LiSi Li₂SiF₆ Li₄SiO₄ Li₂SiO₃ Li₂Si₂O₅ LiTaO₃ Li₂Te LiTe₃ Li₂TeO₃ Li₂TeO₄ Li₂TiO₃ Li₄Ti₅O₁₂ LiTi₂(PO₄)₃ LiVO₃·2H₂O Li₃V₂(PO₄)₃ Li₂WO₄ LiYF₄ Neodymium-doped LiZr₂(PO₄)₃ Li₂ZrO₃
Organic (soaps)	Hemolithin (extraterrestrial protein) Organolithium reagents Gilman reagent CH₃COOLi C₄H₆LiNO₄ LiC₂F₆NO₄S₂ LiN(SiMe₃)₂ Li₃C₆H₅O₇ C₅H₅Li LiN(C₃H₇)₂ (C₆H₅)₂PLi C₁₈H₃₅LiO₃ C₆H₁₃Li C₄H₉Li CH₃CHLiCH₂CH₃ (CH₃)₃CLi C₁₂H₂₈BLi CH₃Li Li⁺C₁₀H−8 C₅H₁₁Li C₅H₃LiN₂O₄ C₆H₅Li LiC₂CH₃ LiO₂C(CH₂)₁₆CH₃ C₄H₅LiO₄ LiEt₃BH LiOC(CH₃)₃ C₉H₁₈LiN LiC₂H₃ Vinyllithium LiC ₁₁H ₂₃COO
Minerals	Amblygonite Berezanskite Brannockite Cryolithionite Darapiosite Darrellhenryite Elbaite Fluorine Elbaite Fluor-liddicoatite Emeleusite Eucryptite LiAlSiO₄ Faizievite Hectorite Hsianghualite Jadarite LiNaSiB₃O₇OH Keatite Li(AlSi₂O₆) Kunzite Lavinskyite Lepidolite Lithiophilite LiMnPO₄ Lithiophosphate Li₃PO₄ Manandonite Manganoneptunite Nambulite Neptunite Olympite Petalite LiAlSi₄O₁₀ Pezzottaite Cs(Be₂Li)Al₂Si₆O₁₈ Rossmanite Saliotite Sogdianite Spodumene LiAl(SiO₃)₂ Sugilite Tiptopite Tourmaline Triphylite LiFePO₄ Zabuyelite Li₂CO₃ Zektzerite Zinnwaldite
Hypothetical	Li_xBe_y HLiHe⁺ LiFHeO LiHe₂ (HeO)(LiF)₂ La_2⁄3–xLi_3xTiO₃He
Other Li-related	Aluminium–lithium alloys Heteroatom-promoted lateral lithiation LB buffer Lithium atom Lithium medication LiNi_xCo_yAl_zO₂ LiNi_xMn_yCo_zO₂ Lithium soap Lithium Triangle Lucifer yellow Magnesium–lithium alloys NASICON Environmentally friendly red light flare

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