Lithium cyanide
Toxic crystalline salt
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Identifiers | |||
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CAS Number |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.017.554 | ||
EC Number |
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PubChem CID |
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UN number | 1935 | ||
CompTox Dashboard (EPA) |
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InChI
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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 (kH) | N/A | ||
Structure | |||
Crystal structure | - | ||
Coordination geometry | Fourfold | ||
Hazards | |||
GHS labelling:[4] | |||
Pictograms | |||
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) | 4 0 1 | ||
Flash point | 57 °C (135 °F; 330 K) | ||
Autoignition temperature | 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). 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.
- v
- t
- e
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- Li1+xAlxGe2−x(PO4)3
- LiAlH4
- LiAlO2
- LiAl1+xTi2−x(PO4)3
- LiAs
- LiAsF6
- Li3AsO4
- LiAt
- Li[AuCl4]
- LiB(C2O4)2
- LiB(C6F5)4
- LiBF4
- LiBH4
- LiBO2
- LiB3O5
- Li2B4O7
- 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
- Li0.9Mo6O17
- 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
- LiZr2(PO4)3
- Li2ZrO3
- Hemolithin (extraterrestrial protein)
- Organolithium reagents
- CH3COOLi
- C4H6LiNO4
- LiC2F6NO4S2
- LiN(SiMe3)2
- Li3C6H5O7
- C5H5Li
- LiN(C3H7)2
- (C6H5)2PLi
- C18H35LiO3
- C6H13Li
- C4H9Li
- CH3CHLiCH2CH3
- (CH3)3CLi
- C12H28BLi
- CH3Li
- Li+C10H8−
- C5H11Li
- C5H3LiN2O4
- C6H5Li
- LiC2CH3
- LiO2C(CH2)16CH3
- C4H5LiO4
- LiEt3BH
- LiOC(CH3)3
- C9H18LiN
- LiC2H3 Vinyllithium
- LiC
11H
23COO
- 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 LiAlSi4010
- Pezzottaite Cs(Be2Li)Al2Si6O18
- Rossmanite
- Saliotite
- Sogdianite
- Spodumene LiAl(SiO3)2
- Sugilite
- Tiptopite
- Tourmaline
- Triphylite LiFePO4
- Zabuyelite Li2CO3
- Zektzerite
- Zinnwaldite
- LixBey
- HLiHe+
- LiFHeO
- LiHe2
- (HeO)(LiF)2
- La2/3-xLi3xTiO3He
- Aluminium–lithium alloys
- Heteroatom-promoted lateral lithiation
- LB buffer
- Lithium atom
- Lithium medication
- LiNixCoyAlzO2
- LiNixMnyCozO2
- Lithium soap
- Lithium Triangle
- Lucifer yellow
- Magnesium–lithium alloys
- NASICON
- Environmentally friendly red light flare