Lithium cyanide

Last updated
Lithium cyanide [1] [2] [3]
Lithium-cyanide-unit-cell-3D-SF.png
Lithium-3D.png
Cyanide-ion-3D-vdW.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.554 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-308-3
PubChem CID
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
AppearanceWhite 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]
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
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.svgHealth 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.

Contents

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

Related Research Articles

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In chemistry, a cyanide is a chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">Gilman reagent</span> Class of chemical compounds

A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an alkyl or aryl. These reagents are useful because, unlike related Grignard reagents and organolithium reagents, they react with organic halides to replace the halide group with an R group (the Corey–House reaction). Such displacement reactions allow for the synthesis of complex products from simple building blocks.

<span class="mw-page-title-main">Cyanohydrin</span> Functional group in organic chemistry

In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:

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<span class="mw-page-title-main">Choline chloride</span> Chemical compound

Choline chloride is an organic compound with the formula [(CH3)3NCH2CH2OH]+Cl. It is a quaternary ammonium salt, consisting of choline cations and chloride anions. It is bifunctional compound, meaning, it contains both quaternary ammonium functional group and a hydroxyl functional group. The cation of this salt, choline, occurs in nature in living beings. Choline chloride is a white, water-soluble salt used mainly in animal feed.

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<span class="mw-page-title-main">Hydrazines</span> Class of chemical compounds

Hydrazines (R2N−NR2) are a class of chemical compounds with two nitrogen atoms linked via a covalent bond and which carry from one up to four alkyl or aryl substituents. Hydrazines can be considered as derivatives of the inorganic hydrazine (H2N−NH2), in which one or more hydrogen atoms have been replaced by hydrocarbon groups.

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<span class="mw-page-title-main">Lithium bis(trimethylsilyl)amide</span> Chemical compound

Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si(CH3)3)2. It is commonly abbreviated as LiHMDS or Li(HMDS) (lithium hexamethyldisilazide - a reference to its conjugate acid HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.

<span class="mw-page-title-main">Thiophosphoryl chloride</span> Chemical compound

Thiophosphoryl chloride is an inorganic compound with the chemical formula PSCl3. It is a colorless pungent smelling liquid that fumes in air. It is synthesized from phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides.

<span class="mw-page-title-main">Hexachlorobutadiene</span> Chemical compound

Hexachlorobutadiene, (often abbreviated as "HCBD") Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds. Structurally, it has a 1,3-butadiene core, but fully substituted with chlorine atoms.

<i>tert</i>-Butyl hydroperoxide Chemical compound

tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, for example the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, tert-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable.

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Neohexene is the hydrocarbon compound with the chemical formula (CH3)3CCH=CH2. It is a colorless liquid, with properties similar to other hexenes. It is a precursor to commercial synthetic musk perfumes.

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. Elsevier. 28 (36): 4189–4190. doi:10.1016/S0040-4039(00)95575-8.