Lithium cyanide

Lithium cyanide[1][2][3]
Identifiers
CAS Number	2408-36-8;
3D model (JSmol)	Interactive image;
ChemSpider	68007;
ECHA InfoCard	100.017.554
PubChem CID	75478;
UN number	1935
CompTox Dashboard (EPA)	DTXSID10946920 ;
	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 colored
Boiling point	N/A
Solubility in water	Soluble
Henry's law; constant (kH)	N/A
Structure
Crystal structure	-
Coordination geometry	Fourfold
Hazards
Safety data sheet	742899
EU classification (DSD) (outdated)	T+, Very Toxic N, Dangerous for the environment
R-phrases (outdated)	26/27/28-32-50/53
S-phrases (outdated)	7-28-29-45-60-61
NFPA 704 (fire diamond)	0 4 1
Flash point	57 °C (135 °F; 330 K)
Autoignition; temperature	N/A
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

Lithium cyanide is an inorganic compound with the chemical formula LiCN. It is a toxic, white colored, hygroscopic, water-soluble salt that finds only niche uses.

Preparation

LiCN arises from the interaction of lithium hydroxide and hydrogen cyanide. A laboratory-scale preparation uses acetone cyanohydrin as a surrogate for HCN: [4]

(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.[5]

Lithium cyanide can be used as a reagent for organic compound cyanation.[6]

RX + LiCN → RCN

References

J. A. Lely, J. M. Bijvoet (1942), "The Crystal Structure of Lithium Cyanide", Recueil des Travaux Chimiques des Pays-Bas, 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
Material Safety Data Sheet: Lithium Cyanide, 0.5M Solution in N,N-Dimethylformamide, Fisher Scientific, 16 June 1999
Tom Livinghouse (1981). "Trimethylsilyl Cyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10.15227/orgsyn.060.0126.CS1 maint: uses authors parameter (link)
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. Elsevier. 28 (36): 4189–4190. doi:10.1016/S0040-4039(00)95575-8.

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[1] J. A. Lely, J. M. Bijvoet (1942), "The Crystal Structure of Lithium Cyanide", Recueil des Travaux Chimiques des Pays-Bas, 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

[3] Material Safety Data Sheet: Lithium Cyanide, 0.5M Solution in N,N-Dimethylformamide, Fisher Scientific, 16 June 1999

[4] Tom Livinghouse (1981). "Trimethylsilyl Cyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10.15227/orgsyn.060.0126.CS1 maint: uses authors parameter (link)

[wiley1-5] 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.

[6] 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.

Lithium compounds
Inorganic	Li₂ LiB(C₆F₅)₄ LiCF₃SO₃ LiCH₃O LiAlCl₄ LiAlH₄ LiAlO₂ LiBF₄ LiBH₄ LiBO₂ LiB₃O₅ Li₂B₄O₇ LiBr LiCN Li₂CO₃ Li₂C₂ LiCl LiClO LiClO₃ LiClO₄ LiCoO₂ LiF LiGaH₄ LiH LiHe LiHCO₃ LiI LiIO₃ Li₂IrO₃ Li₂MoO₄ LiNH₂ Li₂NH LiN₃ Li₃N LiNO₂ LiNO₃ LiNbO₃ LiO⁻ LiOH LiO₂ Li₂O Li₂O₂ LiPF₆ Li₂PtO₃ Li₂Po Li₂RuO₃ Li₂S Li₂SO₃ Li₂SO₄ Li₃H(CO₃)₂ Li₂SiO₃ Li₂Si₂O₅ LiTaO₃ Li₂TiO₃
Organic	Methyllithium CH₃Li tert-Butyllithium (CH₃)₃CLi Lithium cyclopentadienide C₅H₅Li Neopentyllithium C₅H₁₁Li Lithium diphenylphosphide (C₆H₅)₂PLi Lithium tetramethylpiperidide C₉H₁₈LiN LiTFSI LiC₂F₆NO₄S₂ Superhydride LiEt₃BH LiHMDS LiN(SiMe₃)₂ 12-hydroxystearate C₁₈H₃₅LiO₃ acetate CH₃COOLi aspartate C₄H₆LiNO₄ citrate Li₃C₆H₅O₇ diisopropylamide LiN(C₃H₇)₂ orotate C₅H₃LiN₂O₄ succinate C₄H₅LiO₄ stearate LiO₂C(CH₂)₁₆CH₃ organolithiums n-Butyllithium
Minerals	Amblygonite Elbaite Eucryptite Jadarite Lepidolite Lithiophilite Petalite Pezzottaite Saliotite Spodumene Sugilite Tourmaline Zabuyelite Zinnwaldite
Hypothetical	Lithium beryllide
Miscellaneous	LB buffer

1	2	3	4	5	6	7	8	9	10	11	12	13	14	15	16	17	18
HCN																	He
LiCN	Be(CN) 2											B(CN)₃, B(CN)− 4	C(CN)₄ C₂(CN)₂, C(CN)− 3	NH 4CN, N 3CN, N(CN)− 2	OCN− , -NCO	FCN	Ne
NaCN	Mg(CN) 2											Al(CN) 3, Al(CN)− 4	Si(CN) 4, (CH 3) 3SiCN, Si(CN)2− 6	P(CN) 3	SCN− , -NCS, (SCN) 2, S(CN) 2	ClCN	Ar
KCN	Ca(CN) 2	Sc(CN) 3	Ti(CN)3− 6	V(CN)3− 6	Cr(CN)3− 6, Cr(CN)4− 6, Cr(CN)6− 6	Mn(CN)4− 6, Mn(CN)3− 6, Mn(CN)5− 6	Fe(CN)4− 6, Fe(CN)3− 6	Co(CN) 2, Cr(CN)4− 5, Co(CN)3− 6	Ni(CN) 2 Ni(CN)2− 4 Ni(CN)4− 4, Ni(CN)3− 5	CuCN, Cu(CN)− 2, Cu(CN)3− 4	Zn(CN) 2, Zn(CN)2− 4	Ga(CN) 3	Ge(CN)2− 6	As(CN) 3, (CH 3) 2AsCN	SeCN− (SeCN) 2 Se(CN) 2	BrCN	Kr
RbCN	Sr(CN) 2	Y(CN) 3	Zr	Nb(CN)5− 8, Nb(CN)4− 8	Mo(CN)5− 7, Mo(CN)4− 8, Mo(CN)3− 8	Tc(CN)5− 6, Tc(CN)4− 7	Ru(CN)4− 6, Ru(CN)3− 6	Rh(CN)3− 6	Pd(CN)2− 4, Pt(CN)2− 6	AgCN, Ag(CN)− 2	Cd(CN) 2, Cd(CN)2− 4	In(CN) 3	Sn(CN)2− 6	Sb(CN) 3	Te	ICN	Xe
CsCN	Ba(CN) 2		Hf	Ta(CN)5− 8, Ta(CN)4− 8	W(CN)5− 7, W(CN)4− 8, W(CN)3− 8	Re(CN)5− 6, Re(CN)4− 7	Os(CN)4− 6, Os(CN)3− 6	Ir(CN)3− 6	Pt(CN)2− 4, Pt(CN)4− 6	AuCN, Au(CN)− 2, Au(CN)− 4	Hg 2(CN) 2, Hg(CN) 2, Hg(CN)2− 4	TlCN	Pb(CN) 2	Bi(CN) 3	Po	At	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		La	Ce(CN) 3, Ce(CN) 4	Pr	Nd	Pm	Sm	Eu	Gd(CN) 3	Tb	Dy	Ho	Er	Tm	Yb	Lu
		Ac	Th	Pa	UO 2(CN) 2	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr