Ammonium cyanide

Ammonium cyanide is an unstable inorganic compound with the chemical formula NH₄CN. It is the ammonium salt of hydrogen cyanide. It consists of ammonium cations NH+4 and cyanide anions CN⁻. Its structural formula is [NH₄]⁺[C≡N]⁻.

Ammonium cyanide

Identifiers
CAS Number	12211-52-8 Y
3D model (JSmol)	Interactive image
ChemSpider	140210 Y
PubChem CID	159440
UNII	898Y75UR3N Y
CompTox Dashboard (EPA)	DTXSID00153500
InChI InChI=1S/CN.H3N/c1-2;/h;1H3/q-1;/p+1 Y Key: ICAIHGOJRDCMHE-UHFFFAOYSA-O Y InChI=1/CN.H3N/c1-2;/h;1H3/q-1;/p+1 Key: ICAIHGOJRDCMHE-IKLDFBCSAW
SMILES [C-]#N.[NH4+]
Properties
Chemical formula	[NH4]CN
Molar mass	44.0559 g/mol
Appearance	colourless crystalline solid
Density	1.02 g/cm3
Melting point	36 °C (decomp.)
Solubility in water	very soluble
Solubility	very soluble in alcohol
Structure
Crystal structure	cubic
Related compounds
Other anions	Ammonium hydroxide Ammonium azide Ammonium nitrate
Other cations	Sodium cyanide Potassium cyanide
Related compounds	Ammonia Hydrogen cyanide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Uses

Ammonium cyanide is generally used in organic synthesis.^{[citation needed]} Being unstable, it is not shipped or sold commercially.

Preparation

Ammonium cyanide is prepared by combining solutions of hydrogen cyanide and ammonia:^{[citation needed]}

HCN + NH₃ → NH₄CN

It may be prepared by the reaction of calcium cyanide and ammonium carbonate:^{[citation needed]}

Ca(CN)₂ + (NH₄)₂CO₃ → 2 NH₄CN + CaCO₃

In dry state, ammonium cyanide is made by heating a mixture of potassium cyanide or potassium ferrocyanide with ammonium chloride and condensing the vapours into ammonium cyanide crystals:^{[citation needed]}

KCN + NH₄Cl → NH₄CN + KCl

Reactions

Ammonium cyanide decomposes to ammonia and hydrogen cyanide, often forming a black polymer of hydrogen cyanide:^[1]

NH₄CN → NH₃ + HCN

It undergoes salt metathesis reaction in solution with a number of metal salts to form metal–cyanide complexes.

Reaction with ketones and aldehydes yield aminonitriles, as in the first step of the Strecker amino acid synthesis:

NH₄CN + (CH₃)₂CO → (CH₃)₂C(NH₂)CN + H₂O

Toxicity

Further information: Cyanide poisoning

Ammonium cyanide is highly toxic.