Synthesis of cyanogen azide

Preparation of cyanogen azide

The synthesis of cyanogen azide is carried out by adding cyanogen chloride to sodium azide. Excess cyanogen chloride or anhydrous aprotic solvents may be used as reaction media.

Preparation of cyanogen azide

Preparation of cyanogen azide

Sodium azide was suspended in dry acetonitrile, and cyanogen chloride was distilled into the mixture at a rate to maintain the temperature below 12° C. The solution was allowed to warm to room temperature and filtered to remove sodium chloride. The use of dry solvents is important to avoid the formation of explosive, solid by-products, and care also must be taken to avoid separating cyanogen azide from solution through evaporating low-boiling solvents, cooling saturated solutions, or freezing the solvent.

J. Am. Chem. Soc. (20), 4506–4507, 1964

IUPAC Name

carbononitridic azide

InChI

InChI=1S/CN4/c2-1-4-5-3

InChI Key

KWEDUNSJJZVRKR-UHFFFAOYSA-N

Canonical SMILES

C(#N)N=[N+]=[N-]

Depositor-Supplied Synonyms

Cyanogen azide, carbononitridic azide, 764-05-6, N.equiv.CN3, cyanic azide, AC1Q1UGY, UNII-159Y7EZP9V, 159Y7EZP9V, AC1L38U7, KWEDUNSJJZVRKR-UHFFFAOYSA-N

Removed Synonyms

CID136583

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