2692. Cyanogen Azide

Nomenclature

CAS number: 764-05-6
Carbon pernitride.
CN4; mol wt 68.04.
C 17.65%, N 82.34%.

Description and references

Prepd by suspending NaN3 in dry acetonitrile and distilling cyanogen chloride into the cooled suspension: Marsh, Hermes, J. Am. Chem. Soc. 86, 4506 (1964); see also Chem. Eng. News 42, 51 (Oct. 26, 1964); Marsh, US 3410658 (1968); Marsh, J. Org. Chem. 37, 2966 (1972). Spectrum, structure, dipole moment: Costain, Kroto, Can. J. Phys. 50, 1453 (1972); Almenningen et al., Acta Chem. Scand. 27, 1531 (1973).

Chemical structure

Properties

Clear, colorless, oily liquid. The pure azide detonates violently upon thermal, electrical or mechanical shock. Can be handled relatively safely in solvents. Half-life of a 27% soln in acetonitrile is 15 days at room temp, more stable at lower temps.

Use

In organic synthesis. Has a versatility and scope of chemical reactivity that is very broad and useful, e.g. reacts with alkanes to give primary alkylcyanamides: Anastassiou et al., J. Am. Chem. Soc. 87, 2296 (1965).