Cyanogen Azide

Title: Cyanogen Azide
CAS Registry Number: 764-05-6
Additional Names: Carbon pernitride
Molecular Formula: CN4
Molecular Weight: 68.04
Percent Composition: C 17.65%, N 82.34%
Literature 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).
Properties: Clear, colorless, oily liquid. Caution: 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).
Cyanogen Bromide Cyanogen Chloride Cyanogen Iodide Cyanopsin Cyanuric Acid