2696. 1-Cyanoimidazole

Nomenclature

CAS number: 36289-36-8
1H-Imidazole-1-carbonitrile; N-cyanoimidazole.
C4H3N3; mol wt 93.09.
C 51.61%, H 3.25%, N 45.14%.

Description and references

Coupling and cyanating agent. Prepn: H. Giesemann, J. Prakt. Chem. 4(1), 345 (1955); by thermolysis of tetrazolopyrazine: C. Wentrup, Helv. Chim. Acta 55, 565 (1972); P. B. W. McCallum et al., Aust. J. Chem. 52, 159 (1999). Use as a condensing agent: J. P. Ferris et al., Nucleosides Nucleotides 8, 407 (1989); K. J. Luebke, P. B. Dervan, J. Am. Chem. Soc. 113, 7447 (1991); as a cyanating agent: Y. Wu et al., Org. Lett. 2, 795 (2000).

Chemical structure

Properties

White hygroscopic needles, mp 59.5-60.5°. bp760 185-189°; bp27 95°.

Use

In chemical synthesis as a cyanating agent; as condensing agent in DNA ligation.