Cyanamide

Cyanamide is a type of organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also an intermediate in the biuret and melamine syntheses.

Structure and Synthesis

Cyanamide exists as two tautomers, one with the connectivity NCNH2 and the other with the formula HNCNH. The NCNH2 form dominates, but in a few reactions the diimide form appears to be important.

Cyanamide is produced by hydrolysis of calcium cyanamide, a material that is generated from calcium carbide. The conversion commences with nucleophilic attack of hydroxide on the carbon, followed by proton transfer: CaCN2 + H2O → CaCO3 + H2NCN

Applications

Cyanamide is used in agriculture as a fertilizer and a pesticide. In the form of its calcium salt, it is used as a defoliant.

In organic synthesis, cyanamide is employed as a source of amino functionality, often via addition to carbonyl compounds. For example, it is used to prepare guanidine, dicyandiamide, imidazole, thiourea and urea.

Safety

Cyanamide has a modest toxicity in humans. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

See also

• Calcium cyanamide
• Dicyandiamide
• Guanidine
• Imidazole
• Thiourea
• Urea

References

Cyanamide Resources
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