cyanamides

Cyanamides are a class of chemical compounds that feature the cyanamide functional group, -NH-CN. The simplest member is cyanamide (NH2-CN). In substituted cyanamides, the amino hydrogen is replaced by carbon-based groups, giving structures such as R-NH-CN; the term cyanamide is sometimes used broadly to describe this family.

Properties and reactivity: The cyanamide group combines an amide-type nitrogen with a terminal nitrile. Cyanamides are typically reactive toward hydrolysis, producing ureas or guanidines under basic or acidic conditions, and they can undergo reactions at the nitrile carbon or at nitrogen. Physical properties vary with substituents, and many cyanamides are reactive liquids or solids at room temperature.

Production and uses: In industry, N-substituted cyanamides are usually prepared by the reaction of amines with cyanogen chloride (ClCN). Cyanamides and their derivatives are used as intermediates in organic synthesis, especially in the preparation of guanidines, amidines, and various heterocycles; they also appear in polymer chemistry as monomers or reagents.

Safety: Cyanamide compounds can be irritants and some derivatives may release toxic gases under certain conditions. They should be handled with appropriate protective equipment, and exposure to skin or inhalation should be avoided.

See also: cyanamide, calcium cyanamide, guanidines, dicyandiamide.