Cyanamide

Related reactions exploit the bifunctionality of cyanamide to give heterocycles, and this latter reactivity is the basis of several pharmaceutical syntheses such as the aminopyrimidine imatinib, and agrichemicals Amitrol and hexazinone.

The hair-loss treatment minoxidil and the anthelmintics albendazole, flubendazole, and mebendazole feature 2-aminoimidazole substructures derived from cyanamide.

The addition product is converted by bases to N-Cyanaziridine,[6] cyclized in the presence of acids to imidazolines, which can be further reacted to vicinal diamines by alkaline cleavage.

[10] Sodium dicyanamide is available in good yield and high purity from cyanamid and cyanogen chloride,[11][12] which is suitable as an intermediate for the synthesis of active pharmaceutical ingredients.

Due to the strong affinity towards self-condensation in alkaline media (see above) solutions of cyanamide are stabilized by the addition of 0.5 wt% of monosodium phosphate as buffer.

Solid cyanamide is produced by careful evaporation of the solvent and subsequent addition of a hydrolysis-labile ester of formic acid.

The ester absorbs traces of moisture (suppression of urea formation), neutralizes alkalinity (ammonia) and continually releases small amounts of formic acid.

[15] Cyanamide, under the trade name Dormex, is a common agricultural rest-breaking agent applied in spring to stimulate uniform opening of buds, early foliation and bloom.

Cyanamide can effectively compensate for the moderate lack of chilling units accumulated in the previous autumn and save the harvest that would otherwise be lost.

A 50% aqueous solution of cyanamide is also used as a biocide (disinfectant) particularly in pig farming, because it effectively kills salmonella and shigella and fights flies in all stages of development.

One example is naphthylcyanamide, C10H7N(CH3)CN, which has been produced by the von Braun reaction,[19] a general method for the conversion of tertiary amines to cyanamides using cyanogen bromide as reagent.

[21]: 1393–1395, 1399 Due to its high permanent dipole moment (i.e., 4.32 ± 0.08 D),[22] cyanamide was detected in spectral emissions coming from the Sgr B2 molecular cloud (T < 100 K) through its microwave transitions as the first known interstellar molecule containing the NCN frame.

Full skeletal formulas of cyanamide, both tautomers
Space-filling model of the cyanamide molecule, nitrile tautomer
Space-filling model of the cyanamide molecule, diimide tautomer
NFPA 704 four-colored diamond Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazards (white): no code
reaction equation
reaction equation