A carbamoyl chloride is the

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

with the formula R₂NC(O)Cl. The parent carbamoyl chloride, H₂NCOCl is unstable, but many N-substituted analogues are known. Most examples are moisture sensitive, colourless, and soluble in nonpolar organic solvents. An example is dimethylcarbamoyl chloride (m.p. −90 °C and b.p. 93 °C). Carbamoyl chlorides are used to prepare a number of pesticides, e.g.

carbofuran Carbofuran is a carbamate pesticide, widely used around the world to control insects on a wide variety of field crops, including potatoes, corn and soybeans. It is a systemic insecticide, which means that the plant absorbs it through the roots ...

and

aldicarb Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a choli ...

Production and examples

Carbamoyl chlorides are prepared by the reaction of an amine with phosgene: :2 R₂NH + COCl₂ → R₂NCOCl + ₂NH₂l They also arise by the addition of

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride g ...

isocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...

s: :RNCO + HCl → RNHCOCl In this way, carbamonyl chlorides can be prepared with N-H functionality.

Reactions

In a reaction that is typically avoided, hydrolysis of carbamoyl chlorides gives

carbamic acid Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula . It can be obtained by the reaction of ammonia and carbon dioxide at very low temperatures, which also yields an ...

s: :R₂NCOCl + H₂O → R₂NC(O)OH + HCl Owing to the influence of the amino group, these compounds are less hydrolytically sensitive than the usual

acid chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

s. A related but more useful reaction is the analogous reaction with alcohols:{{cite journal, authors=Carol Dallaire, Isabelle Kolber, and Marc Gingras, title=Nickel-Catalyzed Coupling of Aryl O-Carbamates with Grignard Reagents: 2,7-Dimethylnaphthalene, journal=Org. Synth., year=2002, volume=78, pages=42, doi=10.15227/orgsyn.078.0042). Notes: describes use of diethylcarbamoyl chloride as protecting and leaving group. :R₂NCOCl + R'OH + C₅H₅N → R₂NC(O)OR' + C₅H₅NHCl

References

Functional groups