Methyl chloroformate is the

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor.

Preparation

Methyl chloroformate can be synthesized using

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...

and

phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, esp ...

. COCl2 + MeOH-> C2H3ClO2 + HCl

Properties

Methyl chloroformate hydrolyzes in water to form

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid. It is a component of the gastric acid in the dige ...

, and

carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is t ...

. This decomposition happens violently in the presence of steam, causing foaming. The compound decomposes in heat, which can liberate hydrogen chloride, phosgene, chlorine, or other toxic gases.

Uses

Methyl chloroformate is used in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

for the introduction of the methoxycarbonyl functionality to a suitable

nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they ar ...

(i.e. carbomethoxylation).

Safety

Methyl chloroformate, if heated, releases phosgene. It produces hydrogen chloride upon contact with water. It will cause skin damage if in contact with skin.

References

{{reflist Methyl esters Chloroformates Reagents for organic chemistry

Preparation

Properties

Uses

Safety

See also

References