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 many ...
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 ar ...
of
chloroformic acid
Chloroformic acid is an unstable chemical compound with the formula ClCO2H. It is the single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative). Chloroformic acid is also structurally related to formic acid, w ...
. 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 a ...
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, espe ...
.
COCl2 + MeOH-> C2H3ClO2 + HCl
Properties
Methyl chloroformate hydrolyzes in water to form
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 a ...
,
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
Acid strength is the tendency of an acid, symbol ...
, 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 transpar ...
. 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 are ...
(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.
See also
*
Ethyl chloroacetate
Ethyl chloroacetate is a chemical compound used primarily in the chemical industry. It is used as a solvent for organic synthesis and as an intermediate in the production of pesticides (such as sodium fluoroacetate
Sodium fluoroacetate is an or ...
*
Chloroacetic acid
Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds ...
References
{{reflist
Methyl esters
Chloroformates
Reagents for organic chemistry