Methyl chloroformate

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Methyl chloroformate[1]
Skeletal formula of methyl chloroformate
Ball-and-stick model of the methyl chloroformate molecule
Names
IUPAC name
Methyl carbonochloridate
Other names
Methyl chloroformate, Chlorocarbonic methyl ester, Methyl chlorocarbonate
Identifiers
3D model (JSmol)
605437
ChemSpider
ECHA InfoCard 100.001.080
EC Number 201-187-3
Properties
C2H3ClO2
Molar mass 94.49 g·mol−1
Density 1.223 g/mL
Boiling point 70 to 72 °C (158 to 162 °F; 343 to 345 K)
Hazards
Corrosive CDangerous for the Environment (Nature) NHarmful Xn
R-phrases (outdated) R34 R50/53
S-phrases (outdated) (S1/2) S26 S45 S60 S61
Flash point 10 °C (50 °F; 283 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methyl chloroformate is the methyl ester of chloroformic acid and is an oily liquid with a color that is anywhere from yellow to colorless. It is also known for its pungent odor.

Uses[edit]

Methyl chloroformate is used in organic synthesis for the introduction of the methoxycarbonyl functionality to a suitable nucleophile (i.e. carbomethoxylation).[2]

Safety[edit]

Methyl chloroformate, if heated, releases phosgene and produces toxic, corrosive fumes if it comes in contact with water.

See also[edit]

References[edit]

  1. ^ Methyl chloroformate at Sigma-Aldrich
  2. ^ Fischer, Emil (1914). "Synthesis of depsides, lichen-substances and tannins". Journal of the American Chemical Society. 36 (6): 1170–1201. doi:10.1021/ja02183a009.