Methyl chloroformate

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

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
UNII
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R-phrases (outdated) R34 R50/53
S-phrases (outdated) (S1/2) S26 S45 S60 S61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

PreparationEdit

Methyl chloroformate can be synthesized using methanol and phosgene.

 

UsesEdit

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

SafetyEdit

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 alsoEdit

ReferencesEdit

  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.