Methyl chloroformate

Not to be confused with Methyl chloroform.
Methyl chloroformate[1]
Skeletal formula of methyl chloroformate
Ball-and-stick model of the methyl chloroformate molecule
Names
Preferred IUPAC name
Methyl carbonochloridate
Other names
Methyl chloroformate, Chlorocarbonic methyl ester, Methyl chlorocarbonate
Identifiers
3D model (JSmol)
605437
ChemSpider
ECHA InfoCard 100.001.080 Edit this at Wikidata
EC Number
  • 201-187-3
UNII
  • InChI=1S/C2H3ClO2/c1-5-2(3)4/h1H3 checkY
    Key: XMJHPCRAQCTCFT-UHFFFAOYSA-N checkY
  • InChI=1/C2H3ClO2/c1-5-2(3)4/h1H3
    Key: XMJHPCRAQCTCFT-UHFFFAOYAT
  • O=C(Cl)OC
  • ClC(=O)OC
Properties
ClC(O)OCH3
Molar mass 94.49 g·mol−1
Appearance Colorless oily liquid
Odor Pungent
Density 1.223 g/mL
Boiling point 70 to 72 °C (158 to 162 °F; 343 to 345 K)
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: Toxic
Danger
H225, H302, H312, H314, H330
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501
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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Methyl chloroformate is a chemical compound with the chemical formula Cl−C(=O)−O−CH3. It 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.

Preparation

Methyl chloroformate can be synthesized using anhydrous methanol and phosgene.[2]

COCl2 + CH3OH → ClC(O)OCH3 + HCl

Properties

Methyl chloroformate hydrolyzes in water to form methanol, hydrochloric acid, and carbon dioxide.[3] 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.[4]

Uses

Methyl chloroformate is used in organic synthesis for the introduction of the methoxycarbonyl functionality to a suitable nucleophile (i.e. carbomethoxylation).[5]

Safety

Methyl chloroformate forms highly flammable vapour-air mixtures. The compound has a flash point of 10 °C.[6] 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

References

  1. ^ Methyl chloroformate at Sigma-Aldrich
  2. ^ Siegfried Böhm, Maren Beth-Hübner: Chloroformic Esters. In: Ullmann’s Encyclopedia of Industrial Chemistry. Wiley‐VCH Verlag GmbH & Co. KGaA., 15. April 2006, doi:10.1002/14356007.a06_559.pub2.
  3. ^ "Toxokologische Bewertungen" [Toxicological Information] (PDF) (in German). Retrieved 2021-10-03.
  4. ^ "Methylchlorformiat". GESTIS-Stoffdatenbank (in German). Retrieved 2021-10-03.
  5. ^ Fischer, Emil (1914). "Synthesis of depsides, lichen-substances and tannins". Journal of the American Chemical Society. 36 (6): 1170–1201. doi:10.1021/ja02183a009.
  6. ^ E. Brandes, W. Möller: Sicherheitstechnische Kenngrößen. Band 1: Brennbare Flüssigkeiten und Gase. Wirtschaftsverlag NW – Verlag für neue Wissenschaft, Bremerhaven 2003.

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