Methyl chloroformate explained

Methyl chloroformate should not be confused with Methyl chloroform.

Methyl chloroformate is a chemical compound with the chemical formula . 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.[1]

Properties

Methyl chloroformate hydrolyzes in water to form methanol, hydrochloric acid, and carbon dioxide.[2] 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.[3]

Uses

Methyl chloroformate is used in organic synthesis for the introduction of the methoxycarbonyl functionality to a suitable nucleophile (i.e. carbomethoxylation).[4]

Safety

Methyl chloroformate forms highly flammable vapour-air mixtures. The compound has a flash point of 10 °C.[5] 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

Notes and References

  1. Siegfried Böhm, Maren Beth-Hübner: Chloroformic Esters. In: Ullmann’s Encyclopedia of Industrial Chemistry. Wiley‐VCH Verlag GmbH & Co. KGaA., 15. April 2006, .
  2. Web site: Toxokologische Bewertungen. Toxicological Information. 2021-10-03. de.
  3. Web site: Methylchlorformiat. 2021-10-03. GESTIS-Stoffdatenbank. de.
  4. Fischer. Emil. Synthesis of depsides, lichen-substances and tannins. Journal of the American Chemical Society. 1914. 36. 6. 1170–1201. 10.1021/ja02183a009.
  5. E. Brandes, W. Möller: Sicherheitstechnische Kenngrößen. Band 1: Brennbare Flüssigkeiten und Gase. Wirtschaftsverlag NW – Verlag für neue Wissenschaft, Bremerhaven 2003.