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Methyl chloroformate

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Not to be confused with Methyl chloroform.
Methyl chloroformate
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
CAS Number
3D model (JSmol)
Beilstein Reference 605437
ChemSpider
ECHA InfoCard 100.001.080 Edit this at Wikidata
EC Number
  • 201-187-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H3ClO2/c1-5-2(3)4/h1H3Key: XMJHPCRAQCTCFT-UHFFFAOYSA-N
  • InChI=1/C2H3ClO2/c1-5-2(3)4/h1H3Key: XMJHPCRAQCTCFT-UHFFFAOYAT
SMILES
  • O=C(Cl)OC
  • ClC(=O)OC
Properties
Chemical formula ClC(O)OCH3
Molar mass 94.49 g·mol
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:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS06: Toxic
Signal word Danger
Hazard statements H225, H302, H312, H314, H330
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

COCl2 + CH3OH → ClC(O)OCH3 + HCl

Properties

Methyl chloroformate hydrolyzes in water to form methanol, hydrochloric acid, and carbon dioxide. 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 for the introduction of the methoxycarbonyl functionality to a suitable nucleophile (i.e. carbomethoxylation).

Safety

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