Methyl chloroformate
Names | |
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Preferred IUPAC name
Methyl carbonochloridate | |
Other names
Methyl chloroformate, Chlorocarbonic methyl ester, Methyl chlorocarbonate
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Identifiers | |
3D model (JSmol)
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605437 | |
ChemSpider | |
EC Number |
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PubChem CID
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UNII | |
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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 | |
GHS labelling: | |
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 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 methanol and phosgene.
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, 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
- ^ Methyl chloroformate at Sigma-Aldrich
- ^ "Toxokologische Bewertungen" [Toxicological Information] (PDF) (in German). Retrieved 2021-10-03.
{{cite web}}
: CS1 maint: url-status (link) - ^ "Methylchlorformiat". GESTIS-Stoffdatenbank (in German). Retrieved 2021-10-03.
{{cite web}}
: CS1 maint: url-status (link) - ^ Fischer, Emil (1914). "Synthesis of depsides, lichen-substances and tannins". Journal of the American Chemical Society. 36 (6): 1170–1201. doi:10.1021/ja02183a009.
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- Methyl esters
- Chloroformates
- Reagents for organic chemistry