Methyl chloroformate

Methyl chloroformate[1]
Names
	Preferred IUPAC name Methyl carbonochloridate
	Other names Methyl chloroformate, Chlorocarbonic methyl ester, Methyl chlorocarbonate
Identifiers
CAS Number	79-22-1 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	605437
ChemSpider	6337 ;
ECHA InfoCard	100.001.080
EC Number	201-187-3;
PubChem CID	6586;
UNII	RC6VA8OB2N ;
CompTox Dashboard (EPA)	DTXSID0024185 ;
	InChI InChI=1S/C2H3ClO2/c1-5-2(3)4/h1H3 Key: XMJHPCRAQCTCFT-UHFFFAOYSA-N ; InChI=1/C2H3ClO2/c1-5-2(3)4/h1H3 Key: XMJHPCRAQCTCFT-UHFFFAOYAT;
	SMILES O=C(Cl)OC; ClC(=O)OC;
Properties
Chemical formula	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:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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 anhydrous methanol and phosgene.[2]

${\ce {COCl2 + MeOH-> MeOC(O)Cl + HCl}}$

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.

References

Methyl chloroformate at Sigma-Aldrich
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.
"Toxokologische Bewertungen" [Toxicological Information] (PDF) (in German). Retrieved 2021-10-03.
"Methylchlorformiat". GESTIS-Stoffdatenbank (in German). Retrieved 2021-10-03.
Fischer, Emil (1914). "Synthesis of depsides, lichen-substances and tannins". Journal of the American Chemical Society. 36 (6): 1170–1201. doi:10.1021/ja02183a009.
E. Brandes, W. Möller: Sicherheitstechnische Kenngrößen. Band 1: Brennbare Flüssigkeiten und Gase. Wirtschaftsverlag NW – Verlag für neue Wissenschaft, Bremerhaven 2003.

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[1] Methyl chloroformate at Sigma-Aldrich

[Ullmann-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.

[Brandes-6] E. Brandes, W. Möller: Sicherheitstechnische Kenngrößen. Band 1: Brennbare Flüssigkeiten und Gase. Wirtschaftsverlag NW – Verlag für neue Wissenschaft, Bremerhaven 2003.