Methyl chloroformate

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.

Methyl chloroformate[1]

Names
IUPAC name Methyl carbonochloridate
Other names Methyl chloroformate, Chlorocarbonic methyl ester, Methyl chlorocarbonate
Identifiers
CAS Number	79-22-1^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	605437
ChemSpider	6337^Y
ECHA InfoCard	100.001.080
EC Number	201-187-3
PubChem CID	6586
UNII	RC6VA8OB2N^Y
CompTox Dashboard (EPA)	DTXSID0024185
InChI InChI=1S/C2H3ClO2/c1-5-2(3)4/h1H3^Y Key: XMJHPCRAQCTCFT-UHFFFAOYSA-N^Y 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
EU classification (DSD) (outdated)	C N Xn
R-phrases (outdated)	R34 R50/53
S-phrases (outdated)	(S1/2) S26 S45 S60 S61
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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Infobox references

Preparation

Methyl chloroformate can be synthesized using methanol and phosgene.

${\displaystyle {\ce {COCl2 + MeOH-> C2H3ClO2 + HCl}}}$

Uses

Methyl chloroformate is used in organic synthesis for the introduction of the methoxycarbonyl functionality to a suitable nucleophile (i.e. carbomethoxylation).[2]

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

• Ethyl chloroacetate
• Chloroacetic acid

References

1. Methyl chloroformate at Sigma-Aldrich
2. Fischer, Emil (1914). "Synthesis of depsides, lichen-substances and tannins". Journal of the American Chemical Society. 36 (6): 1170–1201. doi:10.1021/ja02183a009.