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M35304

Sigma-Aldrich

Methyl chloroformate

99%

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Synonym(s):
MCF, Chloroformic acid methyl ester
Linear Formula:
ClCOOCH3
CAS Number:
Molecular Weight:
94.50
Beilstein/REAXYS Number:
605437
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.26 (vs air)

Quality Level

vapor pressure

4.8 psi ( 20 °C)

assay

99%

autoignition temp.

905 °F

refractive index

n20/D 1.387 (lit.)

bp

70-72 °C (lit.)

density

1.223 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(Cl)=O

InChI

1S/C2H3ClO2/c1-5-2(3)4/h1H3

InChI key

XMJHPCRAQCTCFT-UHFFFAOYSA-N

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1 of 4

This Item
672106671673669695
vibrant-m

M35304

Methyl chloroformate

vibrant-m

672106

Methyl 3-(chlorocarbonyl)benzoate

vibrant-m

671673

Methyl 4-(chlorocarbonyl)benzoate

vibrant-m

669695

Ethyl fumaroyl chloride

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

bp

70-72 °C (lit.)

bp

-

bp

-

bp

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

refractive index

n20/D 1.387 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.463

density

1.223 g/mL at 25 °C (lit.)

density

-

density

-

density

-

Application

Methyl chloroformate (MCF) is generally used for the derivatization of functional groups such as carboxylic acids, amines, and phenols.
MCF can also be used:
  • To activate 3-acylpyridines for nucleophilic addition with alkynyltin reagents to form 2,3-disubstituted 1,2-dihydropyridines.
  • Chloroesterification of terminal alkynes to form β-chloro-α,β-unsaturated esters.
  • As an electrophilic reagent to mediate the reaction of pyridine with lithium dialkyl- or diarylcuprates to form 4-substituted 1,4-dihydropyridine derivatives.
  • To convert nitronates into methoxycarbonyl nitronates.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

50.0 °F - closed cup

flash_point_c

10 °C - closed cup


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