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M35304

Sigma-Aldrich

Methyl chloroformate

99%

Synonym(s):

MCF, Chloroformic acid methyl ester

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About This Item

Linear Formula:
ClCOOCH3
CAS Number:
79-22-1
Molecular Weight:
94.50
Beilstein:
605437
EC Number:
201-187-3
MDL number:
MFCD00000639
UNSPSC Code:
12352100
PubChem Substance ID:
24896852
NACRES:
NA.22

vapor density

3.26 (vs air)

Quality Level

200

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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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.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

50.0 °F - closed cup

Flash Point(C)

10 °C - closed cup

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Kathleen F Smart et al.
Nature protocols, 5(10), 1709-1729 (2010-10-05)
This protocol describes an analytical platform for the analysis of intra- and extracellular metabolites of microbial cells (yeast, filamentous fungi and bacteria) using gas chromatography-mass spectrometry (GC-MS). The protocol is subdivided into sampling, sample preparation, chemical derivatization of metabolites, GC-MS
M G Zampolli et al.
Journal of chromatography. A, 1150(1-2), 162-172 (2007-01-16)
This work describes a GC-MS method for enantioselective separation of amino acids. The method is based on a derivatization reaction which employs a mixture of alkyl chloroformate-alcohol-pyridine, as reagents to obtain the N(O,S)-alkyl alkoxy carbonyl esters of amino acids. Various
Ting-Li Han et al.
PloS one, 8(8), e71364-e71364 (2013-08-21)
Phenylethyl alcohol was one of the first quorum sensing molecules (QSMs) identified in C. albicans. This extracellular signalling molecule inhibits the hyphal formation of C. albicans at high cell density. Little is known, however, about the underlying mechanisms by which
Reaction of Cuprate Reagents with Pyridine in the Presence of Chloroformate. A Novel Synthesis of 1, 4-Dihydropyridine Derivatives.
Piers E and Soucy M
Canadian Journal of Chemistry, 52(20), 3563-3564 (1974)
Using design of experiments to optimize derivatization with methyl chloroformate for quantitative analysis of the aqueous phase from hydrothermal liquefaction of biomass.
Madsen R B, et al.
Analytical and Bioanalytical Chemistry, 408(8), 2171-2183 (2016)
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