M35304

Sigma-Aldrich

Methyl chloroformate

99%

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

Quality Level

vapor density

3.26 (vs air)

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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Related Categories

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.

Packaging

100, 500 g in Sure/Seal™
5 g in glass bottle

Signal Word

Danger

hazcat

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 Germany

WGK 2

Flash Point(F)

50.0 °F - closed cup

Flash Point(C)

10 °C - closed cup

Certificate of Analysis

Certificate of Origin

Regio-and chemoselective addition of alkynyltin reagents to the 2-position of 3-acylpyridines activated by methyl chloroformate: selective synthesis of 2, 3-disubstituted 1, 2-dihydropyridines.
Yamaguchi R, et al.
Tetrahedron Letters, 29(15), 1785-1788 (1988)
The First Example of Rhodium (I)-Catalyzed Regio-and Stereoselective Chloroesterification of Alkynes with Chloroformate Esters.
Hua R, et al.
Journal of the American Chemical Society, 120(47), 12365-12366 (1998)
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...
Francesca Casu et al.
Metabolomics : Official journal of the Metabolomic Society, 14(8), 103-103 (2019-03-05)
Saccharomyces cerevisiae has been widely used for fermenting food and beverages for over thousands years. Its metabolism together with the substrate composition play an important role in determining the characteristics of the final fermented products. We previously showed that the...
Amrei Windelberg et al.
Clinical chemistry, 51(11), 2103-2109 (2005-08-27)
The combined measurement of methylmalonic acid (MMA) and total homocysteine (tHcy) in serum or plasma is useful in diagnosing and distinguishing between cobalamin and folate deficiencies. We developed and validated an isotope-dilution gas chromatography-mass spectrometry (GC-MS) method with automated sample...

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