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Merck

M35304

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24896852
EC Number:
201-187-3
Beilstein/REAXYS Number:
605437
MDL number:
MFCD00000639
Assay:
99%

Key Documents

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InChI

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

InChI key

XMJHPCRAQCTCFT-UHFFFAOYSA-N

SMILES string

COC(Cl)=O

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

Quality Level

200

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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.

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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

WGK 2

flash_point_f

50.0 °F - closed cup

flash_point_c

10 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB3204
STBL0805
STBK0604
STBJ8556
STBJ5986

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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
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)
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)
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