M35304
Methyl chloroformate
99%
Synonym(s):
MCF, Chloroformic acid methyl ester
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About This Item
Linear Formula:
ClCOOCH3
CAS Number:
Molecular Weight:
94.50
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-187-3
Beilstein/REAXYS Number:
605437
MDL number:
Assay:
99%
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
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:
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
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
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)