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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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)
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)
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