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M35304

Sigma-Aldrich

Methyl chloroformate

99%

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Synonym(s):
MCF, Chloroformic acid methyl ester
Linear Formula:
ClCOOCH3
CAS Number:
Molecular Weight:
94.50
Beilstein:
605437
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

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This Item
672106671673669695
Methyl chloroformate 99%

Sigma-Aldrich

M35304

Methyl chloroformate

refractive index

n20/D 1.387 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.463

bp

70-72 °C (lit.)

bp

-

bp

-

bp

-

density

1.223 g/mL at 25 °C (lit.)

density

-

density

-

density

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

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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Reaction of Cuprate Reagents with Pyridine in the Presence of Chloroformate. A Novel Synthesis of 1, 4-Dihydropyridine Derivatives.
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Canadian Journal of Chemistry, 52(20), 3563-3564 (1974)
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.
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Tetrahedron Letters, 29(15), 1785-1788 (1988)
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