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164011

Sigma-Aldrich

Methyl 3-chloro-3-oxopropionate

97%

Synonym(s):

Methyl malonyl chloride, Methyl chloroformylacetate

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About This Item

Linear Formula:
CH3OCOCH2COCl
CAS Number:
37517-81-0
Molecular Weight:
136.53
Beilstein:
1754078
EC Number:
253-540-6
MDL number:
MFCD00013657
UNSPSC Code:
12352100
PubChem Substance ID:
24850046
NACRES:
NA.22

Quality Level

200

Assay

97%

refractive index

n20/D 1.432 (lit.)

bp

57-59 °C/12 mmHg (lit.)

density

1.273 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(=O)CC(Cl)=O

InChI

1S/C4H5ClO3/c1-8-4(7)2-3(5)6/h2H2,1H3

InChI key

UTBCRHAMJFMIIR-UHFFFAOYSA-N

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General description

Methyl 3-chloro-3-oxopropionate reacts with 4-cyano-1,1′-biphenyl derivatives bearing ω-hydroxyalkyl substituents to yield liquid-crystalline linear malonates and cyanoacetates.

Application

Methyl 3-chloro-3-oxopropionate was used as a reagent in the synthesis of resin-bound 4-tosyl quinolinone, 1-anthracen-9-ylmethyl 3-methyl 2,2-dimethylmalonate and 1-(4-(3,5-dihydropyren-1-yl)butyl)-3-methyl 2,2-dimethylmalonate.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

176.0 °F

Flash Point(C)

80 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Solvent-free microwave-assisted Bingel reaction in carbon nanohorns.
Economopoulos SP, et al.
Journal of Materials Chemistry, 19(39), 7326-7331 (2009)
A general solid phase synthesis of 4-substituted quinolinones via Pd-catalyzed cross coupling.
Xu C, et al.
Tetrahedron Letters, 47(28), 4885-4888 (3006)
Katharina C Kress et al.
Beilstein journal of organic chemistry, 8, 371-378 (2012-04-18)
4-Cyano-1,1'-biphenyl derivatives bearing ω-hydroxyalkyl substituents were reacted with methyl 3-chloro-3-oxopropionate or cyanoacetic acid, giving liquid-crystalline linear malonates and cyanoacetates. These compounds formed monotropic nematic phases at 62 °C down to ambient temperature upon cooling from the isotropic liquid. The mesomorphic

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