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163872

Sigma-Aldrich

Ethyl malonyl chloride

technical grade

Synonym(s):

Ethyl (chloroformyl)acetate, Ethyl 3-chloro-3-oxopropionate

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About This Item

Linear Formula:
CH3CH2OCOCH2COCl
CAS Number:
36239-09-5
Molecular Weight:
150.56
Beilstein:
636215
EC Number:
252-934-5
MDL number:
MFCD00000736
UNSPSC Code:
12352100
PubChem Substance ID:
24850040
NACRES:
NA.22

grade

technical grade

Quality Level

200

refractive index

n20/D 1.429 (lit.)

bp

79-80 °C/25 mmHg (lit.)

density

1.176 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)CC(Cl)=O

InChI

1S/C5H7ClO3/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3

InChI key

KWFADUNOPOSMIJ-UHFFFAOYSA-N

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General description

Ethyl malonyl chloride is a versatile acylating agent for propargyl alcohols, hydrazines and amines.

Application

Ethyl malonyl chloride was used in the synthesis of:
  • liquid-crystalline methanofullerodendrimers
  • 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks
  • 3-pyrrolin-2-ones via amidation with propargylamines and subsequent base catalyzed 5-exo-dig cyclization
Versatile acylating agent for propargyl alcohols, hydrazines, and amines.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sudarat Yenjai et al.
Journal of photochemistry and photobiology. B, Biology, 186, 23-30 (2018-07-11)
Rational design of photoreagents with systematic modifications of their structures can provide valuable information for a better understanding of the protein photocleavage mechanism by these reagents. Variation of the length of the linker connecting the photoactive moiety with the protein
Liquid-crystalline methanofullerodendrimers which display columnar mesomorphism.
Maringa N, et al.
Journal of Materials Chemistry, 18(13), 1524-1534 (2008)
N A Meanwell et al.
Journal of medicinal chemistry, 36(24), 3871-3883 (1993-11-26)
The 4,5-diphenyloxazole derivatives 2-4 were previously identified as nonprostanoid prostacyclin (PGI2) mimetics. A series of derivatives of 2-4 bearing substitutents at the carbon atom alpha to the oxazole ring were synthesized and evaluated as inhibitors of ADP-induced aggregation of human
Synlett, 65-65 (1993)
Synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazoles as peptidomimetic building blocks.
Jakopin Z, et al.
Tetrahedron Letters, 48(8), 1465-1468 (2007)
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