163872

Sigma-Aldrich

Ethyl malonyl chloride

technical grade

Synonym(s):
Ethyl (chloroformyl)acetate, Ethyl 3-chloro-3-oxopropionate
Linear Formula:
CH3CH2OCOCH2COCl
CAS Number:
Molecular Weight:
150.56
Beilstein/REAXYS Number:
636215
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

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.

Packaging

5, 25 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3265 8 / PGIII

WGK Germany

WGK 3

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

Synthesis, 2019-2019 (2006)
J T Gau et al.
Cancer research, 57(17), 3830-3834 (1997-09-01)
Prostate-specific antigen (PSA) has been demonstrated to release the active form of insulin-like growth factor I in vitro (P. Cohen et al., J. Clin. Endocrinol. & Metab., 75: 1046-1053, 1992; P. Cohen et al., J. Clin. Endocrinol. & Metab., 79:...
Synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazoles as peptidomimetic building blocks.
Jakopin Z, et al.
Tetrahedron Letters, 48(8), 1465-1468 (2007)
Synlett, 65-65 (1993)
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...

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