All Photos(1)
Synonym(s):
Ethyl (chloroformyl)acetate, Ethyl 3-chloro-3-oxopropionate
Linear Formula:
CH3CH2OCOCH2COCl
CAS Number:
Molecular Weight:
150.56
Beilstein:
636215
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Supplementary Hazards
WGK
WGK 3
Flash Point(F)
147.2 °F
Flash Point(C)
64 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazoles as peptidomimetic building blocks.
Jakopin Z, et al.
Tetrahedron Letters, 48(8), 1465-1468 (2007)
Synthesis, 2019-2019 (2006)
Synlett, 65-65 (1993)
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:
Liquid-crystalline methanofullerodendrimers which display columnar mesomorphism.
Maringa N, et al.
Journal of Materials Chemistry, 18(13), 1524-1534 (2008)
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