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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:
Molecular Weight:
150.56
Beilstein/REAXYS Number:
636215
EC Number:
MDL number:
UNSPSC Code:
12352100
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.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

supp_hazards

wgk_germany

WGK 3

flash_point_f

147.2 °F

flash_point_c

64 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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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Ethylmalonic acid 97%

Sigma-Aldrich

102687

Ethylmalonic acid

Synthesis, 2019-2019 (2006)
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)
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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