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Merck
CN

163872

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24850040
EC Number:
252-934-5
Beilstein/REAXYS Number:
636215
MDL number:
MFCD00000736

Key Documents

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Product Name

Ethyl malonyl chloride, technical grade

InChI key

KWFADUNOPOSMIJ-UHFFFAOYSA-N

InChI

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

SMILES string

CCOC(=O)CC(Cl)=O

grade

technical grade

refractive index

n20/D 1.429 (lit.)

bp

79-80 °C/25 mmHg (lit.)

density

1.176 g/mL at 25 °C (lit.)

functional group

acyl chloride
ester

storage temp.

2-8°C

Quality Level

200

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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.

General description

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

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

147.2 °F - closed cup

flash_point_c

64 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4521
BCCM1122
BCBR6377V
BCBK5885V
BCBB0790

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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
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:
Synlett, 65-65 (1993)
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