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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/REAXYS Number:
636215
EC Number:
252-934-5
MDL number:
MFCD00000736
UNSPSC Code:
12352100
PubChem Substance ID:
24850040
NACRES:
NA.22
Pricing and availability is not currently available.

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.)

functional group

acyl chloride
ester

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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1 of 4

This Item
W478601W403622W236608
2-Octyl-2-dodecenal mixture of cis and trans, 94%

W478515

2-Octyl-2-dodecenal

2-Hexyl-2-decenal mixture of cis and trans, ≥95%

W478601

2-Hexyl-2-decenal

cis-4-Dodecenal ≥94%, stabilized, FG

W403622

cis-4-Dodecenal

trans-2-Decenal ≥95%, FCC, FG

W236608

trans-2-Decenal

grade

Halal, Kosher

grade

Halal, Kosher

grade

FG, Halal, Kosher

grade

FG, Halal, Kosher

biological source

synthetic

biological source

synthetic

biological source

synthetic

biological source

synthetic

food allergen

no known allergens

food allergen

no known allergens

food allergen

no known allergens

food allergen

no known allergens

assay

94%

assay

≥95%

assay

≥94%

assay

≥95%

documentation

see Safety & Documentation for available documents

documentation

see Safety & Documentation for available documents

documentation

see Safety & Documentation for available documents

documentation

see Safety & Documentation for available documents

General description

Ethyl malonyl chloride is a versatile acylating agent for propargyl alcohols[1], hydrazines[2] and amines[3].

Application

Ethyl malonyl chloride was used in the synthesis of:
  • liquid-crystalline methanofullerodendrimers[4]
  • 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks[5]
  • 3-pyrrolin-2-ones via amidation with propargylamines and subsequent base catalyzed 5-exo-dig cyclization[6]
Versatile acylating agent for propargyl alcohols,[1] hydrazines,[2] and amines.[3]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

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
BCBR6377V
BCBK5885V
BCBB0790
BCBF4412V
BCBB0790V

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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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