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Ethyl malonyl chloride, 95%

Name: Ethyl malonyl chloride, 95%
SKU: A15616.22
Price: 686.65 USD

CAS: 36239-09-5 | C5H7ClO3 | 150.56 g/mol

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Catalog number A15616.22

also known as A15616-22

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686.65

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Quantity:

100 g

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Price (USD)

686.65

Online Exclusive

763.00

Save 76.35 (10%)

Each

Chemical Identifiers

CAS36239-09-5

IUPAC Nameethyl 3-chloro-3-oxopropanoate

Molecular FormulaC5H7ClO3

InChI KeyKWFADUNOPOSMIJ-UHFFFAOYSA-N

SMILESCCOC(=O)CC(Cl)=O

Specifications

Specification Sheet

Assay (Titration ex Chloride)≥94.0 to ≤106.0%

FormLiquid

Appearance (Color)Clear colorless to yellow

Refractive Index1.4265-1.4325 @ 20?C

Ethyl malonyl chloride is used in the syntheses of methanofullerodendimers and 3-pyrrolin-2-ones. It plays a vital role in the preparation of 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks. It is a versatile acylating agent for propargyl alcohols, hydrazines and amines.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Ethyl malonyl chloride is used in the syntheses of methanofullerodendimers and 3-pyrrolin-2-ones. It plays a vital role in the preparation of 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks. It is a versatile acylating agent for propargyl alcohols, hydrazines and amines.

Solubility
Miscible with water.

Notes
Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with alcohols. It reacts with water.

RUO – Research Use Only

General References:

Useful synthetic building block, e.g. in an oxazole synthesis: J. Med. Chem., 36, 3871 (1993):
Formation of amides has been used in the syntheses of 1,2,4-triazine-3,6-diones, and of a vicinal tricarbonyl amide derivative of L-phenylalanine: J. Org. Chem., 60, 5992 (1995); 61, 1872 (1996).
Yang, Z.; Li, S.; Zhang, Z.; Xu, J. Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines. Org. Biomol. Chem. 2014, 12 (48), 9822-9830.
Hayat, F.; Kang, L.; Lee, C. Y.; Shin, D. Synthesis of arylnaphthalene lignan lactone using benzoin condensation, intramolecular thermal cyclization and Suzuki coupling. Tetrahedron 2015, 71 (19), 2945-2950.