Ethyl malonyl chloride Chemical Properties

Boiling point:

79-80 °C25 mm Hg(lit.)

Density 

1.196 g/mL at 20 °C

refractive index 

n20/D 1.429(lit.)

Flash point:

154 °F

storage temp. 

2-8°C

solubility 

Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly)

form 

Liquid

pka

9.35±0.46(Predicted)

Specific Gravity

1.176

color 

Clear yellow to brown

Water Solubility 

REACTS

Sensitive 

Moisture Sensitive

BRN 

636215

Stability:

Hygroscopic, Moisture Sensitive

InChI

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

InChIKey

KWFADUNOPOSMIJ-UHFFFAOYSA-N

SMILES

CCOC(=O)CC(Cl)=O

CAS DataBase Reference

36239-09-5(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl malonyl chloride(36239-09-5)

Safety Information

Hazard Codes 

C

Risk Statements 

14-34

Safety Statements 

7-26-36/37/39-45-36/39

RIDADR 

UN 3265 8/PG 3

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29171900

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Skin Corr. 1B

MSDS

• Language:English Provider:Ethyl (chloroformyl)acetate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl malonyl chloride Usage And Synthesis

Chemical Properties

clear yellow to brown liquid

Uses

Employed in the synthesis of 3-pyrrolin-2-ones via amidation with propargylamines and subsequent base catalyzed 5-exo-dig cyclization.1

Uses

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.

General Description

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

Synthesis

Method I. Ethyl chloroformylacetate, also known as ethyl 3-chloro-3-oxopropionate, ethyl malonate monochloride, can be obtained by chlorination of 3-ethoxy-3-oxopropionic acid, and the chlorination reagent can be selected from sulfoxide chloride and oxalyl chloride.
To a solution of toluene (226 mL) containing 3-ethoxy-3-oxopropionic acid (14.9 g, 112.8 mmol) was added dichlorosulfoxide (26.6 g, 225.6 mmol). The reaction solution was heated and stirred at 110??C for 4 hours and then concentrated under reduced pressure to give ethyl chloroformylacetate as a brown oil.
Method II, ethyl malonate (13.2g,100.0mmol) and N,N-dimethylformamide (0.05mL) were stirred and dissolved in dichloromethane (200mL), cooled to 0??C in an ice-water bath, oxalic acid chloride (25.4g,200mmol) was added dropwise, and the mixture was stirred at room temperature for 2h, and concentrated to obtain ethyl chloroformyl acetate (14.5g,97%) as a white oily material.

Ethyl malonyl chloride(36239-09-5)Related Product Information

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