3-(2-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

3-(2-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER Property

Boiling point:

221-222 °C (lit.)

Density 

1.206 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.540(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

pka

9.85±0.46(Predicted)

Appearance

Colorless to light yellow Liquid

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

3-(2-CHLORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER Chemical Properties,Usage,Production

Uses

Reactant for:

• Cerium ammonium nitrate-mediated oxidative coupling
• Hydrosilylation reactions
• Preparation of diaryl-substituted pyrazoles as potent CCR2 receptor antagonists
• Preparation of potential herbicidal agents
• Ruthenium-catalyzed asymmetric hydrogenation

Synthesis

GENERAL STEPS: EXPERIMENTAL OPERATION: Potassium monoethyl malonate salt (1.00 g, ~5.47 mmol) was taken in a 25 mL round bottom flask, anhydrous magnesium chloride (0.65 g, ~6.84 mmol) and acetonitrile (6 mL) were added, followed by the dropwise addition of triethylamine (0.55 g). The mixture was stirred at room temperature for 30 minutes. Next, a solution of o-chlorobenzoyl chloride (0.48 g, 2.5 mmol) dissolved in acetonitrile (2 mL) was slowly added dropwise and supplemented with triethylamine (0.06 mL), and stirring was continued at room temperature overnight. Post-treatment: after completion of the reaction, the reaction mixture was diluted with the addition of water (30 mL) and subsequently extracted with ethyl acetate (30 mL, 20 mL, 20 mL). The ethyl acetate layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The dried organic phase was concentrated by rotary evaporation and finally purified by column chromatography (eluent: petroleum ether/ethyl acetate=15:1) to afford the target product (2-chlorobenzoyl)ethyl acetate in 91% yield.

References

[1] Patent: CN105566340, 2016, A. Location in patent: Paragraph 0010
[2] Patent: CN105663112, 2016, A. Location in patent: Page/Page column 12