4-(3,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER

4-(3,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER Property

Melting point:

127-129°C

Boiling point:

423.0±40.0 °C(Predicted)

Density 

1.410±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

5.72±0.48(Predicted)

Appearance

Off-white to light yellow Solid

Safety

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye 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.

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

P337+P313IF eye irritation persists: Get medical advice/attention.

4-(3,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of methyl 4-(3,4-dichlorophenyl)-2,4-dicarbonylbutyrate from dimethyl oxalate and 3,4-dichloroacetophenone: dimethyl oxalate (5.9 g, 50 mmol) was slowly added to a suspension of freshly prepared sodium methanolate (3.24 g, 60 mmol) in anhydrous toluene at 8-10 °C. Subsequently, 3,4-dichloroacetophenone (6.7 g, 50 mmol) was added dropwise over 30 min. The reaction mixture was stirred overnight at 8-10 °C and under nitrogen protection. After completion of the reaction, the yellow precipitate was obtained by filtration and washed with toluene (2 x 20 ml), then the precipitate was dissolved in water (20 mL) and acidified by adding 25 ml of 6N HCl. The organic layer was extracted with diisopropyl ether, followed by washing the organic layer with brine, drying with anhydrous sodium sulfate, and finally evaporating the solvent to give pure methyl 4-(3,4-dichlorophenyl)-2,4-dicarbonylbutyrate (8a-e) as a yellow solid in good yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 2077 - 2083
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 273 - 280