| Identification | Back Directory | [Name]
4-(3,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER | [CAS]
374679-63-7 | [Synonyms]
AKOS B016273
ART-CHEM-BB B016273
SALOR-INT L100021-1EA
Methyl 3,4-dichloro-a,g-dioxo-benzenebutanoate
METHYL 4-(3,4-DICHLOROPHENYL)-2,4-DIOXOBUTANOATE
4-(3,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER
Benzenebutanoic acid, 3,4-dichloro-α,γ-dioxo-, methyl ester | [Molecular Formula]
C11H8Cl2O4 | [MDL Number]
MFCD03001261 | [MOL File]
374679-63-7.mol | [Molecular Weight]
275.08 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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