Identification | Back Directory | [Name]
Methyl-4,5-dibromo-2-furoate | [CAS]
54113-41-6 | [Synonyms]
Methyl-4,5-dibromo-2-furoate methyl 4,5-dibromofuran-2-carboxylate Methyl 4,5-Dibromo-2-furancarboxylate 4,5-Dibromo-2-furoic Acid Methyl Ester 4,5-Dibromofuran-2-carboxylicacid methyl ester 4,5-Dibromo-2-furancarboxylic Acid Methyl Ester 2-Furancarboxylic acid, 4,5-dibromo-, methyl ester | [Molecular Formula]
C6H4Br2O3 | [MDL Number]
MFCD00092493 | [MOL File]
54113-41-6.mol | [Molecular Weight]
283.902 |
Chemical Properties | Back Directory | [Melting point ]
56.0 to 60.0 °C | [Boiling point ]
110°C/0.8mmHg(lit.) | [density ]
1.992±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform, Dichloromethane, Ethyl Acetate, Methanol | [form ]
Solid | [color ]
Off White |
Hazard Information | Back Directory | [Uses]
Methyl 4,5-dibromo-2-furoate is an intermediate in the synthesis of 4-Amino-2-furancarboxylic Acid (A609680), which is the characteristic structural element of the Proximicins. Proximicin A, B and C, are novel aminofuran antibiotic and anticancer compounds isolated from marine strains of the actinomycete Verrucosispora. | [Synthesis]
Preparative Example 2-1 Synthesis of methyl 4,5-dibromofuran-2-carboxylate Procedure: a catalytic amount of oxalyl chloride (210 μL, 2.4 mmol) was added slowly and dropwise to a mixed solution of dichloromethane (5.0 mL) and N,N-dimethylformamide containing 4,5-dibromofuran-2-carboxylic acid (500 mg, 1.9 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the solvent was removed by distillation under reduced pressure, triethylamine (340 μL, 2.4 mmol) and methanol (4.0 mL) were added, and stirring was continued for 1 h at room temperature. Upon completion of the reaction, the solvent was again removed by distillation under reduced pressure, saturated aqueous sodium bicarbonate was added, and extraction was carried out with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried with anhydrous sodium sulfate. Finally, the solvent was removed by reduced pressure distillation to afford the target product methyl 4,5-dibromofuran-2-carboxylate (460 mg, 88% yield). The product was characterized by 1H-NMR (400 MHz, CDCl3) with chemical shifts δ (ppm) of 3.90 (s, 3H), 7.18 (s, 1H). | [References]
[1] Patent: US2006/160874, 2006, A1. Location in patent: Page/Page column 21 [2] Patent: WO2004/7504, 2004, A1. Location in patent: Page 54-55 [3] Patent: WO2008/98104, 2008, A1. Location in patent: Page/Page column 216-217 [4] Patent: US2016/168176, 2016, A1. Location in patent: Paragraph 0241; 0242 |
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TCI Europe
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TCI AMERICA
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SynAsst Chemical.
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