| Identification | More | [Name]
5-Bromo-2,3-dihydro-1-benzofuran | [CAS]
66826-78-6 | [Synonyms]
5-BROMO-2,3-DIHYDRO-1-BENZOFURAN
5-BROMO-2,3-DIHYDROBENZO[B]FURAN
5-BROMO-2,3-DIHYDROBENZOFURAN
BUTTPARK 36\18-16 | [Molecular Formula]
C8H7BrO | [MDL Number]
MFCD02677716 | [Molecular Weight]
199.04 | [MOL File]
66826-78-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
49 °C | [Boiling point ]
251.7±29.0 °C(Predicted) | [density ]
1.582±0.06 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [color ]
White to Light yellow | [CAS DataBase Reference]
66826-78-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [HS Code ]
2932990090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
5-Bromo-2,3-dihydrobenzofuran, is an organic building block that can be used in the synthesis of Darifenacin (D193400), a drug used to treat urinary incontinence. | [Synthesis]
General procedure for the synthesis of 5-bromo-2,3-dihydrobenzofuran from 2,3-dihydrobenzofuran: Liquid bromine (2.66 g) was added slowly and dropwise to dioxane (30 mL) under cooling conditions in an ice bath and stirred for 30 min at this temperature. Subsequently, 2,3-dihydrobenzofuran (2 g) was added dropwise to the reaction mixture and stirring was continued for 3 hours at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (50 mL), washed sequentially with saturated aqueous sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to give an orange oily crude product. The crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 20:1) to afford 2.33 g of 5-bromo-2,3-dihydrobenzofuran white crystals in 70.3% yield. The product was characterized by 1H-NMR (300 MHz, CDCl3, δ): 3.11 (2H, t, J = 11 Hz), 4.57 (2H, t, J = 11 Hz), 6.66 (1H, d, J = 8 Hz), 7.20 (1H, d, J = 8 Hz), 7.30 (1H, s). | [References]
[1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4313 - 4336
[2] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047
[3] Synthesis, 1988, # 12, p. 950 - 952
[4] Patent: US6333324, 2001, B1
[5] Patent: WO2003/82787, 2003, A1. Location in patent: Page/Page column 137-138 |
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