| Identification | Back Directory | [Name]
2-BROMO-5-CHLOROBENZYL ALCOHOL | [CAS]
60666-70-8 | [Synonyms]
2-Bromo-5-chlorobenzyl alcoho
2-BROMO-5-CHLOROBENZYL ALCOHOL
2-bromo-5-chloroBenzenemethanol
(2-Bromo-5-chlorophenyl)methanol
Benzenemethanol, 2-bromo-5-chloro- | [Molecular Formula]
C7H6BrClO | [MDL Number]
MFCD09261147 | [MOL File]
60666-70-8.mol | [Molecular Weight]
221.48 |
| Chemical Properties | Back Directory | [Melting point ]
81-83°C | [Boiling point ]
290℃ | [density ]
1.685 | [Fp ]
129℃ | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
solid | [pka]
13.67±0.10(Predicted) |
| Hazard Information | Back Directory | [Uses]
2-Bromo-5-chlorobenzyl Alcohol is used to prepare fluorodihydrohydroxy benzoxaborole for potential treatment of onychomycosis. It is also an intermediate used to synthesize morpholylureas as potent and selective inhibitors of AKR1C3. | [Synthesis]
Under nitrogen protection, 2-bromo-5-chlorobenzoic acid (17-1, 5.0 g, 21.23 mmol) was dissolved in BH3/THF solution (1 M, 85 mL) at a controlled temperature of 10 °C. After the addition was completed, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, methanol (30 mL) was added slowly at 0 °C to quench the reaction, after which the mixture was concentrated to dryness. The resulting residue was dissolved in methanol (100 mL) and concentrated again to dryness. This dissolution-concentration procedure was repeated twice to give 2-bromo-5-chlorobenzenemethanol (17-2) as a white solid (4.7 g, quantitative yield). | [References]
[1] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 295
[2] Patent: WO2012/131588, 2012, A1. Location in patent: Page/Page column 96; 108
[3] Chemical Communications, 2018, vol. 54, # 20, p. 2467 - 2470
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450
[5] Patent: US2007/265226, 2007, A1. Location in patent: Page/Page column 58 |
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