| Identification | Back Directory | [Name]
(4-BROMO-3-FLUOROPHENYL)METHANOL | [CAS]
222978-01-0 | [Synonyms]
4-Bromo-3-fluorobenzenemethanol
(4-BROMO-3-FLUOROPHENYL)METHANOL
4-Bromo-3-fluorobenzylalcohol,96%
BenzeneMethanol, 4-broMo-3-fluoro-
(4-BROMO-3-FLUOROPHENYL)METHANOL ISO 9001：2015 REACH | [Molecular Formula]
C7H6BrFO | [MDL Number]
MFCD08236860 | [MOL File]
222978-01-0.mol | [Molecular Weight]
205.02 |
| Chemical Properties | Back Directory | [Melting point ]
44.0 to 48.0 °C | [Boiling point ]
260℃ | [density ]
1.658 | [Fp ]
111℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
13.70±0.10(Predicted) | [color ]
White to Almost white |
| Hazard Information | Back Directory | [Uses]
(4-Bromo-3-fluorophenyl)methanol is used to prepare triazolopyridyl compounds, which can be used as a prodrug of RIPK1 inhibitors. | [Synthesis]
GENERAL METHODS: Borane-tetrahydrofuran complex (BH3-THF, 89 mL, 89.49 mmol) was slowly added dropwise to a stirred solution of 3-fluoro-4-bromobenzoic acid (9.8 g, 44.75 mmol) in tetrahydrofuran (THF, 200 mL) at 25 °C. The dropwise addition was controlled to be completed in 10 min, and the reaction was carried out under nitrogen protection. The reaction mixture was stirred continuously at room temperature for 2 days. Upon completion of the reaction, the reaction was carefully quenched with 2 M sodium carbonate solution (Na2CO3, 200 mL) and subsequently extracted with ether (Et2O, 2 x 500 mL). The organic phases were combined, washed with saturated brine (400 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give a pale yellow oil. The crude product was purified by fast silica gel column chromatography, the eluent was a mixture of heptane and ethyl acetate (EtOAc) with a gradient elution ratio of 0 to 70% ethyl acetate. The purified fraction was collected and concentrated to dryness under reduced pressure to give 4-bromo-3-fluorobenzyl alcohol (8.65 g, 94% yield) as a white solid. | [References]
[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 21, p. 9096 - 9104
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[3] Synlett, 2014, vol. 25, # 1, p. 123 - 127
[4] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 506 - 524
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260 |
|
|