(4-BROMO-3-FLUOROPHENYL)METHANOL Chemical Properties

Melting point:

44.0 to 48.0 °C

Boiling point:

260℃

Density 

1.658

Flash point:

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

Safety Information

HS Code 

2906290090

(4-BROMO-3-FLUOROPHENYL)METHANOL Usage And Synthesis

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

(4-BROMO-3-FLUOROPHENYL)METHANOL(222978-01-0)Related Product Information

• (4-BROMO-3-FLUOROPHENYL)METHANOL
• METHYL 4-BROMO-3-FLUOROBENZOATE 98
• 4-BROMO-2,3,5,6-TETRAFLUOROBENZYLALCOHOL
• 4-Bromo-3-fluorobenzoic acid
• 4-BROMO-2,3,5,6-TETRAFLUOROBENZOIC ACID
• 4-BROMO-3-FLUOROBENZOIC ACID ETHYL ESTER
• TERT-BUTYL 4-BROMO-3-FLUOROBENZOATE
• 4-BROMO-2-CHLORO-5-FLUOROBENZOIC ACID
• 2-AMINO-4-BROMO-5-FLUOROBENZOIC ACID
• 4-BROMO-5-FLUORO-2-NITROBENZOIC ACID
• 4-bromo-2,5-difluorobenzoic acid
• 4-BROMO-2,3-DIFLUOROBENZOIC ACID
• 4-BROMO-2,3,6-TRIFLUOROBENZYL ALCOHOL
• ethyl 4-bromo-2,3,5,6-tetrafluorobenzimidate
• RARECHEM AL BP 1308
• RARECHEM AL BI 1308
• TERT-BUTYL 4-BROMO-2,3,5,6-TETRAFLUOROBENZOATE
• RARECHEM AL BF 1308