4-BROMO-2,6-DIFLUOROBENZYL ALCOHOL Chemical Properties

Melting point:

76-81 °C (lit.)

Boiling point:

250℃

Density 

1.744

Flash point:

105℃

storage temp. 

Sealed in dry,Room Temperature

form 

Solid

pka

13.21±0.10(Predicted)

color 

White to Light yellow

InChIKey

LSRHFWSNUFIKER-UHFFFAOYSA-N

CAS DataBase Reference

162744-59-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2906290090

MSDS

• Language:English Provider:SigmaAldrich

4-BROMO-2,6-DIFLUOROBENZYL ALCOHOL Usage And Synthesis

Uses

4-Bromo-2,6-difluorobenzyl alcohol is an organic intermediate. It has been reported that 4-bromo-2,6-difluorobenzyl alcohol can be used to prepare RET inhibitors.

Application

4-Bromo-2,6-difluorobenzyl alcohol can be used to prepare RET inhibitors.

Preparation

4-Bromo-2,6-difluorobenzyl alcohol can be obtained by reducing the carboxyl group from 4-bromo-3,5-difluorobenzoic acid.

Synthesis

General procedure for the synthesis of 4-bromo-2,6-difluorobenzenemethanol from 2,6-difluoro-4-bromobenzoic acid: to a solution of 2,6-difluoro-4-bromobenzoic acid (5 g, 21.10 mmol) in tetrahydrofuran (THF, 100 mL) was slowly added borane (BH3). Dimethyl sulfide (DMS, 20.03 mL, 211 mmol) was added dropwise at room temperature. The reaction mixture was stirred at 60 °C for 16 hours. After confirming complete consumption of the feedstock by liquid chromatography-mass spectrometry (LCMS) analysis, the reaction was quenched with methanol (MeOH). The solvent was evaporated under reduced pressure to afford 4-bromo-2,6-difluorobenzenemethanol as a white solid (4.5 g, 20.02 mmol, 95.2% yield), which could be used in subsequent reactions without further purification. Electrospray liquid chromatography-mass spectrometry (ES-LCMS) analysis showed m/z 222.1 ([M+H]+).

References

[1] Patent: US2014/275111, 2014, A1. Location in patent: Paragraph 0371; 0372
[2] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 81; 82
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 10, p. 3258 - 3262

4-BROMO-2,6-DIFLUOROBENZYL ALCOHOL(162744-59-4)Related Product Information

• 2-Bromoethanol
• 4-Bromo-2,6-difluorobenzoic acid
• 4-BROMO-2,3,5,6-TETRAFLUOROBENZOIC ACID
• Methyl 4-bromo-2,6-difluorobenzoate
• 4-BROMO-2,6-DIFLUOROBENZYL ALCOHOL
• 4-BROMO-2,3,5,6-TETRAFLUOROBENZYLALCOHOL
• 2,6-Difluorobenzyl alcohol
• RARECHEM AL BP 1306
• 4-BROMO-2,3,6-TRIFLUOROBENZYL ALCOHOL
• TERT-BUTYL 4-BROMO-2,6-DIFLUOROBENZOATE
• 6-BROMO-2,3-DIFLUOROBENZYL ALCOHOL
• ethyl 4-bromo-2,3,5,6-tetrafluorobenzimidate
• TERT-BUTYL 4-BROMO-2,3,5,6-TETRAFLUOROBENZOATE
• RARECHEM AL BE 1308
• RARECHEM AL BI 1306
• RARECHEM AL BF 1308
• RARECHEM AL BP 1308
• RARECHEM AL BI 1308