METHYL 4-FLUORO-2-HYDROXYBENZOATE Chemical Properties

Melting point:

38-40°C

Boiling point:

225℃

Density 

1.309

Flash point:

90℃

storage temp. 

Sealed in dry,Room Temperature

form 

crystalline solid

pka

8.76±0.10(Predicted)

color 

Off white to light yellow/brown

BRN 

2087920

CAS DataBase Reference

392-04-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard Note 

Irritant

HS Code 

2916310090

MSDS

• Language:English Provider:ALFA

METHYL 4-FLUORO-2-HYDROXYBENZOATE Usage And Synthesis

Uses

Methyl 4-Fluoro-2-hydroxybenzoate is a useful synthetic intermediate. It was used to prepare benzo[d]isoxazol-3-ol as D-amino acid oxidase inhibitors. It is also used in the discovery of hydroxy-indazole-carboxamides as inhibitors of Hsp90.

Synthesis

To a solution of 100 g (0.64 mol, 1.0 eq.) of 4-fluoro-2-hydroxybenzoic acid (XLIa) dissolved in 1 L of methanol at 0 °C was slowly added 100 mL of concentrated sulfuric acid. The reaction mixture was gradually warmed to room temperature and subsequently heated to reflux at 70 °C for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove most of the methanol. The concentrated residue was redissolved in 1 L of ethyl acetate and washed sequentially with 500 mL of saturated aqueous sodium bicarbonate and 500 mL of saturated saline. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford 95 g (0.56 mol, 87% yield) of methyl 4-fluoro-2-hydroxybenzoate (XLIIa).

References

[1] Chemical and Pharmaceutical Bulletin, 2012, vol. 60, # 2, p. 223 - 234
[2] Patent: WO2018/148204, 2018, A1. Location in patent: Page/Page column 176
[3] Patent: WO2018/172852, 2018, A1. Location in patent: Page/Page column 214; 222-223
[4] Patent: CN107501260, 2017, A. Location in patent: Paragraph 0030; 0031; 0032; 0035; 0036
[5] Acta Chemica Scandinavica, 1997, vol. 51, # 8, p. 881 - 888

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