3-FLUORO-4-HYDROXYPHENYLACETIC ACID Chemical Properties

Melting point:

132-134 °C (lit.)

Boiling point:

320.3±27.0 °C(Predicted)

Density 

1.423±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.30±0.10(Predicted)

form 

Crystalline Powder

color 

White to beige

CAS DataBase Reference

458-09-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29182900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-FLUORO-4-HYDROXYPHENYLACETIC ACID Usage And Synthesis

Chemical Properties

White to beige crystalline powder

Synthesis

General procedure for the synthesis of 3-fluoro-4-hydroxyphenylacetic acid from 3-fluoro-4-methoxyphenylacetic acid: Aluminum chloride (42.8 g, 0.32 mol) was slowly added to 500 mL of toluene solution containing 3-fluoro-4-methoxyphenylacetic acid (45 g, 0.245 mol), and the temperature of the reaction was controlled to be no more than 25 °C. Subsequently, the reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, 260 mL of 10% hydrochloric acid was added to the cooled solution. The precipitate was collected by filtration and the filtrate was extracted twice with 75 mL of 1,2-dichloroethane. The organic extracts were combined and washed sequentially with 5% sodium hydroxide solution and water. The alkaline washings were combined with the previously collected precipitate and filtered through activated carbon after adjusting the pH to 12 with 5% sodium hydroxide solution. The filtrate was acidified with 50% sulfuric acid and the resulting oil was extracted with ether. The organic phase was dried and the solvent was evaporated to give 3-fluoro-4-hydroxyphenylacetic acid in a yield of 25 g (62% yield). The melting point of the product was 109-111 °C. Mass spectrum (ESI) m/z (relative abundance): 193.0 [M + Na]+.

Purification Methods

Crystallise the acid from water. [Beilstein 10 III 440.]

References

[1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 1, p. 296 - 306
[2] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 508 - 518
[3] Chemische Berichte, 1952, vol. 85, p. 577,580
[4] DRP/DRBP Org.Chem.,

3-FLUORO-4-HYDROXYPHENYLACETIC ACID(458-09-3)Related Product Information

• 3'-Fluoro-4'-hydroxyacetophenone
• 3-FLUORO-4-(TRIFLUOROMETHOXY)PHENYLACETIC ACID
• 2,3-DIFLUORO-4-METHOXYPHENYLACETIC ACID
• 3,5-DIFLUORO-4-METHOXYPHENYLACETIC ACID
• 3-FLUORO-4-HYDROXYPHENYLACETIC ACID
• 3-FLUORO-4-METHOXYPHENYLACETIC ACID
• 4-fluoro-à-hydroxyphenylacetic acid
• 2-Fluoro-4-hydroxyphenylacetic acid
• ETHYL 3-FLUORO-4-METHOXYBENZOYLFORMATE
• AMINO-(3-FLUORO-4-METHOXY-PHENYL)-ACETIC ACID
• Ethyl Difluoro-(3-fluoro-4-methoxyphenyl)acetate
• 2-Fluoro-5-hydroxyphenylacetic acid
• 4-Fluoro-3-hydroxyphenylacetic acid
• (2S)-2-AMINO-2-[3-FLUORO-4-(PHENYLMETHOXY)PHENYL]PROPANOIC ACID
• [3-(chlorosulfonyl)-5-fluoro-4-methoxyphenyl]acetic acid
• (2S)-2-AMINO-2-(3,5-DIFLUORO-4-METHOXYPHENYL)PROPANOIC ACID
• (2S)-2-AMINO-2-(3-FLUORO-4-[(4-NITROPHENYL)METHOXY]PHENYL)PROPANOIC ACID
• (2R)-2-AMINO-2-(3,5-DIFLUORO-4-METHOXYPHENYL)PROPANOIC ACID