3-(4-FLUOROBENZOYL)PROPIONIC ACID Chemical Properties

Melting point:

100-102 °C (lit.)

Boiling point:

374.4±22.0 °C(Predicted)

Density 

1.2441 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

4.50±0.17(Predicted)

color 

White to Orange to Green

Water Solubility 

Insoluble in water.

BRN 

958145

CAS DataBase Reference

366-77-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,C,Xi

Risk Statements 

36/37/38-20/21/22-22

Safety Statements 

36/37/39-26-22-24/25

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

IRRITANT

HS Code 

29183000

MSDS

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

3-(4-FLUOROBENZOYL)PROPIONIC ACID Usage And Synthesis

Chemical Properties

beige granular powder

Uses

7-Fluoro-1-tetralone was prepared from 3-(4-fluorobenzoyl)-propionic acid by Wolff-Kishner reduction followed by ring closure with polyphosphoric acid and other substituted 1-tetralones where commercially available. Reduction of 3-(4-fluorobenzoyl)propionic acid with an excess of tert-butylamine borane (TBAB) in the presence of AlCl3 provided 4-(4-fluorophenyl)-1-butanol (87) in 63% yield for the synthesis of LM-1507 sodium salt. Penfluridol 1-[4,4-bis(4-fluorophenyl)butyl]-4-(4-chloro-3-trifluoromethylphenyl)- 4-hydroxypiperidine, C 28 H 27 ClF 5 NO, M r 523.99, mp 105 - 107°C, is obtained by reducing the ketone of 3-(4-fluorobenzoyl)propionic acid into a lactone.

Definition

ChEBI: 4-(4-Fluorophenyl)-4-oxobutanoic acid is an aromatic ketone.

General Description

3-(4-Fluorobenzoyl)propionic acid is a metabolite of haloperidol, a dopamine D2 receptor blocker.

Synthesis

1. aluminum chloride (2.66 g, 20 mmol) was slowly added to a stirred mixture of succinic anhydride (1.00 g, 10 mmol) and fluorobenzene (5.6 mL, 60 mmol) at -5 °C. 2. the reaction temperature was maintained at -5 °C for 1 hour, followed by a slow warming to room temperature, and the reaction continued for 17 hours. 3. the reaction mixture was slowly poured into a stirred 18% HCl aqueous solution (30 mL) at 0 °C and stirring was continued for 30 min while the mixture was allowed to gradually warm up to room temperature. 4. The resulting white powder was collected by filtration and washed with deionized water. 5. The product was 4-(4-(4-hydroxyphenyl)ethyl)ethyl). 5. The product was 4-(4-fluorophenyl)-4-oxobutyric acid in 1.67 g, 85% yield. 6. ; HPLC tR = 1.53 min (>99% purity, mobile phase is an aqueous solution of 80% MeCN).

References

[1] Helvetica Chimica Acta, 1995, vol. 78, # 3, p. 647 - 662
[2] Patent: WO2007/96647, 2007, A2. Location in patent: Page/Page column 148-149
[3] Patent: CN107556287, 2018, A. Location in patent: Paragraph 0036; 0037; 0038; 0039; 0040; 0052; 0053
[4] Patent: CN106187863, 2016, A. Location in patent: Paragraph 0153; 0154; 0155; 0156; 0157; 0104-0108
[5] Tetrahedron Letters, 2016, vol. 57, # 24, p. 2583 - 2586

3-(4-FLUOROBENZOYL)PROPIONIC ACID(366-77-8)Related Product Information

• 3-(2',4'-DIFLUOROBENZOYL)PROPIONIC ACID
• METHYL 4-(4-FLUOROPHENYL)-2,4-DIOXOBUTANOATE
• 3-(4-FLUOROBENZOYL)PROPIONIC ACID
• Haloperidol
• ethyl 4-(2,4-difluorophenyl)-2,4-dioxobutanoate
• TRANS-2-(4-FLUOROBENZOYL)CYCLOPENTANE-1-CARBOXYLIC ACID
• 2-METHYL-4-OXO-4-(4'-FLUOROPHENYL)BUTYRIC ACID
• 4-(3,4-DIFLUOROPHENYL)-4-OXOBUTYRIC ACID
• TRANS-2-(4-FLUOROBENZOYL)-1-CYCLOHEXANE-CARBOXYLIC ACID, 99
• CIS-2-(4-FLUOROBENZOYL)-1-CYCLOHEXANE-CARBOXYLIC ACID, 99
• ETHYL 4-(3,4-DIFLUOROPHENYL)-2,2-DIMETHYL-4-OXOBUTYRATE
• ETHYL 4-(4-FLUOROPHENYL)-4-OXOBUTYRATE
• CIS-2-(4-FLUOROBENZOYL)CYCLOPENTANE-1-CARBOXYLIC ACID
• ETHYL 4-(3,4-DIFLUOROPHENYL)-4-OXOBUTYRATE
• 4-OXO-4-(3,4,5-TRIFLUOROPHENYL)BUTYRIC ACID
• ETHYL 4-(2,4-DIFLUOROPHENYL)-4-OXOBUTYRATE
• ETHYL 4-OXO-4-(3,4,5-TRIFLUOROPHENYL)BUTYRATE
• 4-(4-fluorophenyl)-4-oxo-2-[(2-thienylmethyl)amino]butanoic acid