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| | 3-(4-FLUOROBENZOYL)PROPIONIC ACID Basic information |
| | 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 | | InChI | 1S/C10H9FO3/c11-8-3-1-7(2-4-8)9(12)5-6-10(13)14/h1-4H,5-6H2,(H,13,14) | | InChIKey | WUYWHIAAQYQKPP-UHFFFAOYSA-N | | SMILES | OC(=O)CCC(=O)c1ccc(F)cc1 | | CAS DataBase Reference | 366-77-8(CAS DataBase Reference) |
| 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 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | 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 Preparation Products And Raw materials |
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