| Identification | More | [Name]
3-(4-FLUOROBENZOYL)PROPIONIC ACID | [CAS]
366-77-8 | [Synonyms]
3-(4'-FLUOROBENZOYL)PROPIONIC ACID
3-(4-FLUOROBENZOYL)PROPIONIC ACID
4-(4-FLUOROPHENYL)-4-OXOBUTANOIC ACID
4-(4-FLUOROPHENYL)-4-OXOBUTYRIC ACID
AKOS BBS-00006441
HALOPERIDOL METABOLITE III
LABOTEST-BB LT00233221
R 11302
4-FLUORO-R-OXO-BENZENEBUTANOIC ACID
Benzenebutanoic acid, 4-fluoro-.gamma.-oxo-
3-(4-Fluorobenzoyl)propionic acid 97%
3-(4-Fluorobenzoyl)propionicacid97%
beta-(4-fluorobenzoyl)propionic acid
4-Fluoro-oxo-benzenebutanoic acid
Haloperidol metabolite III, R 11302
4-Fluoro-γ-oxobenzenebutyric acid
4-Oxo-4-(4-fluorophenyl)butyric acid
β-(p-Fluorobenzoyl)propionic acid | [EINECS(EC#)]
206-679-1 | [Molecular Formula]
C10H9FO3 | [MDL Number]
MFCD00002793 | [Molecular Weight]
196.18 | [MOL File]
366-77-8.mol |
| Chemical Properties | Back Directory | [Appearance]
beige granular powder | [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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H335-H315-H319-H302 | [Precautionary statements ]
P280g-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | [Hazard Codes ]
Xn,C,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Corrosive | [HazardClass ]
IRRITANT | [HS Code ]
29183000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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 |
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