149437-76-3

Basic information

• Product Name: 4-(4-Fluorobenzoyl)butyric acid
• Synonyms: CHEMBRDG-BB 4002813;4-(4-FLUOROPHENYL)BUTYRIC ACID;4-(4-FLUOROBENZOYL)BUTYRIC ACID;4-(4-FLUOROBENZOYL)-1-BUTANOIC ACID;4-FLUORO-GAMMA-OXO-BENZENEPENTANOIC ACID;4-FLUOROPHENYL-5-OXOPENTANOIC ACID;4-FLUORO BENZOYL BUTYRIC ACID;5-(4'-FLUOROPHENYL)-5-OXOPENTANOIC ACID
• CAS NO: 149437-76-3
• Molecular Formula: C₁₁H₁₁FO₃
• Molecular Weight: 210.2
• EINECS: 1308068-626-2
• Product Categories: Acids & Esters;Fluorine Compounds;Intermediate of ezetimibe;Aromatics
• Mol File: 149437-76-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 142-144°C
• Boiling Point: 394.6 °C at 760 mmHg
• Flash Point: 192.5 °C
• Appearance: Off-white solid
• Density: 1.241 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol
• PKA: 4.59±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Fluorobenzoyl)butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Fluorobenzoyl)butyric acid(149437-76-3)
• EPA Substance Registry System: 4-(4-Fluorobenzoyl)butyric acid(149437-76-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• Hazardous Substances Data: 149437-76-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

4-Fluorophenyl-5’-oxobutyric Acid (cas# 149437-76-3) is a compound useful in organic synthesis.

Upstream product

• 108-55-4 glutaric anhydride, 
• 352-13-6 4-flourophenylmagnesium bromide 
• 462-06-6 fluorobenzene 
• 53715-97-2 5,5'-oxybis(5-oxopentanoic acid) 

Downstream Products

• 1187468-19-4 (3S,8aS)-8a-(4-fluoro-phenyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 852148-48-2 (4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one 
• 189028-93-1 (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 
• 1242183-65-8 3-(6-(4-fluorophenyl)-4-(furan-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid 
• 914777-32-5 6-(4-fluorophenyl)-3,4-dihydro-2H-pyran-2-one 
• 914777-33-6 1,9-bis(4-fluorophenyl)nonane-1,5,9-trione 
• 1258204-06-6 5-(4-fluorophenyl)pent-5-enoic acid 
• 1258203-99-4 (S)-6-(4-fluorophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one 
• 1261280-42-5 5-(4-fluorophenyl)hex-5-enoic acid methyl ester 
• 189028-95-3 (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one 
• 163222-33-1 ezetemibe 
• 1187468-22-9 (S)-2-(4-fluorophenyl)piperidine 
• 1187468-21-8 (R)-2-(4-fluorophenyl)piperidine 
• 163380-16-3 (3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one 

Relevant articles and documents

Chromatography-free stereoselective synthesis of (R)-3-benzylpiperidine

The present study describes aza-Michael addition reactions of 4-aroylpent-4-enoic acids with (R)-phenylglycinol. Subsequent spontaneous lactamization yielded the corresponding piperidin-2-ones, which can selectively crystallize in very high diastereomeric purity. These are useful intermediates in the stereoselective syntheses of diverse 3-benzylpiperidines, as herein demonstrated by a chromatography-free and straightforward Gram-scale synthesis of (R)-3-benzylpiperidine hydrochloride.

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Synthesis method of chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate

The invention provides a synthesis method of chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate. The method comprises the following steps: fluorobenzene and glutaric anhydride taken as raw materials undergo a Friedel-Crafts acylation reaction to synthesize 5-(4-fluorophenyl)-5-carbonylvaleric acid; the 5-(4-fluorophenyl)-5-carbonylvaleric acid undergoes a reduction reaction to synthesize 5-(4-fluorophenyl)-5-hydroxyvaleric acid; the 5-(4-fluorophenyl)-5-hydroxyvaleric acid undergoes a cyclization reaction to produce 6-(4-fluorophenyl)-tetrahydropyran-2-one; and the 6-(4-fluorophenyl)-tetrahydropyran-2-one undergoes an alcoholysis reaction to obtain the target compound, namely chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate. The synthesis method avoids the problem that carbonyl and ester groups are easy to reduce at the same time, has the advantages of solution control of reaction conditions, high yield, mild reaction temperature, simplicity, easiness in implementation and low cost,and can realize industrial production.