589-06-0

Basic information

• Product Name: 4-(4-Fluorophenyl)butanoic acid
• Synonyms: TIMTEC-BB SBB010216;CHEMBRDG-BB 4002813;4-(4-FLUOROPHENYL)BUTYRIC ACID;4-(p-fluorophenyl)butyric acid;4-(4-Fluorophenyl)butanoic acid;4-Fluorobenzenebutanoic acid;Benzenebutanoic acid, 4-fluoro-
• CAS NO: 589-06-0
• Molecular Formula: C₁₀H₁₁FO₂
• Molecular Weight: 182.19
• EINECS: 209-631-8
• Product Categories: Aliphatics;Carboxylic Acids;Carboxylic Acids;Aromatic Building Blocks
• Mol File: 589-06-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 296.5°C at 760mmHg
• Flash Point: 133.1°C
• Appearance: /
• Density: 1.182g/cm³
• Vapor Pressure: 0.000646mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Fluorophenyl)butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Fluorophenyl)butanoic acid(589-06-0)
• EPA Substance Registry System: 4-(4-Fluorophenyl)butanoic acid(589-06-0)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 589-06-0(Hazardous Substances Data)

Usage

General Description

4-(4-Fluorophenyl)butanoic acid, also known as 4-fluoro-α-methylphenylbutyric acid, is a chemical compound with the molecular formula C10H11FO2. It is a derivative of butanoic acid and contains a fluorine-substituted phenyl group. This chemical is typically used in the pharmaceutical industry as an intermediate for the synthesis of various compounds, including medications and research chemicals. It has properties that make it useful for developing new drugs and studying their effects on the body. 4-(4-Fluorophenyl)butanoic acid is also known to have some potential as an antidepressant and anticonvulsant, making it an important compound for research and development in the medical field.

InChI:InChI=1/C10H11FO2/c11-9-6-4-8(5-7-9)2-1-3-10(12)13/h4-7H,1-3H2,(H,12,13)/p-1

Upstream product

• 366-77-8 4-(4-fluorophenyl)-4-oxopropionic acid 
• 3200-99-5 4-[4-(4-fluoro-phenyl)-butyryl]-thiomorpholine 
• 1117-71-1 methyl 4-bromocrotonate 
• 17151-47-2 tributyl(4-fluorophenyl)stannane 
• 127404-66-4 4-(4-fluorophenyl)but-3-enoic acid 
• 462-06-6 fluorobenzene 
• 582-83-2 1-(4-fluorophenyl)butan-1-one 
• 459-57-4 4-fluorobenzaldehyde 
• 51787-96-3 5-(4-fluorophenyl)dihydrofuran-2(3H)-one 
• 625-38-7 but-3-enoic acid 
• 1765-93-1 4-fluoroboronic acid 

Downstream Products

• 20637-05-2 methyl 4-(4-fluorophenyl)butanoate 
• 2840-44-0 7-fluoro-3,4-dihydronaphthalen-1(2H)-one 
• 1693-05-6 ethyl 4-(4'-fluorophenyl)butanoate 
• 133188-66-6 4-(4-fluorophenyl)butyryl chloride 
• 40283-05-4 4-(4-fluorophenyl)-1-butanol 
• 51787-96-3 5-(4-fluorophenyl)dihydrofuran-2(3H)-one 
• 89326-70-5 1-bromo-4-(4-fluorophenyl)-butane 
• 149080-28-4 4-p-fluorophenylbutylamine 
• 220728-25-6 2-[4-(4-fluorophenyl)butyl]isoindoline-1,3-dione 
• 89326-72-7 6-(4'-fluorophenyl)hexanoic acid 
• 89326-76-1 6-(4-Fluoro-phenyl)-hexanoyl chloride 
• 89326-71-6 ethyl 2-ethoxycarbonyl-6-(4'-fluorophenyl)hexanoate 
• 89347-14-8 6-(4-Fluoro-phenyl)-hexanoic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 2840-40-6 6-Fluoro-1,2,3,4-tetrahydro-2-naphthalene 

Relevant articles and documents

Practical Synthesis of (3a R, 9b R)-8-Fluoro-7-(perfluoropropan-2-yl)-9b-(phenylsulfonyl)-2,3,3a,4,5,9b-hexahydro-1 H-benzo[e]indole: An Advanced Intermediate to Access the RORγt Inverse Agonist BMT-362265

A practical and scalable route to (3aR, 9bR)-8-fluoro-7-(perfluoropropan-2-yl)-9b-(phenylsulfonyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole 10, an advanced intermediate en route to the synthesis of the RORγt inverse agonist, BMT-362265, is described starting from fluorobenzene. The synthesis involved the screening of multiple synthetic routes for their feasibility and scalability. We also demonstrate the utility of an annulating reagent, (R)-N-(2-chloroethyl)-2-methylpropane-2-sulfinamide, for the diastereoselective synthesis of tricyclic pyrrolidine intermediates 24 and 36 on a multigram scale.

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**

A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.