3-(4-Fluorobenzoyl)propionic acid

Base Information

• Chemical Name: 3-(4-Fluorobenzoyl)propionic acid
• CAS No.: 366-77-8
• Molecular Formula: C10H9FO3
• Molecular Weight: 196.178
• Hs Code.: 29183000
• European Community (EC) Number: 206-679-1
• NSC Number: 408180
• UNII: V2Z6N6JC9Z
• DSSTox Substance ID: DTXSID30190084
• Nikkaji Number: J76.352G
• Wikidata: Q27291465
• ChEMBL ID: CHEMBL3544869
• Mol file: 366-77-8.mol

Synonyms:(18F)-beta-(4-fluorobenzoyl)propionic acid;4-FBPA;beta-(4-fluorobenzoyl)propionic acid

Chemical Property of 3-(4-Fluorobenzoyl)propionic acid

Chemical Property:

• Appearance/Colour: beige granular powder
• Vapor Pressure: 2.85E-06mmHg at 25°C
• Melting Point: 100-102 °C
• Refractive Index: 1.528
• Boiling Point: 374.4 °C at 760 mmHg
• PKA: 4.50±0.17(Predicted)
• Flash Point: 180.3 °C
• PSA: 54.37000
• Density: 1.284 g/cm³
• LogP: 1.87320
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 196.05357231
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

4-(4-Fluorophenyl)-4-oxobutanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, C, Xi
• Hazard Codes: Xn,C,Xi
• Statements: 36/37/38-20/21/22-22
• Safety Statements: 36/37/39-26-22-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)CCC(=O)O)F
• 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.

Technology Process of 3-(4-Fluorobenzoyl)propionic acid

There total 9 articles about 3-(4-Fluorobenzoyl)propionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

succinic acid anhydride (108-30-5) + fluorobenzene (462-06-6) → 4-(4-fluorophenyl)-4-oxopropionic acid (366-77-8)

Guidance literature:

With aluminium trichloride; for 4h;

DOI:10.1002/hlca.19950780312

Reference yield: 90.6%

→ 4-(4-fluorophenyl)-4-oxopropionic acid (366-77-8)

Guidance literature:

Reference yield: 24.0%

3-(4-fluorophenyl)-2-hydroxycyclopent-2-en-1-one → (R)-2-(4-fluorophenyl)-5-oxotetrahydrofuran-2-carboxylic acid (917241-90-8) + (S)-2-(4-fluorophenyl)-5-oxotetrahydrofuran-2-carboxylic acid + 4-(4-fluorophenyl)-4-oxopropionic acid (366-77-8)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester; In decane; dichloromethane; at -20 ℃; for 114h; Title compound not separated from byproducts.;

DOI:10.1055/s-2006-950193

upstream raw materials:

succinic acid anhydride

fluorobenzene

bromperidol

4-(1H-imidazol-1-yl)-β-methyl-γ-oxobenzenebutanoic acid

Downstream raw materials:

4-(4-fluorophenyl)butanoic acid

ethyl 4-(4-fluorophenyl)-4-oxobutanoate

β-bromo-β-p-fluorobenzoyl-propionic acid

4oxo-4(4-pyrazol-1-yl-phenyl)butyric acid

Refernces

• 1、 Ali, Yakub,Alam, Mohammad Sarwar,Hamid, Hinna,Husain, Asif,Shafi, Syed,Dhulap, Abhijeet,Hussain, Firasat,Bano, Sameena,Kharbanda, Chetna,Nazreen, Syed,Haider, Saqlain. "Design and Synthesis of Butenolide-based Novel Benzyl Pyrrolones: Their TNF-α based Molecular Docking with in vivo and in vitro Anti-inflammatory Activity". . p. 619 - 625. Retrieved 2015.
• 2、 Karmakar, Ananta,Nimje, Roshan Y.,Silamkoti, Arundutt,Pitchai, Manivel,Basha, Mushkin,Singarayer, Christuraj,Ramasamy, Duraisamy,Babu, G. T. Venkatesh,Samikannu, Ramesh,Subramaniam, Srinath,Anjanappa, Prakash,Vetrichelvan, Muthalagu,Kumar, Hemantha,Dikundwar, Amol G.,Gupta, Anuradha,Gupta, Arun Kumar,Rampulla, Richard,Dhar, T. G. Murali,Mathur, Arvind. "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". . p. 1001 - 1014. Retrieved 2021/04/12.
• 3、 Khisal, Subuhi,Mishra, Ravinesh,Partap, Sangh,Siddiqui, Aness Ahmad,Yar, Mohammad Shahar. "Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues". . . Retrieved 2020/04/07.