3-(4-Fluorophenyl)-3-oxopropanoic acid

Base Information

• Chemical Name: 3-(4-Fluorophenyl)-3-oxopropanoic acid
• CAS No.: 80646-00-0
• Molecular Formula: C9H7FO3
• Molecular Weight: 182.151
• NSC Number: 126608
• DSSTox Substance ID: DTXSID60298865
• Wikidata: Q82040953
• Mol file: 80646-00-0.mol

Synonyms:3-(4-fluorophenyl)-3-oxopropanoic acid;2-(4-FLUOROBENZOYL)ACETIC ACID;80646-00-0;NSC126608;SCHEMBL904555;DTXSID60298865;WSWKUJUQMXOEQK-UHFFFAOYSA-N;MFCD01310984;AKOS006277598;NSC-126608;3-(4-fluorophenyl)-3-oxoproprionic acid;AS-78346;SY226864;CS-0372608

Chemical Property of 3-(4-Fluorophenyl)-3-oxopropanoic acid

Chemical Property:

• Vapor Pressure: 5.73E-06mmHg at 25°C
• Boiling Point: 365°Cat760mmHg
• PKA: 2.63±0.32(Predicted)
• Flash Point: 174.5°C
• PSA: 54.37000
• Density: 1.336g/cm³
• LogP: 1.48310
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.03792224
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

2-(4-Fluorobenzoyl)acetic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-(4-Fluorophenyl)-3-oxopropanoic acid

There total 4 articles about 3-(4-Fluorophenyl)-3-oxopropanoic 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: 56.0%

methyl 4-fluorobenzoyl acetate (63131-29-3) → 3-(4-fluorophenyl)-3-oxopropanoic acid (80646-00-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2018.02.077

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → 3-(4-fluorophenyl)-3-oxopropanoic acid (80646-00-0)

Guidance literature:

With water; amidase from Aspergillus nidulans A₁₁₄₅; In aq. phosphate buffer; at 30 ℃; for 0.5h; pH=8; Enzymatic reaction;

DOI:10.1021/acs.orglett.0c02426

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → 3-(4-fluorophenyl)-3-oxopropanoic acid (80646-00-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

1.2: Reflux; Inert atmosphere

2.1: sodium hydroxide / 12 h

With sodium hydride; sodium hydroxide; In 1,4-dioxane;

DOI:10.1002/cjoc.201700271

upstream raw materials:

methyl magnesium carbonate

1-(4-fluorophenyl)ethanone

methyl 4-fluorobenzoyl acetate

ethyl 3-(4'-fluorophenyl)-3-oxopropionate

Downstream raw materials:

C₂₃H₁₈FNO₃

(S)-2-[3-(4-fluorophenyl)-3-oxo-1-phenylpropyl]malononitrile

Refernces

• 1、 Liu, Mengting,Ohashi, Masao,Tang, Yi. "Engineered Biosynthesis of Fungal 4-Quinolone Natural Products". supporting information. p. 6637 - 6641. Retrieved 2020/09/02.
• 2、 Xu, Xiaolan,Chen, Huanhuan,He, Jianbo,Xu, Huajian. "Copper-Catalysed Decarboxylative Trifluoromethylation of β-Ketoacids". supporting information. p. 1665 - 1668. Retrieved 2017/10/05.