2-Fluorobiphenyl-4-carboxylic acid

Base Information

• Chemical Name: 2-Fluorobiphenyl-4-carboxylic acid
• CAS No.: 137045-30-8
• Molecular Formula: C13H9FO2
• Molecular Weight: 216.212
• European Community (EC) Number: 623-980-7
• UNII: Z6XXN3O38O
• Nikkaji Number: J425.320E
• Wikidata: Q27295089
• Mol file: 137045-30-8.mol

Synonyms:137045-30-8;2-Fluorobiphenyl-4-carboxylic acid;2-Fluoro-[1,1'-biphenyl]-4-carboxylic acid;3-fluoro-4-phenylbenzoic acid;Z6XXN3O38O;[1,1'-Biphenyl]-4-carboxylic acid, 2-fluoro-;MFCD05664334;UNII-Z6XXN3O38O;(1,1'-BIPHENYL)-4-CARBOXYLIC ACID, 2-FLUORO-;Flurbiprofen Impurity E;SCHEMBL2041007;3-fluoro-4-phenyl-benzoic acid;FLURBIPROFEN EP IMPURITY E;PFKITESTTSWHMP-UHFFFAOYSA-N;BCP33192;AKOS010379465;CS-W014852;2-Fluorobiphenyl-4-carboxylic acid 97%;SY283530;WS-01239;2-Fluorobiphenyl-4-carboxylic acid, 97%;3-FLUORO-4-BIPHENYLCARBOXYLIC ACID;2-Fluoro-[1,1'-biphenyl]-4-carboxylicacid;FLURBIPROFEN IMPURITY E [EP IMPURITY];EN300-5504081;Q27295089;Z756936500

Chemical Property of 2-Fluorobiphenyl-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 5.21E-06mmHg at 25°C
• Melting Point: 223-227 °C(lit.)
• Boiling Point: 366.3°C at 760 mmHg
• PKA: 3.85±0.10(Predicted)
• Flash Point: 175.3°C
• PSA: 37.30000
• Density: 1.261g/cm³
• LogP: 3.19090
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 216.05865769
• Heavy Atom Count: 16
• Complexity: 248

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Fluorobiphenyl-4-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C=C(C=C2)C(=O)O)F
• Uses: 2-Fluorobiphenyl-4-carboxylic Acid is an impurity of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic. Flurbiprofen impurity E.

Technology Process of 2-Fluorobiphenyl-4-carboxylic acid

There total 6 articles about 2-Fluorobiphenyl-4-carboxylic 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: 70.0%

carbon dioxide (124-38-9,18923-20-1) + 1-bromo-3-fluoro-4-phenylbenzene (41604-19-7) + potassium carbonate (584-08-7) → 2-fluoro-4-biphenylacetic acid (137045-30-8)

Guidance literature:

With nickel(II) bromide dimethoxyethane; 2.9-dimethyl-1,10-phenanthroline; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C₆₀H₃₆N₂; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Molecular sieve; Irradiation;

DOI:10.1002/anie.201706724

Reference yield: 61.0%

C18H19FO → 2-fluoro-4-biphenylacetic acid (137045-30-8)

Guidance literature:

With iron(III) chloride; cerium(III) chloride; tetrabutyl-ammonium chloride; oxygen; In acetonitrile; at 20 ℃; for 24h; under 760.051 Torr; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.1c00556

Reference yield:

4-bromo-3-fluorobenzoic acid (153556-42-4) + phenylboronic acid (98-80-6) → 2-fluoro-4-biphenylacetic acid (137045-30-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 110 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.ejmech.2019.05.047

upstream raw materials:

carbon dioxide

1-bromo-3-fluoro-4-phenylbenzene

potassium carbonate

4-bromo-3-fluorobenzoic acid

Downstream raw materials:

4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]phenylmethanol

2-fluorobiphenyl-4-carboxylic acid[hydroxyimino(4-hydroxymethylphenyl)methyl]amide

1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(piperidine-1-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester

1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethylpropanoyloxymethyl) ester

Refernces

• 1、 Zhang, Zongnan,Zhang, Guoxiang,Xiong, Ni,Xue, Ting,Zhang, Junjie,Bai, Lu,Guo, Qinyue,Zeng, Rong. "Oxidative α-C-C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O2at Room Temperature via Iron Photocatalysis". supporting information. p. 2915 - 2920. Retrieved 2021/05/05.
• 2、 Zhao, Shizhen,Zhao, Liyu,Zhang, Xiangqian,Wei, Peng,Wu, Mengya,Su, Xin,Sun, Bin,Zhao, Dongmei,Cheng, Maosheng. "Design, synthesis and evaluation of biphenyl imidazole analogues as potent antifungal agents". supporting information. p. 2448 - 2451. Retrieved 2019/07/30.