4'-Trifluoromethyl-biphenyl-3-carboxylic acid

Base Information

• Chemical Name: 4'-Trifluoromethyl-biphenyl-3-carboxylic acid
• CAS No.: 199528-28-4
• Molecular Formula: C₁₄H₉F₃O₂
• Molecular Weight: 266.219
• Hs Code.: 2916399090
• European Community (EC) Number: 672-174-1
• DSSTox Substance ID: DTXSID40382236
• Wikidata: Q82173546
• Mol file: 199528-28-4.mol

Synonyms:199528-28-4;4'-Trifluoromethyl-biphenyl-3-carboxylic acid;4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-carboxylic acid;3-[4-(trifluoromethyl)phenyl]benzoic Acid;4'-(Trifluoromethyl)biphenyl-3-carboxylic acid;4'-trifluoromethylbiphenyl-3-carboxylic acid;4'-trifluoromethyl [1,1'-biphenyl]-3-carboxylic acid;4/'-TRIFLUOROMETHYL-BIPHENYL-3-CARBOXYLIC ACID;4'-(trifluoromethyl)[1,1'-biphenyl]-3-carboxylic acid;SCHEMBL177453;4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-carboxylicacid;DTXSID40382236;MFCD03424604;AKOS004117566;AS-2109;3-(4-trifluoromethylphenyl)benzoic acid;3-(4-Trifluoromethylphenyl)-benzoic acid;BP-11309;BB 0222373;CS-0207284;FT-0643859;4`-Trifluoromethyl-biphenyl-3-carboxylic acid;4'-(trifluoromethyl)-3-biphenylcarboxylic acid;[1,1'-Biphenyl]-3-carboxylic acid, 4'-(trifluoromethyl)-;[1,1'-Biphenyl]-3-carboxylicacid,4'-(trifluoromethyl)-;4'-Trifluoromethyl-biphenyl-3-carboxylic acid, AldrichCPR;4?E per thousand-Trifluoromethylbiphenyl-3-carboxylic acid

Chemical Property of 4'-Trifluoromethyl-biphenyl-3-carboxylic acid

Chemical Property:

• Boiling Point: 377.5°Cat760mmHg
• PKA: 4.01±0.10(Predicted)
• Flash Point: 182.1°C
• PSA: 37.30000
• Density: 1.326g/cm³
• LogP: 4.07060
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 266.05546401
• Heavy Atom Count: 19
• Complexity: 319

Purity/Quality:

97% ^*data from raw suppliers

4''-(Trifluoromethyl)-3-biphenylcarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)C(=O)O)C2=CC=C(C=C2)C(F)(F)F
• Uses: 4''-(Trifluoromethyl)-3-biphenylcarboxylic Acid functions as a reagent in the scalable development of GPR40 receptor agonist AMG 837. A potential antidiabetic agent.

Technology Process of 4'-Trifluoromethyl-biphenyl-3-carboxylic acid

There total 1 articles about 4'-Trifluoromethyl-biphenyl-3-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: 91.0%

m-bromobenzoic acid (585-76-2) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 4'-(trifluoromethyl)[1,1'-biphenyl]-3-carboxylic acid (199528-28-4)

Guidance literature:

With 5%-palladium/activated carbon; sodium carbonate; In water; isopropyl alcohol; at 75 ℃; for 3h; Large scale reaction;

DOI:10.1021/op1003055

Reference yield: 99.0%

4'-(trifluoromethyl)[1,1'-biphenyl]-3-carboxylic acid (199528-28-4) → (4'-Trifluoromethyl-biphenyl-3-yl)-methanol (126485-55-0)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; Trimethyl borate; In tetrahydrofuran; at 41 - 49 ℃; for 4h; Large scale reaction;

DOI:10.1021/op1003055

Reference yield:

4'-(trifluoromethyl)[1,1'-biphenyl]-3-carboxylic acid (199528-28-4) → [3H]-AMG 837 (865231-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; Trimethyl borate / tetrahydrofuran / 4 h / 41 - 49 °C / Large scale reaction

2: sulfurous dibromide; triethylamine / toluene / 2.8 h / 35 - 40 °C / Large scale reaction

3: tetra-n-butylphosphonium hydroxide / tetrahydrofuran; water / 21 h / -5 - 20 °C

With sodium tetrahydroborate; sulfurous dibromide; boron trifluoride-tetrahydrofuran complex; Trimethyl borate; tetra-n-butylphosphonium hydroxide; triethylamine; In tetrahydrofuran; water; toluene;

DOI:10.1021/op1003055

upstream raw materials:

m-bromobenzoic acid

4-trifluoromethylphenylboronic acid

Downstream raw materials:

(4'-Trifluoromethyl-biphenyl-3-yl)-methanol

N-((4-(phenoxymethyl)phenyl)sulfonyl)-4'-(trifluoromethyl)[1,1'-biphenyl]-3-carboxamide

(3S)-3-[4-(4'-trifluoromethyl-biphenyl-3-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester

[3H]-AMG 837