3,5-Bis(trifluoromethyl)benzoic acid

Base Information

• Chemical Name: 3,5-Bis(trifluoromethyl)benzoic acid
• CAS No.: 725-89-3
• Molecular Formula: C9H4F6O2
• Molecular Weight: 258.12
• Hs Code.: 29163990
• European Community (EC) Number: 211-970-1
• NSC Number: 88282
• UNII: NN52L84T3A
• DSSTox Substance ID: DTXSID20222808
• Nikkaji Number: J73.879D
• Wikidata: Q72447190
• ChEMBL ID: CHEMBL3728871
• Mol file: 725-89-3.mol

Synonyms:3,5-Bis(trifluoromethyl)benzoic acid;725-89-3;BENZOIC ACID, 3,5-BIS(TRIFLUOROMETHYL)-;3,5-di(Trifluoromethyl)benzoic acid;Bis(3,5-trifluoromethyl)benzoic acid;C9H4F6O2;EINECS 211-970-1;NSC 88282;BRN 2058600;NN52L84T3A;MFCD00000388;NSC-88282;3,5-bis(trifluoromethyl) benzoic acid;3,5-bis-(trifluoromethyl)benzoic acid;3.5-Bis(trifluoromethyl)benzoic acid;NSC88282;Maybridge1_003411;UNII-NN52L84T3A;SCHEMBL503980;CHEMBL3728871;HMS551D01;HVFQJWGYVXKLTE-UHFFFAOYSA-;TORCETRAPIB METABOLITE M1;DTXSID20222808;3,5-bistrifluoromethylbenzoic acid;Cyclohexanecarboxaldehyde, 1-propyl-;3,5-bis-trifluoromethyl-benzoic acid;3,5-bis trifluoro methyl benzoic acid;3,5-bis(trifluoromethyl)-benzoic acid;AKOS000120436;3,5-Di-(trifluoromethyl) benzoic acid;AB00127;AC-3901;AM61649;CCG-240220;CS-W012544;PS-7386;3,5-bis-(trifluoromethyl)-benzoic acid;LS-36193;SY016218;3,5-Bis(trifluoromethyl)benzoic acid, 98%;B1420;FT-0614456;EN300-17196;D70169;J-511237;W-104483;Z56899078;F0001-1846

Chemical Property of 3,5-Bis(trifluoromethyl)benzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0537mmHg at 25°C
• Melting Point: 142-143 °C(lit.)
• Boiling Point: 223.9 °C at 760 mmHg
• PKA: 3.34±0.10(Predicted)
• Flash Point: 89.2 °C
• PSA: 37.30000
• Density: 1.527 g/cm³
• LogP: 3.42240
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO, Methanol
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 258.01154834
• Heavy Atom Count: 17
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

3,5-Bis(trifluoromethyl)benzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1C(F)(F)F)C(F)(F)F)C(=O)O
• Uses: 3,5-Bis(trifluoromethyl)benzoic acid is a useful synthetic intermediate, and is a derivative of Benzoic acid (B203900). 3,5-Bis(trifluoromethyl)benzoic acid has also been identified as a major metabolite of a series of 3,5-bis(trifluoromethyl)benzyl ethers in vitro, and is hypothesized to result via oxidation of the benzylic position.

Technology Process of 3,5-Bis(trifluoromethyl)benzoic acid

There total 26 articles about 3,5-Bis(trifluoromethyl)benzoic 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: 94.0%

carbon dioxide (124-38-9,18923-20-1) + 3,6-bis(trifluoromethyl)bromobenzene (328-70-1) → 3,5-bistrifluoromethylbenzoic acid (725-89-3)

Guidance literature:

With n-butyllithium; In diethyl ether; at -75 ℃;

DOI:10.1002/cber.19961290219

Reference yield: 91.0%

3,5-bis(trifluoromethyl)benzylchloride (75462-61-2) → 3,5-bistrifluoromethylbenzoic acid (725-89-3)

Guidance literature:

With iron(III) sulfate; water; In acetonitrile; at 20 ℃; for 16h; UV-irradiation;

DOI:10.1016/j.tet.2021.132298

Reference yield: 85.0%

2-hydroxy-4-phenylbutanenitrile (121054-03-3) + 3,5-bis(trifluoromethyl)benzoic anhydride (155929-90-1) → 3,5-bistrifluoromethylbenzoic acid (725-89-3) + 1-cyano-3-phenylpropyl 3,5-bis(trifluoromethyl)benzoate

Guidance literature:

2-hydroxy-4-phenylbutanenitrile; 3,5-bis(trifluoromethyl)benzoic anhydride; With triethylamine; In dichloromethane; at 20 ℃; for 2h;

With hydrogenchloride; In water;

DOI:10.3762/bjoc.10.223

upstream raw materials:

carbon dioxide

3,6-bis(trifluoromethyl)bromobenzene

1,3-bis(trifluoromethyl)benzene

3,5-bis(trifluoromethyl)benzoyl fluoride

Downstream raw materials:

3,5-bis(trifluoromethyl)benzoic anhydride

3,5-bis-(trifluoromethyl)benzoic acid hydrazide

(2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine

copper(I) 3,5-bis(trifluoromethyl)benzoate

Refernces

• 1、 Heinz, Werner R.,Staude, Dominik,Mayer, David,Bunzen, Hana,Fischer, Roland A.. "Scrutinizing ligand exchange reactions in the formation of the precious group metal-organic framework RuII,II-HKUST-1: The impact of diruthenium tetracarboxylate precursor and modulator choice". supporting information. p. 5226 - 5235. Retrieved 2021/04/26.
• 2、 Osako, Takao,Kaiser, Reinhard,Torii, Kaoru,Uozumi, Yasuhiro. "Aqueous Flow Hydroxycarbonylation of Aryl Halides Catalyzed by an Amphiphilic Polymer-Supported Palladium-Diphenylphosphine Catalyst". . p. 961 - 966. Retrieved 2019/05/10.