3-(Trifluoromethoxy)benzoic acid

Base Information

• Chemical Name: 3-(Trifluoromethoxy)benzoic acid
• CAS No.: 1014-81-9
• Molecular Formula: C8H5F3O3
• Molecular Weight: 206.121
• Hs Code.: 29189900
• European Community (EC) Number: 213-802-2
• DSSTox Substance ID: DTXSID00143906
• Nikkaji Number: J217.138D
• Wikidata: Q72511300
• ChEMBL ID: CHEMBL69854
• Mol file: 1014-81-9.mol

Synonyms:3-(Trifluoromethoxy)benzoic acid;1014-81-9;m-Trifluoromethoxybenzoic acid;Benzoic acid, 3-(trifluoromethoxy)-;m-(trifluoromethoxy)benzoic acid;3-trifluoromethoxybenzoic acid;3-(Trifluoromethoxy)benzoicacid;3-Trifluoromethoxy-benzoic acid;EINECS 213-802-2;MFCD00041501;alpha,alpha,alpha-Trifluoro-m-anisic Acid;3-Carboxy-alpha,alpha,alpha-trifluoroanisole;CHEMBL69854;SCHEMBL496275;3-trifluoromethoxy benzoic acid;DTXSID00143906;3-(trifluoromethoxy)-benzoic acid;3-Carboxy-A,A,A-trifluoroanisole;3-(Trifluoro methoxy)benzoic acid;3-(Trifluoromethoxy)benzoic acid;3-(Trifluoromethoxy)benzoic acid #;CL8097;STK503670;3-[(trifluoromethyl)oxy]benzoic acid;AKOS002663546;AC-4014;BS-4164;CS-W008406;DS-1084;3-(Trifluoromethoxy)benzoic acid, 97%;SY016224;AM20060102;FT-0613903;T2383;EN300-96355;W-108915;F0293-0013

Chemical Property of 3-(Trifluoromethoxy)benzoic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0.25mmHg at 25°C
• Melting Point: 89-92 °C(lit.)
• Refractive Index: 1.477
• Boiling Point: 243.8 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 101.2 °C
• PSA: 46.53000
• Density: 1.447 g/cm³
• LogP: 2.28340
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 206.01907850
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

3-(Trifluoromethoxy)benzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-R36/37/38
• Safety Statements: 26-36-37/39-S37/39-S26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)OC(F)(F)F)C(=O)O

Technology Process of 3-(Trifluoromethoxy)benzoic acid

There total 7 articles about 3-(Trifluoromethoxy)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: 85.0%

carbon dioxide (124-38-9,18923-20-1) + 1-bromo-3-(trifluoromethoxy)benzene (2252-44-0) → 3-(trifluoromethoxy)benzoic acid (1014-81-9)

Guidance literature:

1-bromo-3-(trifluoromethoxy)benzene; With n-butyllithium; In diethyl ether; hexane; at -75 ℃; for 0.75h;

carbon dioxide; In diethyl ether; hexane; at -78 ℃; Further stages.;

DOI:10.1002/1099-0690(200102)2001:4<691::AID-EJOC691>3.0.CO;2-A

Reference yield: 64.0%

carbon dioxide (124-38-9,18923-20-1) + m-chloro-α,α,α-trifluoromethoxybenzene (772-49-6) → 3-(trifluoromethoxy)benzoic acid (1014-81-9)

Guidance literature:

With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide; In N,N-dimethyl acetamide; at 100 ℃; for 12h; under 760.051 Torr; Inert atmosphere; Schlenk technique;

DOI:10.1039/d0cc06451c

Reference yield:

3-methyl-4-nitro-1-(trifluoromethoxy)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate + benzoic acid (65-85-0,8013-63-6) → 3-(trifluoromethoxy)benzoic acid (1014-81-9) + 2-(trifluoromethoxy)benzoic acid (1979-29-9) + 4-trifluoromethoxybenzoic acid (330-12-1)

Guidance literature:

With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In dichloromethane; acetonitrile; at 20 ℃; for 16h; Overall yield = 63 %Spectr.; regioselective reaction; Sealed tube; Irradiation;

DOI:10.1002/anie.201808495

upstream raw materials:

carbon dioxide

1-bromo-3-(trifluoromethoxy)benzene

benzoic acid

m-chloro-α,α,α-trifluoromethoxybenzene

Downstream raw materials:

2-nitro-5-(trifluoromethoxy)benzoic acid

N-[4-methyl-3-(4-pyrazin-2-yl-pyrimidin-2-ylamino)-phenyl]-3-trifluoromethoxybenzamide

N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-3-(trifluoromethoxy)-benzamide

methyl 4-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl-1-[3-(trifluoromethoxy)benzoyl]piperidine-4-carboxylate

Refernces

• 1、 Zheng, Weijia,Morales-Rivera, Cristian A.,Lee, Johnny W.,Liu, Peng,Ngai, Ming-Yu. "Catalytic C?H Trifluoromethoxylation of Arenes and Heteroarenes". . p. 9645 - 9649. Retrieved 2018.
• 2、 Zheng, Weijia,Lee, Johnny W.,Morales-Rivera, Cristian A.,Liu, Peng,Ngai, Ming-Yu. "Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C?H Trifluoromethoxylation". . p. 13795 - 13799. Retrieved 2018.
• 3、 -. "DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME". Page/Page column 43; 46; 56; 60. . Retrieved 2019/09/18.