455-24-3

Basic information

• Product Name: 4-(Trifluoromethyl)benzoic acid
• Synonyms: 4-(trifluoromethyl)-benzoicaci;Benzoic acid, 4-(trifluoromethyl)-;4-CARBOXYBENZOTRIFLUORIDE;4-(TRIFLUOROMETHYL)BENZOIC ACID;A,A,A-TRIFLUORO-P-TOLUIC ACID;ALPHA,ALPHA,ALPHA-TRIFLUORO-P-TOLUIC ACID;PTF-BOA;P-TRIFLUOROMETHYLBENZOIC ACID
• CAS NO: 455-24-3
• Molecular Formula: C₈H₅F₃O₂
• Molecular Weight: 190.12
• EINECS: 207-242-8
• Product Categories: blocks;Carboxes;Boronic Acid series;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;API intermediates;Benzotrifluoride Series;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 455-24-3.mol
• Article Data: 213

Chemical Properties

• Melting Point: 219-220 °C(lit.)
• Boiling Point: 247°C 753mm
• Flash Point: 247°C/753mm
• Appearance: White to slight gray/Fine Crystalline Powder
• Density: 1.3173 (estimate)
• Vapor Pressure: 7.81mmHg at 25°C
• Refractive Index: 1.449
• Storage Temp.: Store below +30°C.
• PKA: 3.69±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 2049241
• CAS DataBase Reference: 4-(Trifluoromethyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethyl)benzoic acid(455-24-3)
• EPA Substance Registry System: 4-(Trifluoromethyl)benzoic acid(455-24-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-24/25
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 455-24-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 455-24-3 differently. You can refer to the following data:
1. 4-(Trifluoromethyl)benzaldehyde is a reactant that has been used in the preparation of N,N'-(Arylmethylene)bisamides with cytotoxic activity as anti cancer agents.
2. 4-(Trifluoromethyl)benzoic acid was used in the synthesis of salicylanilide 4-(trifluoromethyl)benzoates via?N,N?-dicyclohexylcarbodiimide coupling in dry N,N-dimethylformamide. It was used as internal standard during the ultra trace analysis of fluorinated aromatic carboxylic acids by GC/MS method.

Chemical Properties

White to light yellow crystal powde

Definition

ChEBI: A benzoic acid carrying a 4-trifluoromethyl substituent.

InChI:InChI:1S/C8H5F3O2/c9-8(10,11)6-3-1-5(2-4-6)7(12)13/h1-4H,(H,12,13)

Synthetic route

4-Trifluoromethylbenzaldehyde (455-19-6) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;	99%
With oxygen; copper(II) acetate monohydrate; cobalt(II) diacetate tetrahydrate In water at 70℃; under 760.051 Torr; for 1h;	99%

1-(4-(trifluoromethyl)phenyl)ethane-1,2-diol (175605-64-8) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; under 760.051 Torr; Sealed tube;	99%

4-(trifluoromethyl)benzylic alcohol (349-95-1) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With manganese(II) bromide; silver carbonate; potassium hydroxide In 1,3,5-trimethyl-benzene at 50 - 165℃; for 2h; Schlenk technique; Inert atmosphere;	98%
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 72h;	97%
With 3,5-Lutidine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium persulfate; tris(2,2'‐bipyridine)ruthenium(II) hexafluorophosphate In water; acetonitrile at 20℃; for 48h; Sealed tube; Irradiation;	95%

4-methylbenzotrifluoride (6140-17-6) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With formic acid; 1,10-ethyliden-3-octyl-7-trifluoromethylalloxazinium chloride; oxygen In acetonitrile at 40℃; for 24h; Irradiation;	98%
With cerium(III) chloride; 1,1,1-trichloroethanol; oxygen In acetonitrile at 60℃; Irradiation;	90%
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry;	87%
With pyridine; dipotassium peroxodisulfate; oxygen In acetonitrile at 80℃; under 760.051 Torr; for 16h; Green chemistry;	72%

methyl 4-(trifluoromethyl)benzoate (2967-66-0) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With iodine; aluminium In acetonitrile at 80℃; for 18h;	98%
With lithium hydroxide monohydrate; water In ethanol at 25℃; for 12h;	94.8%
With methanol; water; sodium hydroxide at 20℃; for 2h;	68.4%

carbon dioxide (124-38-9) + 5,5-dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3,2]dioxaborinane (501374-30-7) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3,2]dioxaborinane With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;	97%
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;	92%
With (1,3-bis(2,6-diisopropyl-4-(morpholinomethyl)phenyl)imidazolidin-2-ylidene)copper(I) bromide; potassium tert-butylate In tetrahydrofuran under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;	90%
With 1,3-bis-(diphenylphosphino)propane; cesium fluoride; [Rh(OH)(cod)]2 In 1,4-dioxane at 60℃;	76%
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3,2]dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In 1,4-dioxane at 100℃; under 15201 Torr; for 8h; Inert atmosphere; Autoclave; Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;	74%

methyl 3-oxo-3-(4-(trifluoromethyl)phenyl) propanedithioate (1448887-34-0) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With sodium hydroxide In water at 100℃; for 9h; Reflux; chemoselective reaction;	97%

carbon monoxide (201230-82-2) + 4-Iodobenzotrifluoride (455-13-0) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With amphiphilic resin-supported phosphine-palladium; water; potassium carbonate at 25℃; under 760 Torr; for 12h; hydroxycarbonylation;	96%
With water; potassium carbonate In acetonitrile; tert-butyl alcohol at 100℃; under 3750.38 Torr; for 0.0161111h;	96%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 7h;	82%
With water; palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; under 11251.1 Torr; Flow reactor;	78%
With water; sodium carbonate; palladium diacetate at 20 - 165℃; under 10501.1 - 22502.3 Torr; for 0.333333h; microwave irradiation;	59%

1-(4-trifluorophenyl)ethanol (1737-26-4) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With sodium nitrate; water; oxygen In dimethyl sulfoxide at 130℃; for 24h;	96%

4-trifluoromethyl-benzoyl fluoride (368-94-5) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With water at 20℃; Temperature; Reflux;	95.4%

1-(4-methoxyphenyl)-2-[4-(trifluoromethyl)phenyl]ethanone (181308-89-4) → 4-trifluoromethylbenzoic acid (455-24-3) + 4-methoxybenzoic acid (100-09-4)

Conditions	Yield
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction;	A 90% B 93%

carbon monoxide (201230-82-2) + 4-chlorobenzotrifluoride (98-56-6) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; water; palladium diacetate; potassium carbonate In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 15h;	92%
With potassium hydroxide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In water for 48h; Heating;	500 % Turnov.

carbon dioxide (124-38-9) + p-trifluoromethylphenyl bromide (402-43-7) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 2-(diphenylphosphino)-2’(3-(dimethylamino)-3-oxopropyl)-6’-(3-(icosyloxy)-3-oxopropyl)biphenyl; water; palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique; Irradiation;	92%
Stage #1: p-trifluoromethylphenyl bromide With bromobenzene; trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; zinc In acetonitrile Inert atmosphere; Stage #2: carbon dioxide With palladium diacetate; tricyclohexylphosphine In tetrahydrofuran; acetonitrile at 0℃; under 760.051 Torr; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate; acetonitrile	90%
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 4h; Electrolysis;	78%

4-Trifluoromethylbenzaldehyde (455-19-6) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → 4-trifluoromethylbenzoic acid (455-24-3) + ethyl (E)-4-trifluoromethylcinnamate (101466-85-7, 128408-03-7)

Conditions	Yield
Stage #1: 4-Trifluoromethylbenzaldehyde; diethoxyphosphoryl-acetic acid ethyl ester With potassium carbonate for 6h; Horner-Wadsworth-Emmons olefination; Neat (no solvent); high-speed ball milling; Stage #2: With Oxone for 12h; Neat (no solvent); high-speed ball milling; optical yield given as %de; diastereoselective reaction;	A n/a B 91%

carbon dioxide (124-38-9) + 4-(trifluoromethyl)phenylsulfurofluoridate → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;	91%

ethyl 4-(trifluoromethyl)benzoate (583-02-8) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With water; potassium hydroxide at 115℃; for 1h;	90%

(±)-1,2-bis(4-(trifluoromethyl)phenyl)ethane-1,2-diol (199166-26-2) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
Stage #1: (±)-1,2-bis(4-(trifluoromethyl)phenyl)ethane-1,2-diol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; chemoselective reaction;	89%
Stage #1: (±)-1,2-bis(4-(trifluoromethyl)phenyl)ethane-1,2-diol With 2,3,4,5,6-pentamethyliodobenzene; oxygen; isobutyraldehyde In 1,2-dichloro-ethane under 760.051 Torr; for 24h; Stage #2: With sodium chlorite; 2-methyl-but-2-ene In aq. phosphate buffer; 1,2-dichloro-ethane; tert-butyl alcohol at 25℃; for 14h;	79%
With oxygen In dichloromethane at 20℃; under 760.051 Torr; for 12h; Irradiation;	78%

carbon dioxide (124-38-9) + 4-Iodobenzotrifluoride (455-13-0) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h;	88%

p-trifluoromethylbenzamide (1891-90-3) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With acetic acid; isopentyl nitrite at 80℃; for 24h; Inert atmosphere;	86%

2-(4-trifluoromethylphenyl)ethanol (2968-93-6) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 750.075 Torr; for 12h; chemoselective reaction;	86%

carbon monoxide (201230-82-2) + p-trifluoromethylphenyl bromide (402-43-7) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With water; potassium carbonate In acetonitrile; tert-butyl alcohol at 120℃; under 30003 Torr; for 7h;	85%

carbon dioxide (124-38-9) + p-trifluoromethylphenyl bromide (402-43-7) → α,α,α-trifluorotoluene (98-08-8) + 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 10h; Ambient temperature; electrochemically;	A 2.4 mmol B 84%

formic acid (64-18-6) + p-trifluoromethylphenyl bromide (402-43-7) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	84%
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 24h; Temperature; Inert atmosphere;	80%

4-(trifluoromethyl)mandelic acid (395-35-7) → 4-Trifluoromethylbenzaldehyde (455-19-6) + 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With sodium hydroxide; oxygen; CoCl2 In water; dimethyl sulfoxide at 125℃; under 760.051 Torr; for 24h; Title compound not separated from byproducts.;	A 17% B 83%

carbon dioxide (124-38-9) + sodium 4-trifluoromethylbenzenesulfinate → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium tert-butylate In dimethyl sulfoxide at 140℃; under 750.075 Torr; for 3h; Schlenk technique; Sealed tube;	83%

carbon dioxide (124-38-9) + Sodium; 4-trifluoromethyl-benzenesulfonate (360-27-0) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
Stage #1: carbon dioxide; Sodium; 4-trifluoromethyl-benzenesulfonate With copper(l) iodide; potassium tert-butylate; o-phenanthroline In dimethyl sulfoxide at 140℃; under 760.051 Torr; for 12h; Schlenk technique; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide Schlenk technique;	81%

carbon dioxide (124-38-9) + dimethyl(4-(trifluoromethyl)phenyl)sulfonium trifluoromethanesulfonate → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With 2.9-dimethyl-1,10-phenanthroline; neocuproine; zinc In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h;	81%

1-(4-(trifluoromethyl)phenyl)cyclohexanol (29480-13-5) → 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With iron(III) chloride; cerium(III) chloride; tetrabutyl-ammonium chloride; oxygen In acetonitrile at 20℃; under 760.051 Torr; for 24h; Schlenk technique; Irradiation;	81%

carbon dioxide (124-38-9) + 4-chlorobenzotrifluoride (98-56-6) → α,α,α-trifluorotoluene (98-08-8) + 4-trifluoromethylbenzoic acid (455-24-3)

Conditions	Yield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A);	A 3 % Chromat. B 80%

4-trifluoromethylbenzoic acid (455-24-3) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
With thionyl chloride Reflux;	100%
With thionyl chloride for 2h; Reflux;	100%
Stage #1: 4-trifluoromethylbenzoic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h; Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h;	100%

4-trifluoromethylbenzoic acid (455-24-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-4-trifluoromethylbenzamide (116332-61-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	100%
Stage #1: 4-trifluoromethylbenzoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 23℃; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 2h;	95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;	95%

n-heptan1ol (111-70-6) + 4-trifluoromethylbenzoic acid (455-24-3) → heptyl 4-(trifluoromethyl)benzoate (959086-76-1)

Conditions	Yield
With Candida antarctica lipase B immobilised in a macroporous DVB crosslinked polymer (Novozym 435) In cyclohexane at 80℃; for 24h; Enzymatic reaction;	100%

4-trifluoromethylbenzoic acid (455-24-3) + C21H33N3O (1619984-56-3) → N-((2R,3S,4S,4aS)-3,4a,8,8-tetramethyl-4-((4-(trifluoromethyl)benzamido)methyl)-decahydronaphthalen-2-yl)nicotinamide (1619983-84-4)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere;	100%

4-trifluoromethylbenzoic acid (455-24-3) + tetramethyl ammoniumhydroxide (75-59-2) → C8H4F3O2(1-)*C4H12N(1+)

Conditions	Yield
With water In ethanol at 0 - 20℃; for 0.0833333h;	100%

4-trifluoromethylbenzoic acid (455-24-3) → 4-(trifluoromethyl)benzylic alcohol (349-95-1)

Conditions	Yield
With C25H42N6Rh(1+)*CF3O3S(1-); phenylsilane In tetrahydrofuran at 30℃; for 20h; Inert atmosphere;	99%
Stage #1: 4-trifluoromethylbenzoic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667h; Stage #2: With sodium tetrahydroborate In water; ethyl acetate at 0℃; for 0.466667h;	90%
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 100℃; under 60006 Torr; for 22h;	82%

2,2-dimethyl-propanol-1 (75-84-3) + 4-trifluoromethylbenzoic acid (455-24-3) → 2,2-dimethyl-1-propanol-mono(p-trifluoro-methylbenzoate)

Conditions	Yield
With sulfuric acid In toluene	99%
With sulfuric acid In toluene	99%
With sulfuric acid In toluene	99%

4-trifluoromethylbenzoic acid (455-24-3) + phenylboronic acid (98-80-6) → phenyl[4-(trifluoromethyl)phenyl]methanone (728-86-9)

Conditions	Yield
With dimethyl dicarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 6h;	99%
Stage #1: 4-trifluoromethylbenzoic acid With di(succinimido) carbonate; sodium carbonate; tricyclohexylphosphine; palladium(II) hexafluoroacetylacetonate In tetrahydrofuran at 60℃; Stage #2: phenylboronic acid In tetrahydrofuran at 60℃; for 20h; Further stages.;	89%
Stage #1: 4-trifluoromethylbenzoic acid With potassium phosphate In 1,4-dioxane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With 2-chloro-1,3-dimethylimidazolinium chloride In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #3: phenylboronic acid With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90℃; for 16h; Inert atmosphere; Sealed tube;	62%
With 2,2-dimethylpropanoic anhydride; tricyclohexylphosphine In tetrahydrofuran; water at 60℃; for 16h;	40%

4-trifluoromethylbenzoic acid (455-24-3) + benzyl alcohol (100-51-6) → 4-trifluoromethyl-benzoic acid benzyl ester

Conditions	Yield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;	99%
With 2-butyl-1,3-diphenyl-1,3,2-diazaphospholidine; 1,1'-azodicarbonyl-dipiperidine In 1,2-dichloro-ethane at 40℃; under 760.051 Torr; Mitsunobu Displacement;	89%

4-trifluoromethylbenzoic acid (455-24-3) + benzylamine (100-46-9) → N-benzyl-4-trifluoromethylbenzamide

Conditions	Yield
With 14C2H2F3O(1-)*6C4H8O*La2Na8(14+) at 80℃; for 6h; Inert atmosphere;	99%
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;	99%
With tetrachloromethane; Bis(p-nitrophenyl) phosphate; 3-Methyl-1-phenyl-2-phospholene 1-oxide In toluene at 110℃; for 20h; Green chemistry;	98%

4-trifluoromethylbenzoic acid (455-24-3) + aniline (62-53-3) → N-phenyl 4-trifluoromethylbenzamide (347-80-8)

Conditions	Yield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	99%
With 2,4,6-trimethyl-pyridine; dmap; carbon tetrabromide In N,N-dimethyl-formamide for 0.5h; UV-irradiation;	94 %Spectr.

para-iodoanisole (696-62-8) + 4-trifluoromethylbenzoic acid (455-24-3) → 2,6-bis(4-methoxyphenyl)-4-(trifluoromethyl)benzoic acid

Conditions	Yield
With C30H54N6Ru(2+)*2BF4(1-); potassium perfluoro-tert-butoxide; potassium carbonate at 140℃; for 24h; Glovebox; Inert atmosphere;	99%

4-trifluoromethylbenzoic acid (455-24-3) + methyl 5-amino-4'-carbamoyl-[1,1'-biphenyl]-3-carboxylate → methyl 4'-carbamoyl-5-(4-(trifluoromethyl)benzamido)-[1,1'-biphenyl]-3-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 15h;	99%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h;	99%

10-Undecen-1-ol (112-43-6) + 4-trifluoromethylbenzoic acid (455-24-3) → undec-10-en-1-yl 4-(trifluoromethyl)benzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	99%

4-trifluoromethylbenzoic acid (455-24-3) → potassium 4-(trifluoromethyl)benzoate (1195761-03-5)

Conditions	Yield
With potassium tert-butylate In ethanol at 20℃; Inert atmosphere;	98%
With potassium tert-butylate In ethanol at 20℃; for 3h;	98%

4-trifluoromethylbenzoic acid (455-24-3) + benzyl azide (622-79-7) → N-benzyl-4-trifluoromethylbenzamide

Conditions	Yield
With phenylsilane; triphenylphosphine In toluene at 20 - 60℃; for 21h; Reagent/catalyst; Staudinger Azide Reduction; Inert atmosphere; chemoselective reaction;	98%
With 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane; triethylamine In chlorobenzene at 20 - 130℃; for 14h;	85%

4-trifluoromethylbenzoic acid (455-24-3) + p-aminoethylbenzoate (94-09-7) → ethyl 4-(4-(trifluoromethyl)benzamido)benzoate

Conditions	Yield
Stage #1: 4-trifluoromethylbenzoic acid With dichlorotriphenylphosphorane In chloroform at 20℃; for 0.25h; Inert atmosphere; Stage #2: p-aminoethylbenzoate In chloroform at 100℃; Inert atmosphere; Irradiation;	98%

4-trifluoromethylbenzoic acid (455-24-3) + phenylmagnesium bromide (100-58-3) → phenyl[4-(trifluoromethyl)phenyl]methanone (728-86-9)

Conditions	Yield
Stage #1: 4-trifluoromethylbenzoic acid With tert-butylmagnesium chloride In tetrahydrofuran; toluene at 0℃; for 0.25h; Inert atmosphere; Stage #2: phenylmagnesium bromide With diisopropylaminomagnesium chloride lithium chloride In tetrahydrofuran; toluene at 0 - 20℃; for 3.25h; Inert atmosphere; Sonication;	98%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-trifluoromethylbenzoic acid (455-24-3) → 2,5-dioxopyrrolidin-1-yl 4-(trifluoromethyl)benzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	97%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 3h; Inert atmosphere;	67%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃; for 2h;

4-trifluoromethylbenzoic acid (455-24-3) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(4-(trifluoromethyl)benzoyl)piperazine-1-carboxylate (1327712-44-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	97%
Stage #1: 4-trifluoromethylbenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-t-Butoxycarbonylpiperazine In N,N-dimethyl-formamide at 20℃; for 16h;

4-trifluoromethylbenzoic acid (455-24-3) + Propargylamine (2450-71-7) → 4-(trifluoromethyl)-N-(prop-2-yn-1-yl)benzamide (1250690-13-1)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane	97%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Concentration; Inert atmosphere;	93.2%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	70.5%

4-trifluoromethylbenzoic acid (455-24-3) + bis(pinacol)diborane (73183-34-3) → 4-trifluoromethylphenylboronic acid pinacol ester (214360-65-3)

Conditions	Yield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h;	97%
With biphenyl; naphthalene-1,4-dicarbonitrile In water; acetonitrile at 30℃; for 6h; Inert atmosphere; UV-irradiation;	34%

4-trifluoromethylbenzoic acid (455-24-3) + Benzhydrylamine (91-00-9) → N-benzhydryl-4-(trifluoromethyl)benzamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique;	97%

Upstream product

• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 98-08-8 α,α,α-trifluorotoluene 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 151-50-8 potassium cyanide 
• 402-13-1 2-amino-4-trifluoromethylbenzoic acid 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 2314-97-8 iodotrifluoromethane 
• 619-58-9 4-iodobenzoic acid 
• 124-38-9 carbon dioxide 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 146397-87-7 p-(trifluoromethyl)phenyl trifluoromethanesulfonate 
• 127843-54-3 C₉H₇F₃N₂O₃ 
• 77826-14-3 N,N-Diphenyl-4-trifluoromethyl-benzamide 

Downstream Products

• 1204296-05-8 methyl 4-trifluoromethylcyclohexanecarboxylate 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 100467-75-2 N-(3-Imidazol-1-yl-butyl)-4-trifluoromethyl-benzamide 
• 104393-35-3 1,3-Dimethyl-5-(4-trifluoromethyl-phenyl)-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 320-94-5 2-nitro-4-trifluoromethylbenzoic acid 
• 116965-16-3 3-nitro-4-(trifluoromethyl)benzoic acid 
• 368-94-5 4-trifluoromethyl-benzoyl fluoride 
• 1647-85-4 bis(p-trifluoromethylbenzoyl) peroxide 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 87427-94-9 (4-Trifluoromethyl-benzoylamino)-acetic acid ethyl ester 
• 205236-58-4 (S)-4-[(S)-3-[4-(Di-tert-butoxy-phosphoryloxy)-phenyl]-2-(4-trifluoromethyl-benzoylamino)-propionylamino]-4-dipentylcarbamoyl-butyric acid tert-butyl ester 
• 106263-53-0 ethyl 3-oxo-3-(4-(trifluoromethyl)phenyl)propanoate 
• 21221-91-0 4,4'-bis(trifluoromethyl)benzophenone 
• 106376-16-3 p-trifluoromethylbenzoic acid phenyl ester 

Relevant articles and documents

Acid/base-catalyzed ester hydrolysis in near-critical water

Hydrolyses of substituted benzoic acid esters in near-critical water (250-300°C) show autocatalytic kinetic behavior and surprisingly give the same rate constant regardless of substituent, suggesting that an acid-catalyzed mechanism predominates under our reaction conditions.

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

Mechanistic studies into visible light-driven carboxylation of aryl halides/triflates by the combined use of palladium and photoredox catalysts

The reaction mechanism of palladium-catalyzed visible light-driven carboxylation of aryl halides and triflates with a photoredox catalyst was examined in detail. Experimental and theoretical studies indicated that the active species for photoredox- catalyzed reduction was cationic ArPd(II)+ species to generate nucleophilic ArPd(I) or its further reduced ArPd(0)- species, which reacted with CO2 to give carboxylic acids. Hydrodehalogenated compounds, main byproducts in this carboxylation, were thought to be generated by protonation of these reduced species.