88-17-5

Basic information

• Product Name: 2-Aminobenzotrifluoride
• Synonyms: α,α,α-Trifluoro-o-toluidine, 2-Aminobenzotrifluoride;2-Aminobenzotrifluoride ,99%;o-Amino-α,α,α-trifluorotoluene;2-(Trifluoromethyl)aniline,α,α,α-Trifluoro-o-toluidine, 2-Aminobenzotrifluoride;2-Aminobenzotrifluor;2-AMinobenzotrifluoride, 99% 100ML;2-AMinobenzotrifluoride, 99% 5ML;2-(Trifluoromethyl)aniline alpha,alpha,alpha-Trifluoro-o-toluidine
• CAS NO: 88-17-5
• Molecular Formula: C₇H₆F₃N
• Molecular Weight: 161.12
• EINECS: 201-806-7
• Product Categories: API intermediates;Amines;Building Blocks;C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;amine;Pyridines;Anilines, Aromatic Amines and Nitro Compounds;Aromatic Halides (substituted)
• Mol File: 88-17-5.mol
• Article Data: 47

Chemical Properties

• Melting Point: 34 °C(lit.)
• Boiling Point: 170-173 °C(lit.)
• Flash Point: 131 °F
• Appearance: Clear colorless to light amber/Liquid
• Density: 1.282 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.1-12.1hPa at 20-50℃
• Refractive Index: n20/D 1.481(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 4g/l
• PKA: 1.10±0.10(Predicted)
• Water Solubility: 4 g/L (20 ºC)
• BRN: 879494
• CAS DataBase Reference: 2-Aminobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminobenzotrifluoride(88-17-5)
• EPA Substance Registry System: 2-Aminobenzotrifluoride(88-17-5)

Safety Data

• Hazard Codes: T,Xi,Xn,F
• Statements: 10-23/24/25-33-36/37/38-22-20/21/22
• Safety Statements: 36/37/39-45-37/39-26-16-36
• RIDADR: UN 2942 6.1/PG 3
• WGK Germany: 1
• RTECS: XU9210000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 88-17-5(Hazardous Substances Data)

Usage

General Description

A colorless liquid with a fishlike odor. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Aminobenzotrifluoride is a halogenated amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

InChI:InChI=1/3CHF3O3S.Bi/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3/rC3BiF9O9S3/c5-1(6,7)23(14,15)20-4(21-24(16,17)2(8,9)10)22-25(18,19)3(11,12)13

Synthetic route

N-[2-(trifluoromethyl)phenyl]acetamide (344-62-7) → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With thionyl chloride In methanol at 75℃; for 3h;	94%

(trifluoromethyl)trimethylsilane (81290-20-2) + aniline (62-53-3) → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With 1-acetoxy-1,2-benziodoxol-3-one; potassium acetate In acetonitrile at 80℃; for 13h; Reagent/catalyst; Solvent; Temperature; Time;	89%

2-nitrobenzotrifluoride (384-22-5) → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; sodium trimethylsilanethiolate at 185℃; for 24h;	87%
With sodium hydrogensulfide; sodium hydrogencarbonate In methanol; water for 0.5h; Heating;	68%
In water at 31 - 35℃; for 48h; reduction with baker's yeast (Saccharomyces cerevisiae);	66%

N-(2-(trifluoromethyl)phenyl)picolinamide → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With hydrogenchloride In ethanol	85%
With hydrogenchloride In ethanol at 100℃; for 12h;	1.13 g
With hydrogenchloride In ethanol Reflux;

(trifluoromethyl)trimethylsilane (81290-20-2) + 2-bromoaniline (615-36-1) → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; sodium dodecyl-sulfate; cesium fluoride In toluene at 110℃; for 12h; Inert atmosphere;	70%

Togni's reagent II (887144-94-7) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With potassium carbonate In acetonitrile at 75℃; for 6h; Schlenk technique; Inert atmosphere;	A 20% B 66%
With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2h; Reagent/catalyst; Solvent; Temperature; Overall yield = 89 %;	A 20% B 61%
With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;	A 20% B 49%

iodotrifluoromethane (2314-97-8) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;	A 34% B 54%
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 40 - 50℃; for 0.333333h;	A 7.2 %Spectr. B 8.5 %Spectr.
With dihydrogen peroxide; iron(II) sulfate In water; dimethyl sulfoxide	A 13 %Spectr. B 22 %Spectr.

1-azido-2-(trifluoromethyl)benzene (1548-68-1) → 2-methoxy-3-trifluoromethyl-3H-azepine (90701-87-4) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In tetrahydrofuran; methanol for 15h; Irradiation;	A 49% B 5%

2,3,7,8-tetrafluoro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere;	A 23% B 44%

4-chlorobenzotrifluoride (98-56-6) + aniline (62-53-3) → 3-trifluoromethylaniline (98-16-8) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With 2,3,7,8-tetrafluoro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate In N,N-dimethyl-formamide at 30℃; for 3h; Reagent/catalyst; Inert atmosphere;	A 23% B 44%

3,7-dinitro-Se-(trifluoromethyl)dibenzoselenophenium triflate (129922-39-0) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide for 0.5h; Ambient temperature; Title compound not separated from byproducts;	A 16 % Spectr. B 39%
In N,N-dimethyl-formamide for 0.5h; Ambient temperature; Title compound not separated from byproducts;	A 16 % Spectr. B 39 % Spectr.

Umemoto's reagent (129946-88-9) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 5h; Title compound not separated from byproducts;	A 15% B 37%
In N,N-dimethyl-formamide at 80℃; for 7h;	A 18% B 39 % Spectr.
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere;	A 2% B 5%

aniline (62-53-3) + S-(Trifluoromethyl)-7-nitrodibenzothiophenium-3-sulfonate (160656-66-6) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.5h;	A 18 % Spectr. B 37%
In N,N-dimethyl-formamide at 80℃; for 0.5h;	A 18% B 37 % Spectr.
In N,N-dimethyl-formamide at 80℃; for 0.5h; Product distribution; other temperature;

2,6-difluoro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere;	A 17% B 37%

Bromotrifluoromethane (75-63-8) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With α-picoline; sodium metabisulfite; sulfur dioxide; zinc In N,N-dimethyl-formamide at 20℃; under 2250.2 - 3750.3 Torr; for 2h; Product distribution; other alkylating reagents, other method, other pressure, temp.; various substrates;	A 20% B 36%
With α-picoline; sodium metabisulfite; sulfur dioxide; zinc In N,N-dimethyl-formamide at 20℃; under 2250.2 - 3750.3 Torr; for 2h; also with NaS2O4;	A 20% B 36%
With sulfur dioxide; zinc In N,N-dimethyl-formamide under 2250.2 - 3750.3 Torr; for 2h; Ambient temperature;	A 20% B 36%

Bromotrifluoromethane (75-63-8) + 2-Chloroaniline (95-51-2) → 2-chloro-6-(trifluoromethyl)benzenamine (433-94-3) + 2-chloro-4-(trifluoromethyl)aniline (39885-50-2) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With α-picoline; sodium metabisulfite; sulfur dioxide; zinc In N,N-dimethyl-formamide at 50℃; under 2250.2 - 3750.3 Torr; for 4h;	A 21% B 21% C 14%

2,8-difluoro-5-(trifluoromethyl)-5Hdibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere;	A 6% B 14%

2-nitrobenzotrifluoride (384-22-5) → 4-fluoro-2-(trifluoromethyl)aniline (393-39-5) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With bismuth; hydrogen fluoride In dichloromethane Yields of byproduct given;	A 12% B n/a

2-(trifluoromethyl)benzamide (360-64-5) → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With sodium hypobromide

N-((2-trifluoromethyl)benzene)phthalimide (314-11-4) → 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With steam; hydrazine hydrate

2-(2'-trifluoromethylphenyl)azo-4-phenyl-1,3,4-thiadiazol-5-one (77811-21-3) → 1-phenyl-3-thiosemicarbazide (645-48-7) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
With sodium hydroxide; zinc In methanol Heating;

Se-(trifluoromethyl)dibenzoselenophenium triflate (129922-33-4) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide for 20h; Ambient temperature;	A 4 % Spectr. B 7 % Spectr.
In N,N-dimethyl-formamide for 20h; Ambient temperature; Title compound not separated from byproducts;	A 4 % Spectr. B 7 % Spectr.

3-nitro-S-(trifluoromethyl)dibenzothiophenium triflate (129922-35-6) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide for 0.5h; Ambient temperature; Title compound not separated from byproducts;	A 11 % Spectr. B 18 % Spectr.

S-(trifluoromethyl)-3,7-dinitrodibenzothiophenium trifluoromethanesulfonate (129922-37-8) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Ambient temperature; Title compound not separated from byproducts;	A 26 % Spectr. B 57 % Spectr.

bis(trifluoromethyl)tellurium (55642-42-7) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 3-trifluoromethylaniline (98-16-8) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 60h; Title compound not separated from byproducts;	A 24 % Spectr. B 21 % Spectr. C 21 % Spectr.

aniline (62-53-3) + 5-(trifluoromethyl)-5H-dibenzo[b,d]thiophenium-3-sulfonate (160656-62-2) → 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 7h;	A 18 % Spectr. B 36 % Spectr.
In N,N-dimethyl-formamide at 80℃; for 7h; Product distribution; other time;

Umemoto's reagent (129946-88-9) + aniline (62-53-3) → dibenzothiophene (132-65-0) + 4-trifluoromethylphenylamine (455-14-1) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In d7-N,N-dimethylformamide at 62℃; Kinetics; Thermodynamic data; other temperatures and solvents; ΔH(excit.), ΔS(excit.), ΔG(excit.);

S-(trifluoromethyl)-3,7-dinitrodibenzothiophenium trifluoromethanesulfonate (129922-37-8) + aniline (62-53-3) → 4-trifluoromethylphenylamine (455-14-1) + 3,7-dinitro-dibenzothiophene (59005-75-3) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In d7-N,N-dimethylformamide at -10℃; Kinetics; Thermodynamic data; other temperatures and solvents; ΔH(excit.), ΔS(excit.), ΔG(excit.);

aniline (62-53-3) + trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt → 4-trifluoromethylphenylamine (455-14-1) + diphenyl sulfide (139-66-2) + 2-(trifluoromethyl)benzenamine (88-17-5)

Conditions	Yield
In d7-N,N-dimethylformamide at 81.4℃; Kinetics; Thermodynamic data; other temperatures and solvents; ΔH(excit.), ΔS(excit.), ΔG(excit.);

(cyclopent-2-eneyl)acetic acid (13668-61-6) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2-cyclopent-2-enyl-N-(2-trifluoromethyl-phenyl)-acetamide

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	100%

thiophosgene (463-71-8) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2-(trifluoromethyl)phenyl isothiocyanate (1743-86-8)

Conditions	Yield
In water at 20℃; for 12h;	100%
With sodium hydrogencarbonate In water at 0 - 20℃; for 24h; Inert atmosphere;	95%
With triethylamine In dichloromethane at 20℃; for 1h;

2-thienylacetic acid chloride (39098-97-0) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2-(thiophen-2-yl)-N-(2-(trifluoromethyl)phenyl)acetamide

Conditions	Yield
In tetrahydrofuran at 20℃;	100%

cis-1,2-diphenyloxirane (1689-71-0) + 2-(trifluoromethyl)benzenamine (88-17-5) → C21H18F3NO (1215118-01-6)

Conditions	Yield
With 2C12H25O3S(1-)*Zn(2+); (meso)-1,1'-([2,2'-bipyridine]-6,6'-diyl)bis(2,2-dimethylpropan-1-ol) In water at 20℃; for 22h; enantioselective reaction;	100%

Trichloroacetyl chloride (76-02-8) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2,2,2-trichloro-N-(2-(trifluoromethyl)phenyl)acetamide (349416-85-9)

Conditions	Yield
In 1,4-dioxane for 0.5h; Cooling with ice;	100%
With potassium carbonate In dichloromethane at 20℃; Inert atmosphere;	93%

(R)-N-(1-(3-bromophenyl)ethyl)-3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide (1429217-23-1) + 2-(trifluoromethyl)benzenamine (88-17-5) → (R)-3-methoxy-1-methyl-2-oxo-N-(1-(3-(2-(trifluoromethyl)phenylamino)phenyl)ethyl)-1,2-dihydropyridine-4-carboxamide (1429217-51-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; Inert atmosphere;	100%

pivaloyl chloride (3282-30-2) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-<2-(trifluromethyl)phenyl>-2,2-dimethylpropanamide (125686-52-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	100%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;
With sodium hydrogencarbonate In dichloromethane at 20℃;

3-Bromopropionyl chloride (15486-96-1) + 2-(trifluoromethyl)benzenamine (88-17-5) → 3-bromo-propionic acid-(2-trifluoromethyl-anilide) (3945-39-9)

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	100%
With potassium carbonate

Benzoyl isothiocyanate (532-55-8) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-((2-(trifluoromethyl)phenyl)carbamothioyl)benzamide (63494-72-4)

Conditions	Yield
In acetone for 1.5h; Reflux;	99%
In benzene	86%
In tetrahydrofuran at 60 - 65℃; for 0.166667h; Microwave irradiation;	80%

chloro-diphenylphosphine (1079-66-9) + 2-(trifluoromethyl)benzenamine (88-17-5) → C6H4(o-CF3)NP(C6H5)2P(C6H5)2 (648930-41-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	99%

formaldehyd (50-00-0) + 2-(trifluoromethyl)benzenamine (88-17-5) → 1,3,5-tris(2-(trifluoromethyl)phenyl)-1,3,5-triazinane

Conditions	Yield
In water for 0.0416667h; microwave irradiation;	99%
In water at 20℃; for 0.416667h; Ionic liquid; Green chemistry;	90%

ethyl 2-benzoyl-3-ethoxyacrylate (39973-76-7) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2-benzoyl-3-(2-trifluoromethylphenylamino)acrylic acid ethyl ester (854777-97-2)

Conditions	Yield
In toluene at 150℃; for 1h; Microwave irradiation;	99%
In toluene for 18h; Heating;	82%

2-(trifluoromethyl)benzenamine (88-17-5) → 4-bromo-2-trifluoromethyl-aniline (445-02-3)

Conditions	Yield
With iron(III) chloride; N-Bromosuccinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In toluene at 40℃; regioselective reaction;	99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;	93%
With 1-hexyl-3-methyl-1-imidazolium bromide; copper(ll) bromide for 1h; regioselective reaction;	92%

benzophenone (119-61-9) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-(Diphenylmethylene)-2-(trifluoromethyl)aniline

Conditions	Yield
With tetraethoxy orthosilicate; sulfuric acid at 160℃; for 16h;	98%

pyridine-2-carbaldehyde (1121-60-4) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-(2-pyridylmethylidene)-2-trifluoromethylaniline (386713-04-8)

Conditions	Yield
With 4 A molecular sieve In benzene at 80℃; for 8h;	98%
In toluene for 24h; Reflux;	94%
With toluene-4-sulfonic acid In toluene at 70℃; for 48h; Molecular sieve;	91.9%

3-pyridinecarboxaldehyde (500-22-1) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-(3-pyridylmethylidene)-2-trifluoromethylaniline

Conditions	Yield
With 4 A molecular sieve In benzene at 80℃; for 8h;	98%

formaldehyd (50-00-0) + 2-(trifluoromethyl)benzenamine (88-17-5) + monophenylthiourea (103-85-5) → 1-phenyl-5-(2-trifluoromethyl-phenyl)-[1,3,5]triazinane-2-thione (701277-33-0)

Conditions	Yield
In water for 0.0138889h; microwave irradiation;	98%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + 2-(trifluoromethyl)benzenamine (88-17-5) → tert-butyl-(2-trifluoromethyl-phenyl)-amine (864365-12-8)

Conditions	Yield
With boron trifluoride diethyl etherate In cyclohexane at 20℃;	98%

1-Phenylprop-1-yne (673-32-5) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-cinnamyl-2-(trifluoromethyl)aniline

Conditions	Yield
With palladium diacetate; benzoic acid In toluene at 110℃; for 5h;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; benzoic acid In toluene at 110℃; for 1h; Inert atmosphere; chemoselective reaction;	98%

trifluoroacetic acid (76-05-1) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (2368-64-1)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 15.5h; Inert atmosphere;	98%

diisopropyl-carbodiimide (693-13-0) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2-(trifluoromethylphenyl)-1,3-diisopropylguanidine

Conditions	Yield
With diethylzinc In hexane; toluene at 50℃; for 2h; Schlenk technique; Inert atmosphere;	98%

chloral (75-87-6) + 2-(trifluoromethyl)benzenamine (88-17-5) → (E)-2-(hydroxyimino)-N-(2-(trifluoromethyl)phenyl)acetamide (444-93-9)

Conditions	Yield
With hydroxyammonium sulfate; sodium sulfate In ethanol at 60 - 80℃; for 6h;	97%

1-Adamantanecarbonyl chloride (2094-72-6) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-[2-(trifluoromethyl)phenyl]adamantane-1-carboxamide

Conditions	Yield
With triethylamine In acetone at 90℃; for 3h; Inert atmosphere;	97%

acetylacetone (123-54-6) + 2-(trifluoromethyl)benzenamine (88-17-5) → C12H11F3N2O2

Conditions	Yield
Stage #1: 2-(trifluoromethyl)benzenamine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 0 - 20℃; for 4h;	97%

benzenesulfonyl chloride (98-09-9) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-(2-(trifluoromethyl)phenyl)benzenesulfonamide (86802-68-8)

Conditions	Yield
With pyridine In acetonitrile at 35 - 55℃; for 6.5h; Inert atmosphere; Large scale;	96.8%
With pyridine at 85℃; for 8h;	88%
With pyridine at 146℃; for 4h;	43%

acetic anhydride (108-24-7) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-[2-(trifluoromethyl)phenyl]acetamide (344-62-7)

Conditions	Yield
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In neat (no solvent) at 50℃; for 0.5h; Green chemistry;	96%
at 80℃; for 5h; Large scale;	95%
Stage #1: acetic anhydride; 2-(trifluoromethyl)benzenamine at 20℃; for 1h; Stage #2: With water; sodium hydrogencarbonate	92%

formaldehyd (50-00-0) + 2-trifluoromethylphenyl thiourea (1736-71-6) + 2-(trifluoromethyl)benzenamine (88-17-5) → 1-(2-trifluoromethylphenyl)-5-(2-trifluoromethylphenyl)-2-thioxo hexahydro-1,3,5-triazine (701277-32-9)

Conditions	Yield
In water for 0.0125h; microwave irradiation;	96%

2-(trifluoromethyl)benzenamine (88-17-5) → 4-amino-3-(trifluoromethyl)phenyl thiocyanate (68672-37-7)

Conditions	Yield
With bromine In methanol; dichloromethane	96%

4-bromoohenyl methyl sulfone (3466-32-8) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-(4-(methylsulfonyl)phenyl)-2-(trifluoromethyl)aniline

Conditions	Yield
With sodium phenoxide; C47H70BrO4PPdSi In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube;	96%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 80℃; for 8h; Reagent/catalyst; Inert atmosphere;	83%

1-(4-fluorophenyl)ethanone (403-42-9) + 2-(trifluoromethyl)benzenamine (88-17-5) → N-<1-(4-fluorophenyl)ethylidene>-2-(trifluoromethyl)aniline (133671-30-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 10h; Heating;	95%

Upstream product

• 1548-68-1 1-azido-2-(trifluoromethyl)benzene 
• 129946-88-9 Umemoto's reagent 
• 62-53-3 aniline 
• 129922-33-4 Se-(trifluoromethyl)dibenzoselenophenium triflate 
• 129922-35-6 3-nitro-S-(trifluoromethyl)dibenzothiophenium triflate 
• 129922-37-8 S-(trifluoromethyl)-3,7-dinitrodibenzothiophenium trifluoromethanesulfonate 
• 129922-39-0 3,7-dinitro-Se-(trifluoromethyl)dibenzoselenophenium triflate 
• 75-63-8 Bromotrifluoromethane 
• 95-51-2 o-chloroaniline 
• 384-22-5 2-nitrobenzotrifluoride 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 7647-01-0 hydrogenchloride 
• 1891-90-3 p-trifluoromethylbenzamide 

Downstream Products

• 25434-13-3 N,N-bis-(4-chloro-phenyl)-urea 
• 340-66-9 4,5,6,7-tetrachloro-2-(2-trifluoromethyl-phenyl)-isoindoline-1,3-dione 
• 393-34-0 3-oxo-3-phenyl-propionic acid-(2-trifluoromethyl-anilide) 
• 344-61-6 (E)-1-phenyl-N-(2-(trifluoromethyl)phenyl)methanimine 
• 133671-37-1 N-<1-(3-pyridyl)ethylidene>-2-(trifluoromethyl)aniline 
• 133671-39-3 N-<1-(2-furanyl)ethylidene>-2-(trifluoromethyl)aniline 
• 126404-37-3 2-methylene-4-oxo-4-((2-(trifluoromethyl)phenyl)amino)-butanoic acid 
• 419534-37-5 2-cyano-N-[2-(trifluoromethyl)phenyl]acetamide 
• 344-62-7 N-[2-(trifluoromethyl)phenyl]acetamide 
• 75040-61-8 2-trifluoromethyl-N-(1-phenylethylidene)benzenamine 
• 128924-94-7 N-(1-phenylethylidene)-2-(trifluoromethyl)aniline 
• 29483-73-6 2-(2-aminophenyl)benzthiazole 
• 137434-30-1 (E)-N-(1-phenylpropylidene)-2-(trifluoromethyl)aniline 
• 86802-68-8 N-(2-(trifluoromethyl)phenyl)benzenesulfonamide 

Relevant articles and documents

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

o-aminotrifluorotoluene synthesis method

The invention discloses an o-aminotrifluorotoluene synthesis method, wherein trifluorotoluene is used as a raw material, and a target compound is obtained through two-step reaction of nitration and reduction. Compared with the method in the prior art, the method of the invention has the following characteristics that trifluorotoluene is used as the raw material, so that the source is wide, and thepreparation is convenient; the nitration reaction is carried out at a normal pressure and a low temperature, so that the corrosion of the material to the pipeline and the equipment is small, and thenitration reaction is safe and reliable to the environment and operators; and the cheap nickel catalyst is used for replacing the common noble metal catalysts such as palladium, platinum and the like,so that the production cost is reduced, the methanol as the solvent is convenient to recover and can be recycled, and the emission of organic matters in the production process is reduced.

Visible-light-induced Pd-catalyzed: Ortho -trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst

A visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na was developed. The reaction proceeded smoothly at room temperature in air without any external photocatalyst or additive, providing the desired products in moderate to good yields with good functional group tolerance and regioselectivity.