Product Name

  • Name

    2-(Trifluoromethoxy)aniline

  • EINECS 216-257-9
  • CAS No. 1535-75-7
  • Article Data5
  • CAS DataBase
  • Density 1.301 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H6F3NO
  • Boiling Point 170.2 °C at 760 mmHg
  • Molecular Weight 177.126
  • Flash Point 56.7 °C
  • Transport Information UN 1993
  • Appearance clear, very faintly yellow liquid
  • Safety 36/37/39-26-45-16
  • Risk Codes 36/37/38-20/21/22-10
  • Molecular Structure Molecular Structure of 1535-75-7 (2-(Trifluoromethoxy)aniline)
  • Hazard Symbols HarmfulXn,ToxicT,IrritantXi
  • Synonyms o-Anisidine,a,a,a-trifluoro- (6CI,7CI,8CI);2-(Trifluoromethoxy)benzenamine;2-Trifluoromethoxyaniline;o-(Trifluoromethoxy)aniline;
  • PSA 35.25000
  • LogP 2.74860

Synthetic route

1-bromo-2-(trifluoromethoxy)benzene
64115-88-4

1-bromo-2-(trifluoromethoxy)benzene

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

Conditions
ConditionsYield
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h;82%
1-chloro-4-(trifluoromethoxy)benzene
461-81-4

1-chloro-4-(trifluoromethoxy)benzene

A

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

B

m-trifluoromethoxyaniline
1535-73-5

m-trifluoromethoxyaniline

Conditions
ConditionsYield
Stage #1: 1-chloro-4-(trifluoromethoxy)benzene With sulfuric acid; nitric acid at 0 - 45℃;
Stage #2: With palladium on activated charcoal; hydrogen; triethylamine In methanol at 80℃; under 15001.5 Torr; Temperature; Pressure; Autoclave; Overall yield = 98 percent; Overall yield = 177.12 g;
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

2-(trifluoromethoxy)benzenesulfonyl chloride
103008-51-1

2-(trifluoromethoxy)benzenesulfonyl chloride

2-trifluoromethoxy-benzenesulphonic acid amide
37526-59-3

2-trifluoromethoxy-benzenesulphonic acid amide

Conditions
ConditionsYield
99.4%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

tert-butyl N-[2-(trifluoromethoxy)phenyl]carbamate
561304-39-0

tert-butyl N-[2-(trifluoromethoxy)phenyl]carbamate

Conditions
ConditionsYield
In toluene at 100℃; for 2h;98%
In toluene Heating;76%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

ethyl acetoacetate
141-97-9

ethyl acetoacetate

3-oxo-2-(2-(2-(trifluoromethoxy)phenyl)hydrazono)butanoic acid ethyl ester
1620683-57-9

3-oxo-2-(2-(2-(trifluoromethoxy)phenyl)hydrazono)butanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-trifluoromethoxy aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: ethyl acetoacetate With sodium acetate In ethanol; water at 0℃;		92.3%
Stage #1: 2-trifluoromethoxy aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.0833333h;
Stage #2: ethyl acetoacetate With ammonium acetate In ethanol; water
Stage #1: 2-trifluoromethoxy aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.0833333h;
Stage #2: ethyl acetoacetate With ammonium acetate In ethanol; water at 0℃; for 0.5h;
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

t-butyl 2-diazopropanoate
805237-13-2

t-butyl 2-diazopropanoate

(-)-tert-butyl 2-((2-(trifluoromethoxy)phenyl)amino)propanoate

(-)-tert-butyl 2-((2-(trifluoromethoxy)phenyl)amino)propanoate

Conditions
ConditionsYield
With C32H30N4O4; copper(l) chloride In dichloromethane at 0℃; for 18h; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;92%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

sodium formate
141-53-7

sodium formate

N-(2-(trifluoromethoxy)phenyl)formamide

N-(2-(trifluoromethoxy)phenyl)formamide

Conditions
ConditionsYield
With formic acid for 12h; Reflux;90.56%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

ethyl 2-chloro-3-oxo-butyrate
609-15-4

ethyl 2-chloro-3-oxo-butyrate

ethyl 2-chloro-2-(2-(2-(trifluoromethoxy)phenyl)hydrazono)acetate

ethyl 2-chloro-2-(2-(2-(trifluoromethoxy)phenyl)hydrazono)acetate

Conditions
ConditionsYield
Stage #1: 2-trifluoromethoxy aniline With hydrogenchloride; sodium nitrite In ethanol; water at 0 - 5℃; for 0.5h;
Stage #2: ethyl 2-chloro-3-oxo-butyrate With sodium acetate In ethanol; water at 0 - 25℃;		90%
tin(II)chloride dihydrate

tin(II)chloride dihydrate

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

[2-(trifluoromethoxy)phenyl]hydrazine hydrochloride

[2-(trifluoromethoxy)phenyl]hydrazine hydrochloride

Conditions
ConditionsYield
With sodium nitrite In hydrogenchloride; water88%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

2-nitro-N-(2-(trifluoromethoxy)phenyl)benzamide
939920-68-0

2-nitro-N-(2-(trifluoromethoxy)phenyl)benzamide

Conditions
ConditionsYield
Stage #1: ortho-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide; benzene Reflux;
Stage #2: 2-trifluoromethoxy aniline With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;		88%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

cyanoacetic acid
372-09-8

cyanoacetic acid

2-cyano-N-(2-trifluoromethoxyphenyl)acetamide

2-cyano-N-(2-trifluoromethoxyphenyl)acetamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; Inert atmosphere;87%
3-bromo-3-methyl-2-indolinone
2406-05-5

3-bromo-3-methyl-2-indolinone

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

(R)-3-methyl-3-((2-(trifluoromethoxy)phenyl)amino)indolin-2-one

(R)-3-methyl-3-((2-(trifluoromethoxy)phenyl)amino)indolin-2-one

Conditions
ConditionsYield
Stage #1: 3-bromo-3-methyl-2-indolinone With nickel(II) tetrafluoroborate hexahydrate; C42H66N4O8 In ethyl acetate at 35℃; for 0.583333h;
Stage #2: With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667h;
Stage #3: 2-trifluoromethoxy aniline In ethyl acetate at 0℃; for 24h; enantioselective reaction;		86%
chloral hydrate
302-17-0

chloral hydrate

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

2-hydroxyimino-N-(2-trifluoromethoxy-phenyl)-acetamide

2-hydroxyimino-N-(2-trifluoromethoxy-phenyl)-acetamide

Conditions
ConditionsYield
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate at 55℃; Sandmeyer reaction;85%
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate at 55℃; Sandmeyer reaction;85%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

C20H21NO4

C20H21NO4

C27H25F3N2O4

C27H25F3N2O4

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;85%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

C20H21NO4

C20H21NO4

C27H25F3N2O4

C27H25F3N2O4

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Inert atmosphere;85%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

tetra(n-butyl)ammonium hydrogensulfate
32503-27-8

tetra(n-butyl)ammonium hydrogensulfate

tetrabutylammonium (2‐(trifluoromethoxy)phenyl)sulfamate

tetrabutylammonium (2‐(trifluoromethoxy)phenyl)sulfamate

Conditions
ConditionsYield
Stage #1: 2-trifluoromethoxy aniline With chlorosulfonic acid; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With sodium hydroxide In dichloromethane; water
Stage #3: tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water		85%
4-bromoohenyl methyl sulfone
3466-32-8

4-bromoohenyl methyl sulfone

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

N-(4-(methylsulfonyl)phenyl)-2-(trifluoromethoxy)aniline

N-(4-(methylsulfonyl)phenyl)-2-(trifluoromethoxy)aniline

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 80℃; for 8h; Reagent/catalyst; Inert atmosphere;85%
(4-bromo-3-methylphenyl)(morpholino)methanone
149105-06-6

(4-bromo-3-methylphenyl)(morpholino)methanone

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

C19H19F3N2O3

C19H19F3N2O3

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C37H43N2O4P In 1,4-dioxane at 90℃; for 18h;82%
Octanethiol
111-88-6

Octanethiol

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

2-(n-octylthio)-1-trifluoromethoxybenzene

2-(n-octylthio)-1-trifluoromethoxybenzene

Conditions
ConditionsYield
With tert.-butylnitrite; C29H23N6Ru2(2+)*2Cl(1-)*6H2O; toluene-4-sulfonic acid In acetonitrile at 20℃; for 5h; Irradiation;81%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

C10H6F3NO3

C10H6F3NO3

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; 2-trifluoromethoxy aniline Heating;
Stage #2: With Eaton’s reagent Heating;		81%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

p-cyanophenyl isocyanate
40465-45-0

p-cyanophenyl isocyanate

1-(4-cyanophenyl)-3-(2-trifluoromethoxyphenyl)urea
1416274-64-0

1-(4-cyanophenyl)-3-(2-trifluoromethoxyphenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;80.4%
2-methylquinoline
91-63-4

2-methylquinoline

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

(4-amino-3-(trifluoromethoxy)phenyl)(quinolin-2-yl)methanone

(4-amino-3-(trifluoromethoxy)phenyl)(quinolin-2-yl)methanone

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide; salicylic acid at 90℃; under 760.051 Torr; for 16h; Schlenk technique; regioselective reaction;80%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

2-phenyl-8-(trifluoromethoxy)quinoline

2-phenyl-8-(trifluoromethoxy)quinoline

Conditions
ConditionsYield
With oxygen; palladium diacetate In dimethyl sulfoxide at 130℃; under 760.051 Torr; for 12h;78%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

1-(2,4-dinitrophenyl)-1′-(2-isopropylphenyl)-4,4′-bipyridinium bis(tetrafluoroborate)

1-(2,4-dinitrophenyl)-1′-(2-isopropylphenyl)-4,4′-bipyridinium bis(tetrafluoroborate)

1-(2-trifluoromethoxyphenyl)-1′-(2-isopropylphenyl)-4,4′-bipyridinium bis(tetrafluoroborate)

1-(2-trifluoromethoxyphenyl)-1′-(2-isopropylphenyl)-4,4′-bipyridinium bis(tetrafluoroborate)

Conditions
ConditionsYield
In methanol for 48h; Reflux;77%
N-vinyl-2-oxazolidone
4271-26-5

N-vinyl-2-oxazolidone

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-(2-(2-oxooxazolidin-3-yl)-2-((2-trifluoromethoxyphenyl)amino)ethyl)malonate

diethyl 2-(2-(2-oxooxazolidin-3-yl)-2-((2-trifluoromethoxyphenyl)amino)ethyl)malonate

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 3h; Inert atmosphere; Sealed tube; Irradiation;77%
...Expand
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

N-(2-methoxybenzyl)-2-(trifluoromethoxy)aniline

N-(2-methoxybenzyl)-2-(trifluoromethoxy)aniline

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h;75%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

acetophenone
98-86-2

acetophenone

1-(4-amino-3-(trifluoromethoxy)phenyl)-2-phenylethane-1,2-dione

1-(4-amino-3-(trifluoromethoxy)phenyl)-2-phenylethane-1,2-dione

Conditions
ConditionsYield
With copper(l) iodide; boron trifluoride diethyl etherate; oxygen In dimethyl sulfoxide at 105℃; for 14h; regioselective reaction;75%
cycl-isopropylidene cyclopropane-1,1-dicarboxylate
5617-70-9

cycl-isopropylidene cyclopropane-1,1-dicarboxylate

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

2-oxo-1-(2-(trifluoromethoxy)phenyl)pyrrolidine-3-carboxylic acid

2-oxo-1-(2-(trifluoromethoxy)phenyl)pyrrolidine-3-carboxylic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 30 - 35℃; for 12h;72.3%
(Z)-2,2'-dibromostilbene
56667-12-0, 108474-32-4, 56667-11-9

(Z)-2,2'-dibromostilbene

2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

5-(2-(trifluoromethoxy)phenyl)-5H-dibenzo[b,f]azepine
1414856-44-2

5-(2-(trifluoromethoxy)phenyl)-5H-dibenzo[b,f]azepine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 120℃; for 10h; Schlenk technique; Inert atmosphere;72%
2-trifluoromethoxy aniline
1535-75-7

2-trifluoromethoxy aniline

1,4-dinitro-1H-imidazole
19182-81-1

1,4-dinitro-1H-imidazole

4-nitro-1-{2-(trifluoromethoxy)phenyl}-1H-imidazole
1297344-95-6

4-nitro-1-{2-(trifluoromethoxy)phenyl}-1H-imidazole

Conditions
ConditionsYield
In methanol; water at 20℃; Darkness;71%

2-(Trifluoromethoxy)aniline Chemical Properties

Synonyms: 2-(TRIFLUOROMETHOXY)ANILINE;2-TRIFLUOROMETHOXY-PHENYLAMINE;ALPHA,ALPHA,ALPHA-TRIFLUORO-O-ANISIDINE;O-(TRIFLUOROMETHOXY)ANILINE;TIMTEC-BB SBB006602;2-(Trifluoromethoxy)ANILINE o-(Trifluoromethoxy)ANILINE;O-Aminotrifluorome;2-Aminotrifluoromethoxybenzene
MF: C7H6F3NO
MW: 177.12
EINECS: 216-257-9
BP:  61-63 °C (15 mmHg) 
Density : 1,301 g/cm3
Refractive Index : 1.4614-1.4634 
FP : 54°C
BRN : 2803814
CAS DataBase Reference : 1535-75-7
NIST Chemistry Reference : 1535-75-7
Structural Formula:

2-(Trifluoromethoxy)aniline Toxicity Data With Reference

Hazard Codes : Xn,T,Xi
Risk Statements :
R36/37/38:  Irritating to eyes, respiratory system and skin 
R20/21/22:  Harmful by inhalation, in contact with skin and if swallowed
R10:  Flammable  

2-(Trifluoromethoxy)aniline Safety Profile

Safety Statements :
S36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
S26:  In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice
S45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
S16:  Keep away from sources of ignition - No smoking 
S36:  Wear suitable protective clothing

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