121-01-7

Basic information

• Product Name: 2-Amino-5-nitrobenzotrifluoride
• Synonyms: 2-AMINO-5-NITRO-TRIFLUOROBENZENE;2-AMINO-5-NITROBENZOTRIFLUORIDE;2-TRIFLUOROMETHYL-4-NITROANILINE;A,A,A-TRIFLUORO-4-NITRO-O-TOLUIDINE;5-NITRO-2-AMINOBENZOTRIFLUORIDE;4-NITRO-2-(TRIFLUOROMETHYL)ANILINE;4-NITRO-ALPHA,ALPHA,ALPHA-TRIFLUORO-O-TOLUIDINE;4-Nitro-a,a,a-trifluoro-o-toluidine
• CAS NO: 121-01-7
• Molecular Formula: C₇H₅F₃N₂O₂
• Molecular Weight: 206.12
• EINECS: 204-443-2
• Product Categories: Trifluoromethylbenzene serise;Fluorobenzene;Amines;Phenyls & Phenyl-Het;Miscellaneous;Phenyls & Phenyl-Het;Building Blocks;C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Pyrrolidines
• Mol File: 121-01-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 298 °C at 760 mmHg
• Flash Point: 134 °C
• Appearance: Yellow to brown/Powder
• Density: 1.4711 (estimate)
• Vapor Pressure: 1.01E-05mmHg at 25°C
• Refractive Index: 1.427
• Storage Temp.: Store below +30°C.
• PKA: -1.92±0.36(Predicted)
• BRN: 2121347
• CAS DataBase Reference: 2-Amino-5-nitrobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-nitrobenzotrifluoride(121-01-7)
• EPA Substance Registry System: 2-Amino-5-nitrobenzotrifluoride(121-01-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37-24/25-36
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 121-01-7(Hazardous Substances Data)

Usage

Description

4-Nitro-2-(trifluoromethyl)aniline undergoes diazotization and coupling with:N-hydroxyalkylamino-5-naptholspyrazolones and naptholsulphonic acidsN-(2-cyanoethyl)-N-(hydroxyalkyl)anilines

Chemical Properties

YELLOW TO BROWN POWDER

Uses

4-Nitro-2-(trifluoromethyl)aniline was used in the synthesis of monoazo dyes.

General Description

4-Nitro-2-(trifluoromethyl)aniline undergoes diazotization and coupling with:N-hydroxyalkylamino-5-naptholspyrazolones and naptholsulphonic acidsN-(2-cyanoethyl)-N-(hydroxyalkyl)anilines

InChI:InChI=1/C13H6F8N2O/c14-10(15)12(18,19)13(20,21)11(16,17)6-24-9-2-1-7(4-22)8(3-9)5-23/h1-3,10H,6H2

Synthetic route

3-trifluoromethylnitrobenzene (98-46-4) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
With potassium hydroxide; N,N-tetramethylene-thiocarbamoyl-sulphenamide In ammonia	91%
With sodium ethanolate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In ammonia; N,N-dimethyl-formamide for 0.583333h;	84%

C7H3F3N4O2 (1440512-30-0) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
Stage #1: C7H3F3N4O2 With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; tert-butyl alcohol In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	84%

4-chloro-3-(trifluoromethyl)nitrobenzene (777-37-7) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
With sodium azide; copper(ll) sulfate pentahydrate; sodium carbonate; sodium L-ascorbate; L-proline In water; dimethyl sulfoxide at 70℃; for 24h;	72%
With ammonia at 140℃;
With ammonia; copper(l) chloride at 120℃;
With ammonia

Langlois reagent (2926-29-6) + 4-nitro-aniline (100-01-6) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
With tert.-butylhydroperoxide In dichloromethane; water at 0 - 15℃;	42%

2-(trifluoromethyl)benzenamine (88-17-5) → 4-nitro-2-trifluoromethyl-aniline (121-01-7) + 2-Nitro-6-(trifluoromethyl)aniline (24821-17-8)

Conditions	Yield
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In trifluoroacetic acid for 3h; Ambient temperature;	A 40% B 30%

3-trifluoromethylnitrobenzene (98-46-4) → 4-nitro-2-trifluoromethyl-aniline (121-01-7) + 4-trifluoromethyl-2-nitroaniline (400-98-6)

Conditions	Yield
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;	A 29% B 6%

N-(4-nitro-2-(trifluoromethyl)phenyl)acetamide (395-68-6) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
With sodium hydroxide

3-trifluoromethylnitrobenzene (98-46-4) → 4-nitro-2-trifluoromethyl-aniline (121-01-7) + 2-Nitro-6-(trifluoromethyl)aniline (24821-17-8) + 4-trifluoromethyl-2-nitroaniline (400-98-6)

Conditions	Yield
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With O-Methylhydroxylamin; copper(l) chloride In N,N-dimethyl-formamide at 20℃; for 1h; Product distribution; Further Variations:; also without CuCl; Substitution; Amination;

N-[2-(trifluoromethyl)phenyl]acetamide (344-62-7) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4; HNO3 2: aq.-ethanolic NaOH View Scheme

1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, H2SO4 2: liq. NH3 View Scheme

petroleum + S-diethylthiocarbamoyl-substituted sulfenamide (106860-28-0) + 3-trifluoromethylnitrobenzene (98-46-4) → 4-nitro-2-trifluoromethyl-aniline (121-01-7) + 4-nitro-3-(trifluoromethyl)benzeneamine (393-11-3)

Conditions	Yield
With sodium hydroxide In N-methyl-acetamide; methanol; ammonia; water	A 3.5 g (85%) B n/a

pyridine-2-carboxylic acid (4-nitro-phenyl)amide (61349-99-3) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(I) bromide; dipotassium peroxodisulfate / acetonitrile / 12 h / 50 °C 2: hydrogenchloride / ethanol / 12 h / 100 °C View Scheme

N-(4-nitro-2-(trifluoromethyl)phenyl)picolinamide → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
With hydrogenchloride In ethanol at 100℃; for 12h;

iodotrifluoromethane (2314-97-8) + 4-nitro-aniline (100-01-6) → 4-nitro-2-trifluoromethyl-aniline (121-01-7)

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;	50.2 g

4-nitro-2-trifluoromethyl-aniline (121-01-7) → 2-bromo-4-nitro-6-trifluoromethylaniline (400-66-8)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline With hydrogen bromide at 20 - 70℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water at 60 - 70℃; for 3h;	99.2%
With bromine In acetic acid at 120℃; for 2.5h;	91%
With bromine; acetic acid at 120℃; for 2.5h;	91%
With bromine In acetic acid 1.) 45 deg C, 2.5 h, 2.) reflux, 4.75 h;	81%
With bromine; acetic acid

thiophosgene (463-71-8) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1-isothiocyanato-4-nitro-2-(trifluoromethyl)benzene

Conditions	Yield
With sodium hydrogencarbonate In water; toluene at 0 - 75℃; for 120h; Inert atmosphere;	99%
In toluene at 75℃; for 120h; Inert atmosphere;	99%
In dichloromethane; water at 0 - 20℃; for 24h; Inert atmosphere;

1,5-pentanedioic acid (110-94-1) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1-(4-nitro-2-trifluoromethyl-phenyl)-piperidine-2,6-dione

Conditions	Yield
With PPA at 80℃; for 12h;	98%

4-nitro-2-trifluoromethyl-aniline (121-01-7) → 2-chloro-4-nitro-6-trifluoromethyl-aniline (400-67-9)

Conditions	Yield
With N-chloro-succinimide In acetonitrile at 150℃; for 0.25h; Microwave irradiation;	97%
With N-chloro-succinimide In acetonitrile at 150℃; for 0.166667h; Microwave;	75%
With chlorine; acetic acid

succinic acid (110-15-6) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1-(4-nitro-2-trifluoromethylphenyl)pyrrolidine-2,5-dione

Conditions	Yield
With PPA at 80℃; for 12h;	97%
With PPA at 85℃; for 20h;	97%
With polyphosphoric acid at 80℃; for 12h;	92%

4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1-iodo-4-nitro-2-(trifluoromethyl)benzene (400-75-9)

Conditions	Yield
With sodium iodide; sodium nitrite In sulfuric acid; water	94%
With sulfuric acid; acetic acid; potassium iodide; sodium nitrite
With CuI; sodium nitrite In methanol; ice-water; H2SO4/H2O; water
Stage #1: 4-nitro-2-trifluoromethyl-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium iodide In water at 0 - 20℃;

4-nitro-2-trifluoromethyl-aniline (121-01-7) + Methacryloyl chloride (920-46-7) → N-(4-nitro-2-(trifluoromethyl)phenyl)methacrylamide

Conditions	Yield
In N,N-dimethyl acetamide at 20℃;	94%
In N,N-dimethyl acetamide at 20℃;	94%
In N,N-dimethyl acetamide at 20℃; for 3h; Inert atmosphere;	77%

formaldehyd (50-00-0) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1,3,5-tris(4-nitro-2-(trifluoromethyl)phenyl)-1,3,5-triazinane (1628797-85-2)

Conditions	Yield
In water at 20℃; for 0.416667h; Ionic liquid; Green chemistry;	91%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + 6-(4-fluorophenyl)-2-pyridinecarboxaldehyde (834884-77-4) → 2-[(4-nitro-2-trifluoromethylphenylimino)methyl]-6-[4-fluorophenyl]pyridine

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 60℃; for 65h; Molecular sieve;	91%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + methyl 4-formylbenzoate (1571-08-0) → methyl 4-{[4-nitro-2-(trifluoromethyl)phenylimino]methyl}benzoate (384837-22-3)

Conditions	Yield
In ethanol Reflux;	90%

di-tert-butyl dicarbonate (24424-99-5) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → tert-butyl N-tert-butoxycarbonyl-N-[4-nitro-2-(trifluoromethyl)phenyl]carbamate (1089725-58-5)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran for 5h; Heating / reflux;	88%
With dmap In tetrahydrofuran at 20℃;
With dmap In 1,4-dioxane at 20 - 110℃; for 2h;	5.3 g

4-nitro-2-trifluoromethyl-aniline (121-01-7) + allyl bromide (106-95-6) → 4-nitro-1-(prop-2-en-1-yl)-2-(trifluoromethyl)benzene

Conditions	Yield
With tert.-butylnitrite In acetonitrile at 18 - 26℃; for 1.33h;	85%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + cyclohexanecarbaldehyde (2043-61-0) → N-(4-nitro-2-(trifluoromethyl)phenyl)cyclohexanecarboxamide (1426575-31-6)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline With tert.-butylnitrite; trimethylsilylazide In tetrahydrofuran at 0℃; Stage #2: cyclohexanecarbaldehyde With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; sodium t-butanolate In tetrahydrofuran at -25℃;	83%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + benzaldehyde (100-52-7) → N-(4-nitro-2-(trifluoromethyl)phenyl)benzamide (121408-37-5)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline With tert.-butylnitrite; trimethylsilylazide In tetrahydrofuran at 0℃; Stage #2: benzaldehyde With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; sodium t-butanolate In tetrahydrofuran at -25℃;	77%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → N-[4-(pyridin-3-yl)pyrimidin-2-yl]cyanamide (1144477-16-6)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline With nitric acid In ethanol at 0℃; Stage #2: With CYANAMID In ethanol; water Reflux; Stage #3: 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one In isopropyl alcohol Reflux;	75%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + toluene-4-sulfonic acid (104-15-4) → 4-nitro-2-(trifluoromethyl)benzenediazonium tosylate

Conditions	Yield
With tert.-butylnitrite In ethyl acetate at 20℃; for 0.25h;	74%

di-tert-butyl dicarbonate (24424-99-5) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → N4-(tert-butoxycarbonyl)-2-trifluoromethyl-1,4-phenylenediamine (1016506-18-5)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline With palladium 10% on activated carbon; hydrogen In methanol under 2068.65 Torr; for 7h; Stage #2: di-tert-butyl dicarbonate In methanol Reflux;	72.9%

4-nitro-2-trifluoromethyl-aniline (121-01-7) → 4-nitro-2-(trifluoromethyl)benzenesulfonyl chloride (444-46-2)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline With hydrogenchloride; acetic acid; sodium nitrite In water at 15℃; for 3h; Inert atmosphere; Stage #2: With sulfur dioxide; copper dichloride In water at 5 - 20℃;	71%
With hydrogenchloride; sulfur dioxide; acetic acid; copper dichloride; sodium nitrite In water at 5 - 20℃;	71%
With hydrogenchloride; sulfur dioxide; copper(l) chloride; sodium nitrite 1.) glacial AcOH, from -10 deg C to -5 deg C, 15 min, 2.) glacial AcOH, from 5 deg C to RT, 1.5 h; Yield given. Multistep reaction;

4-nitro-2-trifluoromethyl-aniline (121-01-7) + 3-tert-Butyl-1-methyl-1H-pyrazole-5-carbonyl chloride (160842-62-6) → 5-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid (4-nitro-2-trifluoromethyl-phenyl)-amide

Conditions	Yield
With pyridine In dichloromethane at 80℃;	68%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + maleic acid → 1-(4-nitro-2-trifluoromethyl-phenyl)-pyrrole-2,5-dione

Conditions	Yield
With PPA at 80℃; for 12h;	68%

4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triazene (1243357-92-7)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 48h;	68%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + 3,4-diethoxybenzoic acid (5409-31-4) → 3,4-diethoxy-N-(4-nitro-2-(trifluoromethyl)phenyl)benzamide

Conditions	Yield
With phosphorus trichloride In toluene Reflux;	64%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 5-chloro-2-hydroxy-N-(4-nitro-2-(trifluoromethyl)phenyl) benzamide

Conditions	Yield
With phosphorus trichloride In toluene Reflux;	63%

4-nitro-2-trifluoromethyl-aniline (121-01-7) + Cinnamic acid (621-82-9) → (2E)-N-[4-nitro-2-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide

Conditions	Yield
With phosphorus trichloride In chlorobenzene at 130℃; for 0.5h; Microwave irradiation;	61%

methyl 3-bromobenzoate (618-89-3) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 3-(4-nitro-2-(trifluoromethyl)phenylamino)benzoic acid methyl ester (1359968-17-4)

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 20 - 120℃; Buchwald-Hartwig reaction; Inert atmosphere;	56%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 2-chloro-3-(4-nitro-2-trifluoromethyl-phenylamino)-[1,4]naphthoquinone + 2,3-bis-(4-nitro-2-trifluoromethyl-phenylamino)-[1,4]naphthoquinone

Conditions	Yield
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 80℃; for 12h;	A 55% B n/a

4-nitro-2-trifluoromethyl-aniline (121-01-7) + methyl 4-formylbenzoate (1571-08-0) → methyl 4-{[4-nitro-2-(trifluoromethyl)phenylamino]methyl}benzoate (1427066-93-0)

Conditions	Yield
Stage #1: 4-nitro-2-trifluoromethyl-aniline; methyl 4-formylbenzoate In benzene at 60℃; Stage #2: With sodium tetrahydroborate; acetic acid In benzene at 0 - 50℃;	55%

Upstream product

• 88-17-5 2-(trifluoromethyl)benzenamine 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 106860-28-0 S-diethylthiocarbamoyl-substituted sulfenamide 
• 2314-97-8 iodotrifluoromethane 
• 100-01-6 4-nitro-aniline 
• 61349-99-3 pyridine-2-carboxylic acid (4-nitro-phenyl)amide 
• 2926-29-6 Langlois reagent 
• 1440512-30-0 C₇H₃F₃N₄O₂ 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 344-62-7 N-[2-(trifluoromethyl)phenyl]acetamide 
• 395-68-6 N-(4-nitro-2-(trifluoromethyl)phenyl)acetamide 
• 777-37-7 4-chloro-3-(trifluoromethyl)nitrobenzene 

Downstream Products

• 17128-22-2 4-Dimethylamino-4'-nitro-2'-trifluormethyl-azobenzol 
• 444-46-2 4-nitro-2-(trifluoromethyl)benzenesulfonyl chloride 
• 86785-34-4 N-(2-trifluoromethyl-4-nitrophenyl)benzenesulfonamide 
• 364-13-6 2-(trifluoromethyl)-1,4-phenylenediamine 
• 1089725-58-5 tert-butyl N-tert-butoxycarbonyl-N-[4-nitro-2-(trifluoromethyl)phenyl]carbamate 
• 379255-51-3 2-chloro-N-(4-nitro-2-(trifluoromethyl)phenyl)ethanamide 
• 59266-20-5 3-Tert-Butyl-2-Hydroxy-6-Methyl-N-(4-Nitro-2-Trifluoromethyl-Phenyl)-Benzamide 
• 691887-43-1 3-Tert-Butyl-5-Chloro-2-Hydroxy-6-Methyl-N-(4-Nitro-2-Trifluoromethyl-Phenyl)-Benzamide 
• 691887-50-0 3-Bromo-6-Hydroxy-5-Isopropyl-2-Methyl-N-(4-Nitro-2-Trifluoromethyl-Phenyl)-Benzamide 
• 691887-51-1 3-Bromo-5-Tert-Butyl-6-Hydroxy-2-Methyl-N-(4-Nitro-2-Trifluoromethyl-Phenyl)-Benzamide 
• 393-04-4 4-nitro-2-(trifluoromethyl)benzenesulfonamide 
• 37756-78-8 (4-nitro-2-trifluoromethyl-phenyl)-(tetrafluoro-pyridin-4-yl)-amine 
• 53393-23-0 2',4-bis(trifluoromethyl)-2,4',6-trinitrodiphenylamine 

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