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

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

Uses

Used in Dye Synthesis:
2-Amino-5-nitrobenzotrifluoride is used as a key intermediate in the synthesis of monoazo dyes. Its unique chemical structure allows it to participate in diazotization and coupling reactions with various other compounds, such as N-hydroxyalkylamino-5-naphtholspyrazolones, naphtholsulphonic acids, and N-(2-cyanoethyl)-N-(hydroxyalkyl)anilines, resulting in the formation of a diverse range of monoazo dyes with different colors and properties.
Used in Chemical Research:
Due to its reactivity and the presence of multiple functional groups, 2-Amino-5-nitrobenzotrifluoride is also utilized in chemical research for the development of new compounds and the study of reaction mechanisms. Its ability to undergo diazotization and coupling reactions makes it a valuable tool for exploring new synthetic pathways and understanding the behavior of various functional groups in organic chemistry.

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

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

Downstream Products

• 400-67-9 2-chloro-4-nitro-6-trifluoromethyl-aniline 
• 400-75-9 1-iodo-4-nitro-2-(trifluoromethyl)benzene 
• 400-66-8 2-bromo-4-nitro-6-trifluoromethylaniline 
• 53393-23-0 2',4-bis(trifluoromethyl)-2,4',6-trinitrodiphenylamine 
• 13277-18-4 N-Nonanoyl-4-nitro-2-trifluormethyl-anilin 
• 53446-58-5 3,5-Dinitro-4-(4-nitro-2-trifluoromethyl-phenylamino)-benzonitrile 
• 68105-51-1 (2,4-Dinitro-naphthalen-1-yl)-(4-nitro-2-trifluoromethyl-phenyl)-amine 
• 54179-93-0 C₄₈H₅₀F₃N₅O₈S 
• 72773-11-6 (4-Nitro-2,6-bis-trifluoromethyl-phenyl)-(4-nitro-2-trifluoromethyl-phenyl)-amine 
• 92524-78-2 5-(4-Chloro-benzoyl)-2-hydroxy-3-methyl-N-(4-nitro-2-trifluoromethyl-phenyl)-benzamide 
• 367-67-9 2-bromo-5-nitro-benzotrifluoride 
• 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 

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O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields, ortho- or para-Animation with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c-f, 14 and 22g.

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.

Process for the preparation of aromatic amines

Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.