454-79-5

Basic information

• Product Name: 2-Bromo-5-(trifluoromethyl)aniline
• Synonyms: 3-Amino-4-bromobenzotrifluoride (2-Bromo-5-trifluoromethylaniline);2-AMINO-4-TRIFLUOROMETHYLBROMOBENZENE;3-Amino-4-bromobenzotrifluoride 98%;3-Amino-4-bromobenzotrifluoride98%;2-BROMO-5-(TRIFLUOROMETHYL)ANILIME;2-BROMO-5-(TRIFLUOROMETHYL)ANILINE/3-AMINO-4-BROMOBENZOTRIFLUORIDE/;2-amino-4-trifluoromthylbromobenzene;2-Bromo-5-trifluoromethylphenylamine
• CAS NO: 454-79-5
• Molecular Formula: C₇H₅BrF₃N
• Molecular Weight: 240.02
• EINECS: 207-227-6
• Product Categories: Amines and Anilines;Halides;Aniline;Miscellaneous;Amines;C7;Nitrogen Compounds;Aniline series;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 454-79-5.mol

Chemical Properties

• Melting Point: 47-49°C
• Boiling Point: 81-82 °C
• Flash Point: >230 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.675 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.036mmHg at 25°C
• Refractive Index: n20/D 1.522(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.31±0.10(Predicted)
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 2094535
• CAS DataBase Reference: 2-Bromo-5-(trifluoromethyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-(trifluoromethyl)aniline(454-79-5)
• EPA Substance Registry System: 2-Bromo-5-(trifluoromethyl)aniline(454-79-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-27-36/37/39-45-37/39
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 454-79-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-5-(trifluoromethyl)aniline is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly for the development of inhibitors targeting the hepatitis C virus (HCV) NS3 protease. Its unique structural features contribute to the design and optimization of potent and selective inhibitors, which can potentially lead to effective treatments for HCV infections.
Additionally, due to its reactivity and structural diversity, 2-Bromo-5-(trifluoromethyl)aniline can be employed in the synthesis of other bioactive molecules, further expanding its applications in the pharmaceutical industry for the development of novel therapeutic agents.

InChI:InChI=1/C7H6F3NO/c8-7(9,10)4-1-2-5(11)6(12)3-4/h1-3,12H,11H2

Synthetic route

1-bromo-4-trifluoromethyl-2-nitrobenzene (349-03-1) → 2-Bromo-5-trifluoromethylaniline (454-79-5)

Conditions	Yield
With iron; ammonium chloride In ethanol; water for 1h; Reflux;	58%
With tin(ll) chloride

3-trifluoromethylaniline (98-16-8) → 2-Bromo-5-trifluoromethylaniline (454-79-5) + 4-bromo-3-(trifluoromethyl)aniline (393-36-2)

Conditions	Yield
With tetrabutylammomium bromide; copper(ll) bromide In ethanol at 45℃; regioselective reaction;	A 28% B 33%
With bromine; acetic acid

3-trifluoromethylaniline (98-16-8) → 2-Bromo-5-trifluoromethylaniline (454-79-5)

Conditions	Yield
With bromine; iron

3-trifluoromethylaniline (98-16-8) → 2-Bromo-5-trifluoromethylaniline (454-79-5) + bromo-3-(trifluoromethyl)-aniline (58458-10-9) + 4-bromo-3-(trifluoromethyl)aniline (393-36-2)

Conditions	Yield
With N-Bromosuccinimide In 1,4-dioxane at 20℃;	A 32 %Chromat. B 36 %Chromat. C 32 %Chromat.
With N-Bromosuccinimide In EtCN at 20℃;	A 8 %Chromat. B 12 %Chromat. C 80 %Chromat.

2-Bromo-5-trifluoromethylaniline (454-79-5) + chloroformic acid ethyl ester (541-41-3) → N-(2-bromo-5-trifluoromethylphenyl)carbamic acid ethyl ester (336608-64-1)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 3h;	100%
With pyridine In diethyl ether; water at 20℃; for 18h; Cooling with ice;

2-Bromo-5-trifluoromethylaniline (454-79-5) + 3-pyridylboronic acid (1692-25-7) → 2-(pyridin-3-yl)-5-(trifluoromethyl)benzeneamine (158461-54-2)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki cross-coupling; Inert atmosphere;	100%
With sodium carbonate; trans-bis(triphenylphosphine)palladium dichloride In 1,4-dioxane; water for 24h; Suzuki cross-coupling; Heating;	91%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 100℃; for 14h; Inert atmosphere;	7.62 g
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; Inert atmosphere;

2-Bromo-5-trifluoromethylaniline (454-79-5) + potassium ethyl xanthogenate (140-89-6) → 2-mercapto-5-(trifluoromethyl)benzothiazole (23420-87-3)

Conditions	Yield
With copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 6h; Inert atmosphere; Sealed tube;	98.1%
In N,N-dimethyl-formamide for 4h; Heating / reflux;	92%
Stage #1: 2-Bromo-5-trifluoromethylaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 130℃; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 0.5h;	91%

2-Bromo-5-trifluoromethylaniline (454-79-5) + acetyl chloride (75-36-5) → N-(2-bromo-5-(trifluoromethyl)phenyl)acetamide (331005-35-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	98%
With sodium hydrogencarbonate; triethylamine In dichloromethane at 0 - 20℃; for 2h;	75.6%
In ethyl acetate at 85℃;	71%
In ethyl acetate Heating;
In dichloromethane at 20℃; for 24h;

2-Bromo-5-trifluoromethylaniline (454-79-5) + benzoyl chloride (98-88-4) → N-(2-bromo-5-(trifluoromethyl)phenyl)benzamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h;	97%
In dichloromethane at 20℃; for 24h;

2-Bromo-5-trifluoromethylaniline (454-79-5) + tris-iso-propylsilyl acetylene (89343-06-6) → 5-(trifluoromethyl)-2-((triisopropylsilyl)ethynyl)aniline

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 100℃; Sonogashira Cross-Coupling; Inert atmosphere;	97%

di-tert-butyl dicarbonate (24424-99-5) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → N,N'-bis(tert-butyloxycarbonyl)-2-bromo-5-trifluoromethylaniline (880384-45-2)

Conditions	Yield
In tetrahydrofuran Heating;	96%
With dmap In tetrahydrofuran at 20℃;	96%
With dmap In tetrahydrofuran Heating;

5-methylfuran-2-boronic acid (62306-79-0) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → 2-(5-methylfuran-2-yl)-5-(trifluoromethyl)aniline

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;	95%

2-Bromo-5-trifluoromethylaniline (454-79-5) + trans-2-phenylvinylboronic acid (6783-05-7) → (E)-2-styryl-5-(trifluoromethyl)aniline (1054567-68-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux;	94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 16h; Suzuki Coupling; Inert atmosphere;	81%

(E)-1-octen-1-ylboronic acid (42599-16-6) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → (E)-2-(oct-1-enyl)-5-(trifluoromethyl)aniline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 20h; Reflux; Inert atmosphere;	94%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 2-(5-fluoro-thiophen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane → 2-(5-fluorothiophen-2-yl)-5-(trifluoromethyl)aniline

Conditions	Yield
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; for 1h; Inert atmosphere;	94%

2-phenylimidazo[2,1-b]benzothiazole (17833-07-7) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → (E)-3-((2-bromo-5-(trifluoromethyl)phenyl)diazenyl)-2-phenylbenzo[d]imidazo[2,1-b]thiazole

Conditions	Yield
With tert.-butylnitrite In ethanol at 20℃; for 1h; Green chemistry;	93%

formic acid (64-18-6) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → N-(2-bromo-5-(trifluoromethyl)phenyl)formamide (1536478-90-6)

Conditions	Yield
In toluene at 100℃; for 16h;	93%
With acetic anhydride In dichloromethane at 20℃; for 2h; Inert atmosphere;	91%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 4,4'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-amine

Conditions	Yield
With palladium diacetate; diisopropylamine In water at 100℃; for 0.5h; Suzuki-Miyaura Coupling;	93%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 96℃; for 24h; Inert atmosphere;	85%

2-Bromo-5-trifluoromethylaniline (454-79-5) + acetic anhydride (108-24-7) → N-(2-bromo-5-(trifluoromethyl)phenyl)acetamide (331005-35-7)

Conditions	Yield
With dmap In chloroform for 24h; Reflux;	93%

2-Bromo-5-trifluoromethylaniline (454-79-5) → 2-mercapto-5-(trifluoromethyl)benzothiazole (23420-87-3)

Conditions	Yield
In chloroform; N,N-dimethyl-formamide	92%

2-Bromo-5-trifluoromethylaniline (454-79-5) + Propiolic acid (471-25-0) → N-(2-bromo-5-(trifluoromethyl)phenyl)propiolamide (1477484-83-5)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	92%

2-Bromo-5-trifluoromethylaniline (454-79-5) + acrylic acid methyl ester (292638-85-8) → C11H10F3NO2

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 90℃; for 16h; Heck Reaction; Inert atmosphere; Sealed tube;	92%

2-Bromo-5-trifluoromethylaniline (454-79-5) + phenylacetylene (536-74-3) → 2-(phenylethynyl)-5-(trifluoromethyl)aniline (1181455-55-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; ethanolamine In tetrahydrofuran; water for 19h; Sonogashira coupling; Inert atmosphere; Reflux;	91%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; Sonogashira Cross-Coupling; Inert atmosphere;	75%
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 80℃; for 48h; Sonogashira coupling; Inert atmosphere;	54%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 4-methoxyphenylboronic acid (5720-07-0) → 4'-methoxy-4-(trifluoromethyl)-[1,1'-biphenyl]-2-amine (700802-70-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 16h;	91%

thiophene boronic acid (6165-68-0) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → 2-(thiophen-2-yl)-5-(trifluoromethyl)aniline

Conditions	Yield
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; Inert atmosphere;	91%
Stage #1: thiophene boronic acid; 2-Bromo-5-trifluoromethylaniline With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20℃; for 1.5h; Inert atmosphere; Stage #2: With sodium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;	75%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 2-iodobiphenyl (2113-51-1) → 7-(trifluoromethyl)-9H-tribenzo[b,d,f]azepine

Conditions	Yield
With palladium diacetate; tetra-(n-butyl)ammonium iodide; caesium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 36h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	89%

2-Bromo-5-trifluoromethylaniline (454-79-5) + (2S,4R)-1-((S)-2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carboxylic acid (445306-08-1) → C39H42BrF3N4O6 (1028412-38-5)

Conditions	Yield
With pyridine; trichlorophosphate at -15 - 20℃;	88%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 2-nitro-benzaldehyde (552-89-6) → N-(2-nitrobenzylidene)-2-bromo-5-trifluoromethylaniline (1453279-85-0)

Conditions	Yield
In isopropyl alcohol for 0.166667h; Reflux;	88%

2-Bromo-5-trifluoromethylaniline (454-79-5) + α-trifluoromethylmaleic anhydride (700-27-6) → 1-(2-bromo-5-trifluoromethylphenyl)-3-trifluoromethyl-1H-pyrrole-2,5-dione

Conditions	Yield
With acetic acid Reflux;	88%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 3-fluorophenylboronic acid (768-35-4) → 3'-fluoro-4-(trifluoromethyl)-[1,1'-biphenyl]-2-amine

Conditions	Yield
With palladium diacetate; diisopropylamine In water at 100℃; for 0.5h; Suzuki-Miyaura Coupling;	88%
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; Inert atmosphere;	78%

2-hydroxymethyl-4-methylphenol (4383-07-7) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → 2-methyl-8-trifluoromethyldibenz[b,f][1,4]oxazepin-11(10H)-one

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; potassium hydroxide; copper(I) bromide In 1,4-dioxane at 110℃; for 30h;	87%

citraconic acid anhydride (616-02-4) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → 1-(2-bromo-5-trifluoromethylphenyl)-3-methyl-1H-pyrrole-2,5-dione

Conditions	Yield
With acetic acid Reflux;	87%

2-iodo-propane (75-30-9) + 2-Bromo-5-trifluoromethylaniline (454-79-5) → 2-bromo-N-isopropyl-5-(trifluoromethyl)aniline

Conditions	Yield
Stage #1: 2-Bromo-5-trifluoromethylaniline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 2-iodo-propane In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	86%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 2-Methoxybenzoyl chloride (21615-34-9) → 2-(2-methoxyphenyl)-5-trifluoromethylbenzoxazole (1021439-40-6)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In acetonitrile at 210℃; for 0.25h; microwave irradiation;	85%

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 349-03-1 1-bromo-4-trifluoromethyl-2-nitrobenzene 

Downstream Products

• 880384-45-2 N,N'-bis(tert-butyloxycarbonyl)-2-bromo-5-trifluoromethylaniline 
• 1309358-86-8 N-[2-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-phenylcyclopropane-carboxamide 
• 1181455-56-0 C₁₆H₁₂F₃NO 
• 1181455-55-9 5-(trifluoromethyl)-2-(phenylethynyl)aniline 
• 1181455-57-1 C₁₅H₉F₄N 
• 1240382-27-7 C₁₇H₂₀BrF₃N₂O₃ 
• 1207887-03-3 2-bromo-N-(2-nitrophenyl)-5-(trifluoromethyl)aniline 
• 739361-61-6 2-bromo-5-trifluoromethylphenylhydrazine 
• 1198007-18-9 N,N'-bis(2-bromo-5-trifluoromethylphenyl)formamidine 
• 1171909-15-1 2-{[2-bromo-5-(trifluoromethyl)phenyl]amino}-2-methylpropane-1-thiol 
• 1171909-12-8 1-{[2-bromo-5-(trifluoromethyl)phenyl]amino}-2-methylpropane-2-thiol 
• 1123762-11-7 N-(1'-ethoxy)cyclopropyl-2-bromo-5-trifluoromethylaniline 
• 384793-21-9 (2-bromo-5-trifluoromethylphenyl)-carbamic acid tert-butyl ester 
• 1196972-92-5 5-(trifluoromethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine 

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