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
• Article Data: 5

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

Chemical Properties

clear colorless to light yellow liquid

Uses

2-Bromo-5-(trifluoromethyl)aniline is used in the synthesis and biochemical evaluation of series of inhibitors of hepatitis C virus (HCV) NS3 protease.

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

• 891779-92-3 3-(2-bromo-5-trifluoromethylphenylamino)quinoline 
• 1451051-71-0 C₉H₇BrF₃NO₂ 
• 158461-46-2 2-(pyridin-2-yl)-5-(trifluoromethyl)aniline 

Relevant articles and documents

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