3862-73-5

Basic information

• Product Name: 2,3,4-Trifluorobenzenamine
• Synonyms: 2,3,4-TFA;2,3,4-TRIFLUOROANILINE;2,3,4-TRIFLUOROBENZENAMINE;2,3,4-TRIFLUORANILINE;2,3,4-trifluoro-anilin;2,3,4-trifluoro-benzenamin;TRIFLUOROANILINE;2,3,4-Trifluoroaniline99%
• CAS NO: 3862-73-5
• Molecular Formula: C₆H₄F₃N
• Molecular Weight: 147.1
• EINECS: 253-703-1
• Product Categories: Fluorine series;Anilines, Aromatic Amines and Nitro Compounds;Fluorobenzene;Amines;C2 to C6;Nitrogen Compounds
• Mol File: 3862-73-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 14-15°C
• Boiling Point: 92 °C48 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: Pale yellow liquid
• Density: 1.393 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00696mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.25±0.10(Predicted)
• BRN: 3245609
• CAS DataBase Reference: 2,3,4-Trifluorobenzenamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Trifluorobenzenamine(3862-73-5)
• EPA Substance Registry System: 2,3,4-Trifluorobenzenamine(3862-73-5)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 21/22-38-41-48/22-51/53
• Safety Statements: 23-26-36/37/39-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• RTECS: CY1211500
• F: 9
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 3862-73-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR PURPLE TO BROWN LIQUID

Uses

2,3,4-Trifluoroaniline was used in preparation of diethyl 2-(2,3,4-trifluoro)-phenylaminomethylene malonate.

General Description

Study on synthesis of 2,3,4-trifluoroaniline was reported.

Safety Profile

Moderately toxic by ingestion. Askin and eye irritant. Combustible liquid. When heated todecomposition it emits toxic fumes of NOx and F??.

InChI:InChI=1/C7H5F3N2O/c8-7(9,10)5-2-1-4(3-12-5)6(11)13/h1-3H,(H2,11,13)

Synthetic route

2,3,4-trifluoronitrobenzene (771-69-7) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
With sodium hypophosphite monohydrate; 1% platinum on charcoal; hydrogen at 65 - 80℃; under 6750.68 Torr; for 2.75h; Reagent/catalyst; Temperature; Autoclave;	98.52%
With hydrogen; nickel Autoclave;	91.8%
With iron; ammonium chloride

2,4-difluorophenylamine (367-25-9) → 2,4,5-trifluoroaniline (367-34-0) + 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
With trifluorormethanesulfonic acid; fluorine at 20℃; Title compound not separated from byproducts;

aniline (62-53-3) + α-chloro-propionic acid amide → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: F2; TfOH / 20 °C 2: F2; TfOH / 20 °C 3: F2; TfOH / 20 °C View Scheme

4-fluoroaniline (371-40-4) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: F2; TfOH / 20 °C 2: F2; TfOH / 20 °C View Scheme

1,3-dichloro-2-fluorobenzene (2268-05-5) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; aqueous nitric acid / 40 °C 2: dimethylformamide; potassium fluoride / 150 °C 3: iron; aqueous NH4Cl View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 2 h / Heating 2: sulfolane; potassium fluoride / 8 h / 200 - 210 °C 3: nickel; hydrogen / Autoclave View Scheme

1,3-dichloro-2-fluoro-4-nitrobenzene (393-79-3) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide; potassium fluoride / 150 °C 2: iron; aqueous NH4Cl View Scheme
Multi-step reaction with 2 steps 1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C 2: nickel; hydrogen / Autoclave View Scheme

2,3,4-trifluoronitrobenzene (771-69-7) → 3,4-difluoronitrobenzene (369-34-6) + 1,2-difluoro-3-nitrobenzene (6921-22-8) + 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
With Dimethylphenylsilane; o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In tetrahydrofuran for 12h; Inert atmosphere; Reflux; Overall yield = 95 %Spectr.; regioselective reaction;

3,4,5-trichloronitrobenzen (20098-48-0) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride / 11 h / 140 - 175 °C 2.1: hydrogen / methanol / Inert atmosphere 3.1: nitrosylsulfuric acid / 6 h / 10 - 15 °C 3.2: 1 h 4.1: sulfuric acid; nitric acid / 2 h / Heating 5.1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C 6.1: nickel; hydrogen / Autoclave View Scheme

3,5-dichloro-4-fluoro-nitrobenzene (3107-19-5) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogen / methanol / Inert atmosphere 2.1: nitrosylsulfuric acid / 6 h / 10 - 15 °C 2.2: 1 h 3.1: sulfuric acid; nitric acid / 2 h / Heating 4.1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C 5.1: nickel; hydrogen / Autoclave View Scheme

3,5-dichloro-4-fluorophenylamine (2729-34-2) → 2,3,4-trifluoroaniline (3862-73-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitrosylsulfuric acid / 6 h / 10 - 15 °C 1.2: 1 h 2.1: sulfuric acid; nitric acid / 2 h / Heating 3.1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C 4.1: nickel; hydrogen / Autoclave View Scheme

2,3,4-trifluoroaniline (3862-73-5) + acetic anhydride (108-24-7) → N-(2,3,4-trifluorophenyl)acetamide (365-29-7)

Conditions	Yield
In chloroform	99%
With dmap at 0 - 20℃; for 6.16667h;	95%
at 20℃; for 0.25h;	58%
With hydrogenchloride at 90℃;

2,3,4-trifluoroaniline (3862-73-5) + potassium ethyl xanthogenate (140-89-6) → 6,7-difluoro-2-mercaptobenzothiazole

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 0.133333h; microwave irradiation;	99%
In N,N-dimethyl-formamide at 120℃; for 4h;

2,3,4-trifluoroaniline (3862-73-5) + C11H18ClNO3 → tert-butyl (2S,3S)-2-methyl-3-((2,3,4-trifluorophenyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere;	99%

2,3,4-trifluoroaniline (3862-73-5) + 4-chloro-2-methylquinoline (4295-06-1) → C16H11F3N2 (1334225-28-3)

Conditions	Yield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; for 20h; Buchwald-Hartwig amination; Inert atmosphere; chemoselective reaction;	95%

2,3,4-trifluoroaniline (3862-73-5) → (2,3,4-trifluorophenyl)hydrazine hydrochloride

Conditions	Yield
Stage #1: 2,3,4-trifluoroaniline With magnesium nitrite In water at 30℃; Acidic conditions; Flow reactor; Stage #2: With sodium sulfite In water at 90 - 110℃; Stage #3: With hydrogenchloride In water at 120℃;	95%

2,3,4-trifluoroaniline (3862-73-5) + 2-Bromoacetyl bromide (598-21-0) → C8H5BrF3NO

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0℃; for 1h;	95%
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 1h;

2,3,4-trifluoroaniline (3862-73-5) + potassium ethyl xanthogenate (140-89-6) + alpha-bromo-3,4-difluorotoluene (85118-01-0) → 2-(3,4-difluoro-benzylsulfanyl)-6,7-difluoro-benzothiazole

Conditions	Yield
Stage #1: 2,3,4-trifluoroaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 120℃; for 0.133333h; microwave irradiation; Stage #2: alpha-bromo-3,4-difluorotoluene In N,N-dimethyl-formamide at 90℃; for 0.1h; microwave irradiation;	93%

2,3,4-trifluoroaniline (3862-73-5) → C6H2F3NOS (530102-75-1)

Conditions	Yield
With thionyl chloride In benzene Michaelis reaction;	92%

o-fluorobenzyl bromide (446-48-0) + 2,3,4-trifluoroaniline (3862-73-5) + potassium ethyl xanthogenate (140-89-6) → 6,7-difluoro-2-(2-fluoro-benzylsulfanyl)-benzothiazole

Conditions	Yield
Stage #1: 2,3,4-trifluoroaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 120℃; for 0.133333h; microwave irradiation; Stage #2: o-fluorobenzyl bromide In N,N-dimethyl-formamide at 90℃; for 0.1h; microwave irradiation;	92%

2,3,4-trifluoroaniline (3862-73-5) + 2,3,4-trifluorophenyl isothiocyanate (119474-40-7) → N,N'-Di(2,3,4-trifluorophenyl)thiourea (354151-69-2)

Conditions	Yield
In ethanol at 20℃;	91%
In ethanol at 20℃; for 8h;

o-iodo-methyl-benzoic acid (610-97-9) + 2,3,4-trifluoroaniline (3862-73-5) → methyl 2-(2,3,4-trifluoroanilino)benzoate (741281-01-6)

Conditions	Yield
With DPE-Phos; caesium carbonate; palladium diacetate In toluene at 95℃; for 48h; Buchwald-Hartwig amination reaction;	91%

2,3,4-trifluoroaniline (3862-73-5) + 1,2,3-thiadiazole-5-carbonyl azide (58756-32-4) → 1-(2,3,4-trifluorophenyl)-3-(1',2',3'-thiadiazol-5'-yl)urea

Conditions	Yield
In toluene Heating;	91%

2,3,4-trifluoroaniline (3862-73-5) + butyraldehyde (123-72-8) → N,N-dibutyl-2,3,4-trifluorobenzeneamine

Conditions	Yield
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran for 1.66667h; Ambient temperature;	90%

2,6-Difluorobenzyl bromide (85118-00-9) + 2,3,4-trifluoroaniline (3862-73-5) + potassium ethyl xanthogenate (140-89-6) → 2-(2,6-difluoro-benzylsulfanyl)-6,7-difluoro-benzothiazole

Conditions	Yield
Stage #1: 2,3,4-trifluoroaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 120℃; for 0.133333h; microwave irradiation; Stage #2: 2,6-Difluorobenzyl bromide In N,N-dimethyl-formamide at 90℃; for 0.1h; microwave irradiation;	90%

2,3,4-trifluoroaniline (3862-73-5) + cyanoacetic acid (372-09-8) → 2-cyano-N-[(2,3,4-trifluoro)phenyl]acetamide (239081-10-8)

Conditions	Yield
Stage #1: cyanoacetic acid With phosphorus pentachloride In dichloromethane for 0.5h; Reflux; Stage #2: 2,3,4-trifluoroaniline In dichloromethane for 2h; Reflux;	90%

2,3,4-trifluoroaniline (3862-73-5) + 4-hydroxy-benzaldehyde (123-08-0) → 4-((E)-(2,3,4-trifluorophenylimino)methyl)phenol

Conditions	Yield
In ethanol at 20℃; for 72h; Molecular sieve; Inert atmosphere;	90%

2,3,4-trifluoroaniline (3862-73-5) + butyraldehyde (123-72-8) → N,N-di<(1-deuterio)butyl>-2,3,4-trifluorobenzeneamine

Conditions	Yield
With sodium borodeuteride; sulfuric acid In tetrahydrofuran for 1.66667h; Ambient temperature;	89%

carbon disulfide (75-15-0) + 2,3,4-trifluoroaniline (3862-73-5) + triethylamine (121-44-8) → triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (119474-39-4)

Conditions	Yield
for 144h; Ambient temperature;	89%
for 80h; Ambient temperature;	87%

2,3,4-trifluoroaniline (3862-73-5) + potassium ethyl xanthogenate (140-89-6) → 6,7-difluoro-1,3-benzothiazole-2(3H)-thione

Conditions	Yield
In N,N-dimethyl-formamide for 1h; Heating;	89%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 2,3,4-trifluoroaniline (3862-73-5) → N-2,3,4-trifluorophenyl-3,5-di-tert-butylsalicylaldimine (1229248-02-5)

Conditions	Yield
With formic acid In ethanol for 36h; Reflux;	88%
With formic acid In ethanol Reflux;

2,3,4-trifluoroaniline (3862-73-5) → 2,3,4-trifluoro-6-iodoaniline

Conditions	Yield
With iodine; iodic acid In 1,4-dioxane; water for 5h; Reflux;	88%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 3h;	38%

2,3,4-trifluoroaniline (3862-73-5) + 4-Methanesulfonyl-benzoyl isothiocyanate → N-(4-methylsulfonylbenzoyl)-N'-(2,3,4-trifluorophenyl)thiourea

Conditions	Yield
at 20℃;	87%

2,3,4-trifluoroaniline (3862-73-5) + potassium thioacyanate (333-20-0) → 4,5,6-trifluoro-2-benzothiazolamine

Conditions	Yield
With bromine; acetic acid at 20℃; for 8h; Cooling with ice;	86.8%

2,3,4-trifluoroaniline (3862-73-5) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-((2,3,4-trifluorophenylamino)methylene)malonate (100501-60-8)

Conditions	Yield
for 2h; Heating;	86%
at 120 - 130℃; for 3h;	80%
at 110 - 120℃; for 2h;	74%

2,3,4-trifluoroaniline (3862-73-5) + 4-heptylbenzoic acid 4-formylphenyl ester (503446-72-8) → 6APE

Conditions	Yield
With acetic acid In ethanol for 7h; Reflux;	86%

5-isocyanato-1H-indole-adamantane + 2,3,4-trifluoroaniline (3862-73-5) → C25H24F3N3O

Conditions	Yield
In toluene at 60℃; for 4h;	85.8%

bis(benzonitrile)palladium(II) chloride (14220-64-5, 39958-10-6, 15617-18-2) + 2,3,4-trifluoroaniline (3862-73-5) → trans-[PdCl2(2,3,4-trifluoroaniline)2] (919990-61-7)

Conditions	Yield
In ethanol under N2; soln. of PdCl2(C6H5CN)2 (0.26 mmol) added to soln. of 2,3,5-trifluoroaniline (0.52 mmol); refluxed (8 h); hot soln. filtered; solvent removed (vac.); elem. anal.;	85%

2,3,4-trifluoroaniline (3862-73-5) + ethyl ({4-[2-(5-methylpyrazine-2-carboxamido)ethyl]phenyl}sulfonyl)carbamate → 5-methyl-N-(4-{N-[(2,3,4-trifluorophenyl)carbamoyl]sulfamoyl}phenethyl)pyrazine-2-carboxamide

Conditions	Yield
In toluene for 4h; Reflux;	84.2%

2,3,4-trifluoroaniline (3862-73-5) + ethyl 3-(2-acetoxy-3,5-dibromophenyl)-2-(3,4-dimethoxybenzamido)acrylate → 2,4-dibromo-6-(2-(3,4-dimethoxybenzamido)-3-oxo-3-(2,3,4-trifluorophenylamino)prop-1-enyl)phenyl acetate

Conditions	Yield
In tetrahydrofuran at 0 - 5℃; for 2h;	83.11%

Upstream product

• 36556-42-0 4-chloro-1,2,3-trifluorobenzene 
• 2729-34-2 3,5-dichloro-4-fluorophenylamine 
• 3107-19-5 3,5-dichloro-4-fluoro-nitrobenzene 
• 20098-48-0 3,4,5-trichloronitrobenzen 
• 771-69-7 2,3,4-trifluoronitrobenzene 
• 393-79-3 1,3-dichloro-2-fluoro-4-nitrobenzene 
• 2268-05-5 1,3-dichloro-2-fluorobenzene 
• 371-40-4 4-fluoroaniline 
• 62-53-3 aniline 
• 367-25-9 2,4-difluorophenylamine 

Downstream Products

• 2822-41-5 2,3,4-trifluorophenol 
• 741281-09-4 methyl 2-(2,3,4-trfluoroanilino)-5-nitrobenzoate 
• 741281-05-0 methyl 4-chloro-2-(2,3,4-trifluoroanilino)benzoic acid 
• 103-84-4 Acetanilid 
• 170098-76-7 5,6,7-trifluoro-1,4-dihydroquinoxaline-2,3-dione 
• 144367-60-2 2-cyano-3-(2,3,4-trifluorophenyl)aminoacrylic acid ethyl ester 
• 741281-01-6 methyl 2-(2,3,4-trifluoroanilino)benzoate 
• 119474-40-7 2,3,4-trifluorophenyl isothiocyanate 
• 94242-49-6 N-cyclopropyl-2,3,4-trifluoroaniline 
• 530102-75-1 C₆H₂F₃NOS 

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