656-65-5

Basic information

• Product Name: 4-Bromo-3-fluoroaniline
• Synonyms: 4-BROMO-3-FLUOROPHENYLAMINE;4-BROMO-3-FLUOROANILINE;4-Bromo-3-fluoroaniline98%;4-Bromo-3-fluorobenzenamine;4-Bromo-3-fluoroanil;4-BroMo-3-fluoroaniline, 98% 5GR;4-BroMo-3-fluoroaniline, 97+%;4 - broMine - 3 - fluoro aniline
• CAS NO: 656-65-5
• Molecular Formula: C₆H₅BrFN
• Molecular Weight: 190.01
• EINECS: -0
• Product Categories: Amines;blocks;Bromides;FluoroCompounds;Fluorobenzene;Anilines, Aromatic Amines and Nitro Compounds;Aniline;Anilines, Amides & Amines;Bromine Compounds;Fluorine Compounds;Phenyls & Phenyl-Het;C2 to C6;Nitrogen Compounds;Aryl Fluorinated Building Blocks;Building Blocks;C6;Chemical Synthesis;Fluorinated Building Blocks;Nitrogen Compounds;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks
• Mol File: 656-65-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 72-73°C
• Boiling Point: 65-68 °C(lit.)
• Flash Point: 105 °F
• Appearance: Yellow to tan/Crystalline Powder
• Density: 0.982 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.471(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetonitrile, Methanol
• PKA: 2.88±0.10(Predicted)
• Water Solubility: Soluble in acetonitrile, methanol. Insoluble in water.
• BRN: 3236457
• CAS DataBase Reference: 4-Bromo-3-fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3-fluoroaniline(656-65-5)
• EPA Substance Registry System: 4-Bromo-3-fluoroaniline(656-65-5)

Safety Data

• Hazard Codes: Xi,T,Xn
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 656-65-5(Hazardous Substances Data)

Usage

Chemical Properties

Beige to brown needles and crystalline powder

Uses

Different sources of media describe the Uses of 656-65-5 differently. You can refer to the following data:
1. 4-Bromo-3-fluoroaniline is a intermediate used for the synthetic preparation of Tradizolid and various pharmaceuticals such as the synthesis of several lateral difluoro-substituted 4,4"-dialkyl- and 4 ,4"-alkoxyalkylterphenyls.
2. 4-Bromo-3-fluoroaniline is an intermediate used for the synthetic preparation of Tradizolid and various pharmaceuticals such as the synthesis of several lateral difluoro-substituted 4,4"-dialkyl- and 4,4"-alkoxyalkylterphenyls.

Synthetic route

N-(4-bromo-3-fluorophenyl)ethanamide (351-30-4) → 3-fluoro-4-bromophenylamine (656-65-5)

Conditions	Yield
With hydrogenchloride; water In ethanol at 80℃; for 4h;	100%
With hydrogenchloride In ethanol for 2h; Heating;	99%

meta-fluoroaniline (372-19-0) → 3-fluoro-4-bromophenylamine (656-65-5)

Conditions	Yield
With 1-hexyl-3-methyl-1-imidazolium bromide; copper(ll) bromide for 0.166667h; regioselective reaction;	90%
With tetrabutylammomium bromide; copper(ll) bromide In ethanol at 25℃; regioselective reaction;	80%
Multi-step reaction with 3 steps 1: 70 percent / acetic acid / 0.33 h / Heating 2: 100 percent / NBS / CH2Cl2 / a) reflux, 5 h, b) room temp., 16 h 3: 99 percent / 36percent HCl / ethanol / 2 h / Heating View Scheme
With N-Bromosuccinimide In dimethyl sulfoxide at 20℃; regioselective reaction;	> 95 %Chromat.
Multi-step reaction with 3 steps 1: acetic acid / 3 h / 105 °C 2: N-Bromosuccinimide / dichloromethane / 24 h / 60 °C 3: hydrogenchloride; water / ethanol / 4 h / 80 °C View Scheme

4-bromo-3-fluorobenzonitrile (133059-44-6) → 3-fluoro-4-bromophenylamine (656-65-5)

Conditions	Yield
Stage #1: 4-bromo-3-fluorobenzonitrile With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at -5 - 5℃; for 2h; Stage #2: With sodium hypochlorite In water at -5 - 5℃; for 8h; Temperature;	79%

N-(3-fluorophenyl)acetamide (351-28-0) → 3-fluoro-4-bromophenylamine (656-65-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / NBS / CH2Cl2 / a) reflux, 5 h, b) room temp., 16 h 2: 99 percent / 36percent HCl / ethanol / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: N-bromo-succinimide View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 24 h / 60 °C 2: hydrogenchloride; water / ethanol / 4 h / 80 °C View Scheme

meta-fluoroaniline (372-19-0) → 2-bromo-5-fluoroaniline (1003-99-2) + 3-fluoro-4-bromophenylamine (656-65-5)

Conditions	Yield
With N-Bromosuccinimide In DCE at 20℃;	A 11 %Chromat. B 89 %Chromat.

3,4-Difluorobenzonitrile (64248-62-0) → 3-fluoro-4-bromophenylamine (656-65-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonia / ethanol / 24 h / 70 - 80 °C 2.1: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 4 h / -5 - 5 °C 3.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran / 2 h / -5 - 5 °C 3.2: 8 h / -5 - 5 °C View Scheme

di-tert-butyl dicarbonate (24424-99-5) + 3-fluoro-4-bromophenylamine (656-65-5) → tert-butyl N-(4-bromo-3-fluorophenyl)carbamate (868735-43-7)

Conditions	Yield
In 1,4-dioxane; water at 80℃;	100%
In water at 20℃; for 40h;	94%
In water at 20℃; for 16h;	76%

3-fluoro-4-bromophenylamine (656-65-5) + trifluoroacetic anhydride (407-25-0) → N-(4-bromo-5-fluoro-2-nitrophenyl)-2,2,2-trifluoroacetamide (929279-27-6)

Conditions	Yield
Stage #1: 3-fluoro-4-bromophenylamine; trifluoroacetic anhydride at 0℃; for 0.5h; Stage #2: With potassium nitrate at 0 - 25℃;	100%
With ammonium nitrate In chloroform for 2h;	95%
Stage #1: 3-fluoro-4-bromophenylamine; trifluoroacetic anhydride With ammonium nitrate In chloroform at 20℃; for 2.16667h; Stage #2: With sodium hydrogencarbonate In chloroform; water pH=~ 8;	95%

3-fluoro-4-bromophenylamine (656-65-5) + benzyl chloroformate (501-53-1) → (4-bromo-3-fluorophenyl)carbamic acid benzyl ester (510729-01-8)

Conditions	Yield
With sodium hydrogencarbonate In acetone at 15 - 22℃; for 1.5h;	100%
Stage #1: 3-fluoro-4-bromophenylamine With sodium hydrogencarbonate In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: benzyl chloroformate In tetrahydrofuran at 0℃; for 3h;	100%
With sodium hydrogencarbonate In water; acetone at 0 - 20℃; for 24h;	94%

hexamethylene imine (111-49-9) + 3-fluoro-4-bromophenylamine (656-65-5) + 4-bromophenyl isocyanate (2493-02-9) → 5-azepan-1-yl-pentanoic acid (4-bromo-3-fluoro-phenyl)-amide (948883-08-7)

Conditions	Yield
Stage #1: 3-fluoro-4-bromophenylamine; 4-bromophenyl isocyanate With triethylamine In dichloromethane at 20℃; for 2h; Stage #2: hexamethylene imine With triethylamine In 1,2-dichloro-ethane at 55℃; for 4h;	100%

(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid (860617-71-6) + 3-fluoro-4-bromophenylamine (656-65-5) → 5-(4-amino-2-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (922505-85-9)

Conditions	Yield
Stage #1: (5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid; 3-fluoro-4-bromophenylamine With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran for 0.166667h; Stage #2: tri-tert-butyl phosphine In tetrahydrofuran; hexanes at 25℃; for 16h;	98%
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; hexanes at 25℃; for 16.08h;	98%
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran	27%

3-fluoro-4-bromophenylamine (656-65-5) + ethyl acrylate (140-88-5) → ethyl (2E)-3-(4-amino-2-fluorophenyl)prop-2-enoate (865137-76-4)

Conditions	Yield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 110℃; for 5h; Heck reaction; Inert atmosphere;	96%
With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 80℃; for 4h; Heck reaction; Inert atmosphere;	86%
With N-ethyl-N,N-diisopropylamine; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 110℃; for 5h; Mitsunobu reaction;
With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 5h;

2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (660867-80-1) + 3-fluoro-4-bromophenylamine (656-65-5) → 3-fluoro-4-(2-methylpyridin-4-yl)aniline (1314787-88-6)

Conditions	Yield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; for 16h;	96%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; for 16h;	96%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; for 16h;	96%

3-fluoro-4-bromophenylamine (656-65-5) + methyl chloroformate (79-22-1) → (4-bromo-3-fluoro-phenyl)-carbamic acid methyl ester (396076-65-6)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 5h;	94.3%
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 4.5h; Inert atmosphere;	92%
With pyridine In dichloromethane at 25℃; for 2h;	84.6%

3-fluoro-4-bromophenylamine (656-65-5) + phenylacetylene (536-74-3) → 3-fluoro-4-(phenylethynyl)aniline

Conditions	Yield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 20℃; for 5h; Sonogashira Cross-Coupling;	94%

1,2-bis-(chlorodimethylsilyl)ethane (13528-93-3) + 3-fluoro-4-bromophenylamine (656-65-5) → 1-(4-bromo-3-fluorophenyl)-2,2,5,5-tetramethyl-1,2,5-azadisilalidine (195817-59-5)

Conditions	Yield
With triethylamine In dichloromethane	93%
With triethylamine In dichloromethane for 48h;	93%

3-fluoro-4-bromophenylamine (656-65-5) + methanesulfonyl chloride (124-63-0) → N-(4-bromo-3-fluoro-phenyl)-methanesulfonamide (879486-59-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	93%
In pyridine; ethyl acetate	1.235 g (88%)

3-fluoro-4-bromophenylamine (656-65-5) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,3',4',5'-tetrafluoro-4-benzidine

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); potassium carbonate In water; N,N-dimethyl-formamide for 6h; Reagent/catalyst; Reflux; Inert atmosphere;	91.3%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 3-fluoro-4-bromophenylamine (656-65-5) → N-(4-bromo-3-fluorophenyl)-5-chloro-2-hydroxybenzamide (1000054-74-9)

Conditions	Yield
With phosphorus trichloride In toluene for 2h; Heating / reflux;	90%

3-fluoro-4-bromophenylamine (656-65-5) → 4-bromo-5-fluoro-2-iodoaniline (1219741-79-3)

Conditions	Yield
With N-iodo-succinimide In acetic acid at 25℃; for 1.5h;	90%
With N-iodo-succinimide; acetic acid In ethyl acetate at 20℃; for 1.5h;	87%
With N-iodo-succinimide; acetic acid at 0℃;	62.5%

3-fluoro-4-bromophenylamine (656-65-5) → C6H3BrFN3 (1492715-10-2)

Conditions	Yield
With hydrogenchloride; sodium azide; sodium nitrite In water at 0 - 5℃; for 2h;	89%
With hydrogenchloride; sodium azide; sodium nitrite In water at 0 - 20℃; for 2h;

C8H6F3O3S2(1-)*Na(1+) + 3-fluoro-4-bromophenylamine (656-65-5) → N-(4-bromo-3-fluorophenyl)-4-(trifluoromethyl)-benzothioamide

Conditions	Yield
With 1H-imidazole; sodium carbonate; dimethyl sulfoxide at 135℃; for 48h; Inert atmosphere; Schlenk technique;	86%

3-fluoro-4-bromophenylamine (656-65-5) + glycerol (56-81-5) → 6-bromo-7-fluoroquinoline (127827-52-5)

Conditions	Yield
With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 120 - 140℃;	85.8%
With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 110 - 140℃;	81%
Stage #1: 3-fluoro-4-bromophenylamine; glycerol With sulfuric acid; iron(II) sulfate In nitrobenzene at 130℃; for 14h; Stage #2: With ammonia; water In nitrobenzene at 20℃; pH=~ 8;	51.9%

3-fluoro-4-bromophenylamine (656-65-5) + 4-amino-6-chloro-pyrimidine-5-carbaldehyde (14160-93-1) → C11H8BrFN4O*ClH (1004956-71-1)

Conditions	Yield
With hydrogenchloride In acetonitrile at 70 - 75℃;	85%

methyl 3-cyclopropyl-3-oxopropanoate (32249-35-7) + 3-fluoro-4-bromophenylamine (656-65-5) + orthoformic acid triethyl ester (122-51-0) → methyl 3-(4-bromo-3-fluorophenylamino)-2-(cyclopropanecarbonyl)acrylate (1356953-34-8)

Conditions	Yield
at 140℃;	85%

cycl-isopropylidene malonate (2033-24-1) + 3-fluoro-4-bromophenylamine (656-65-5) + trimethyl orthoformate (149-73-5) → 5-(((4-bromo-3-fluorophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1581270-02-1)

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate at 100℃; for 1.5h; Stage #2: 3-fluoro-4-bromophenylamine In acetonitrile at 80 - 100℃; for 3.5h;	85%
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate at 100℃; for 1.5h; Stage #2: 3-fluoro-4-bromophenylamine at 80 - 100℃; for 3.5h;	71.3%
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate at 100℃; for 2h; Inert atmosphere; Stage #2: 3-fluoro-4-bromophenylamine at 100℃; Inert atmosphere;

3-fluoro-4-bromophenylamine (656-65-5) + 4-methyl-benzaldehyde (104-87-0) + acetophenone (98-86-2) → 3-(4-bromo-3-fluorophenylamino)-1-phenyl-3-ptolylpropan-1-one

Conditions	Yield
With 1-butyl-1,2,4-triazolium methanesulfonate In ethanol at 20℃; for 0.333333h; Reagent/catalyst; Mannich Aminomethylation;	85%

3-fluoro-4-bromophenylamine (656-65-5) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-[[(4-bromo-3-fluorophenyl)amino]methylidene]propanedioate (953803-86-6)

Conditions	Yield
In ethanol at 80℃; for 4h; Inert atmosphere;	84%
In ethanol at 80℃; for 4h; Inert atmosphere;	84%
In ethanol at 80℃; for 4h; Inert atmosphere;	84%

chloral ethyl hemiacetal (515-83-3) + 3-fluoro-4-bromophenylamine (656-65-5) → 5‐bromo‐6‐fluoro‐1H‐indole‐2,3‐dione (118897-99-7)

Conditions	Yield
Stage #1: chloral ethyl hemiacetal; 3-fluoro-4-bromophenylamine With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 55℃; for 20h; Stage #2: With sulfuric acid at 60 - 80℃; for 0.333333h;	83%
Stage #1: chloral ethyl hemiacetal; 3-fluoro-4-bromophenylamine With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 55℃; for 20h; Stage #2: With sulfuric acid at 60 - 80℃; for 0.333333h;	83%

3-fluoro-4-bromophenylamine (656-65-5) + isoquinoline 5-boronic acid (371766-08-4) → 3-fluoro-4-(isoquinolin-5-yl)benzenamine (1038867-89-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 110℃; for 4h;	82%

3-fluoro-4-bromophenylamine (656-65-5) → (4-bromo-3-fluorophenyl)hydrazine hydrochloride

Conditions	Yield
Stage #1: 3-fluoro-4-bromophenylamine With hydrogenchloride; sodium nitrite In water at -10℃; for 0.5h; Stage #2: With tin(II) chloride hydrate In water at 20℃; for 1h;	82%
Stage #1: 3-fluoro-4-bromophenylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 20℃; for 0.25h;	17%

tert-Butyl acrylate (1663-39-4) + 3-fluoro-4-bromophenylamine (656-65-5) → tert-butyl (2E)-3-(4-amino-2-fluorophenyl)prop-2-enoate (865138-40-5)

Conditions	Yield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 110℃; Heck reaction; Inert atmosphere;	80%

3-fluoro-4-bromophenylamine (656-65-5) + benzaldehyde (100-52-7) + acetophenone (98-86-2) → 3-(4-bromo-3-fluorophenylamino)-1,3-diphenylpropan-1-one

Conditions	Yield
With 1-butyl-1,2,4-triazolium methanesulfonate In ethanol at 20℃; for 0.333333h; Reagent/catalyst; Mannich Aminomethylation;	80%

3-fluoro-4-bromophenylamine (656-65-5) + 4-chlorobenzaldehyde (104-88-1) + acetophenone (98-86-2) → 3-(4-bromo-3-fluorophenylamino)-3-(4-chlorophenyl)-1-phenylpropan-1-one

Conditions	Yield
With 1-butyl-1,2,4-triazolium methanesulfonate In ethanol at 20℃; for 0.0833333h; Reagent/catalyst; Mannich Aminomethylation;	79%

Upstream product

• 64248-62-0 3,4-Difluorobenzonitrile 
• 133059-44-6 4-bromo-3-fluorobenzonitrile 
• 372-19-0 meta-fluoroaniline 
• 351-28-0 N-(3-fluorophenyl)acetamide 
• 351-30-4 N-(4-bromo-3-fluorophenyl)ethanamide 

Downstream Products

• 777-65-1 (E)-N-(4-bromo-3-fluorophenyl)-2-(oximido)acetamide 
• 3851-45-4 N-(4-bromo-3-fluoro-phenyl)-N'-phenyl-urea 
• 929279-27-6 N-(4-bromo-5-fluoro-2-nitrophenyl)-2,2,2-trifluoroacetamide 
• 879486-59-6 N-(4-bromo-3-fluoro-phenyl)-methanesulfonamide 
• 432049-39-3 diallyl-(4-bromo-3-fluorophenyl)amine 
• 1219741-79-3 4-bromo-5-fluoro-2-iodoaniline 
• 1001398-61-3 7-(4-bromo-3-fluorophenyl)-4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine 
• 1426805-60-8 N-(4-bromo-3-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)acetamide 
• 1426803-15-7 N-(4'-chloro-2-fluoro-2'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)-2-(4-(methylsulfonyl)phenyl)acetamide 
• 1351465-54-7 N-(4-bromo-3-fluorophenyl)-N'-(pyridin-4-ylcarbonyl)hydrazonoformamide 
• 956901-17-0 7-fluoroquinoline-6-carbonitrile 
• 1314787-88-6 3-fluoro-4-(2-methylpyridin-4-yl)aniline 
• 1185768-18-6 7-fluoroquinoline-6-carbaldehyde 
• 948883-08-7 5-azepan-1-yl-pentanoic acid (4-bromo-3-fluoro-phenyl)-amide 

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