7598-35-8

Basic information

• Product Name: 4-Amino-2-bromopyridine
• Synonyms: 2-bromo-4-pyridinamin;IFLAB-BB F1371-0175;AKOS BBS-00001327;4-PYRIDINAMINE, 2-BROMO-;4-AMINO-2-BROMOPYRIDINE;2-BROMOPYRIDIN-4-AMINE;2-BROMO-PYRIDIN-4-YLAMINE;2-BROMO-4-PYRIDINAMINE
• CAS NO: 7598-35-8
• Molecular Formula: C₅H₅BrN₂
• Molecular Weight: 173.01
• EINECS: -0
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Amines;Pyridines;Pyridines derivates
• Mol File: 7598-35-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 92-96 °C
• Boiling Point: 321.3 °C at 760 mmHg
• Flash Point: 148.1 °C
• Appearance: White to pale brown to orange/Crystalline Powder or Powder
• Density: 1.71 g/cm³
• Vapor Pressure: 0.000301mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.89±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 108928
• CAS DataBase Reference: 4-Amino-2-bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2-bromopyridine(7598-35-8)
• EPA Substance Registry System: 4-Amino-2-bromopyridine(7598-35-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36/37/38-36-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7598-35-8(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Cryst

Uses

4-Amino-2-bromopyridine is used as medical intermediate.

InChI:InChI=1/C5H5BrN2/c6-5-3-4(7)1-2-8-5/h1-3H,(H2,7,8)

Synthetic route

2-bromo-4-nitropyridine N-oxide (52092-43-0) → 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
With iron In acetic acid at 100℃;	100%
With iron In acetic acid	90%
With iron; acetic acid

2-bromo-4-nitropyridine (6945-67-1) → 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
With titanium for 0.25h;	97%

4-aminopyridine (504-24-5) → 2-bromo-4-aminopyridine (7598-35-8) + 4-amino-3,5-dibromopyridine (84539-34-4)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 48h; Darkness;	A n/a B 55%

2,4-dibromopyridine (58530-53-3) → 2-amino-4-bromopyridine (84249-14-9) + 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
With ammonium hydroxide at 160℃;

2,4-dibromopyridine (58530-53-3) + ammonium hydroxide → 2-amino-4-bromopyridine (84249-14-9) + 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
at 160℃;

2-bromo-pyridine (109-04-6) + (+-)-2-<4-chloro-phenyl>-5-piperidino-valeronitrile → 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: perbenzoic acid / CHCl3 / 72 h / Ambient temperature 2: 77 percent / 96percent H2SO4, 96percent HNO3 / 3 h / 130 °C 3: 90 percent / iron powder / acetic acid View Scheme

2-bromopyridine-N-oxide (14305-17-0) → 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / 96percent H2SO4, 96percent HNO3 / 3 h / 130 °C 2: 90 percent / iron powder / acetic acid View Scheme
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid 2: iron-powder; acetic acid View Scheme
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid 2: FeSO4; concentrated aqueous NH3 View Scheme

3-deazauracil (626-03-9) → 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl bromide / 130 °C 2: aqueous NH3 / 160 °C View Scheme

2-bromo-4-nitropyridine N-oxide (52092-43-0) + iron (7439-89-6) → 2-bromo-4-aminopyridine (7598-35-8)

Conditions	Yield
In acetic acid
With ammonium chloride In ethanol

2-bromo-4-aminopyridine (7598-35-8) + phenylboronic acid (98-80-6) → 2-phenyl-pyridin-4-ylamine (21203-86-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; carbon dioxide In water; acetonitrile at 70℃; under 23257.6 Torr; for 24h; Reagent/catalyst; Pressure; Suzuki Coupling; Inert atmosphere;	99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 110℃; Sealed tube;	61.8%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water Suzuki Coupling; Reflux; Inert atmosphere;	44%

2-bromo-4-aminopyridine (7598-35-8) + 2,5-hexanedione (110-13-4) → 2-bromo-4-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (956384-89-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 2h; Heating;	86%

2-bromo-4-aminopyridine (7598-35-8) + 4-fluoro-3-nitro-benzoic acid methyl ester (329-59-9) → 4-(2-bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester (1227380-68-8)

Conditions	Yield
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 4-fluoro-3-nitro-benzoic acid methyl ester In tetrahydrofuran; mineral oil at 20℃;	85%
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 4-fluoro-3-nitro-benzoic acid methyl ester In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	85%
Stage #1: 4-fluoro-3-nitro-benzoic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 2-bromo-4-aminopyridine In tetrahydrofuran at 0 - 20℃;	85%

2-bromo-4-aminopyridine (7598-35-8) + 2-(5-fluoro-6-methylpyridin-2-yl)-9-(4-methoxybenzyl)-6-phenoxy-9H-purine → N-(2-bromopyridin-4-yl)-2-(5-fluoro-6-methylpyridin-2-yl)-9-(4-methoxybenzyl)-9H-purin-6-amine

Conditions	Yield
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 2-(5-fluoro-6-methylpyridin-2-yl)-9-(4-methoxybenzyl)-6-phenoxy-9H-purine In N,N-dimethyl-formamide at 20℃; for 3h;	85%

2-bromo-4-aminopyridine (7598-35-8) + di-tert-butyl dicarbonate (24424-99-5) → 2-bromo-4-[(tert-butoxycarbonyl)amino]pyridine (433711-95-6)

Conditions	Yield
With triethylamine In dichloromethane at 50℃; for 16h; Inert atmosphere;	84%
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 25℃; Inert atmosphere;	74%
With triethylamine In tetrahydrofuran at 0 - 25℃;	72%
With triethylamine In dichloromethane
Stage #1: 2-bromo-4-aminopyridine With triethylamine In dichloromethane at 20 - 30℃; Stage #2: di-tert-butyl dicarbonate With dmap In dichloromethane at 20 - 30℃; for 16h;	171.2 g

2-bromo-4-aminopyridine (7598-35-8) + 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8) → 1,3-bis(4-amino-2-pyridyl)benzene (1369963-51-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 48h; Inert atmosphere; Reflux;	84%

2-bromo-4-aminopyridine (7598-35-8) + ethyl iodide (75-03-6) → 2-bromo-N,N-diethylpyridine-4-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Reflux;	81.8%

2-bromo-4-aminopyridine (7598-35-8) → 2-Brom-4-(nitroamino)pyridin (15367-12-1)

Conditions	Yield
With sulfuric acid; nitric acid at -10 - -5℃;	79%
With sulfuric acid; nitric acid at 0℃; for 0.333333h;

2-bromo-4-aminopyridine (7598-35-8) + 2,6-dichloro-3,5-dinitrotoluene (51676-76-7) → 2-bromo-N-(3-chloro-2-methyl-4,6-dinitrophenyl)pyridin-4-amine

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide at 25℃;	79%

2-bromo-4-aminopyridine (7598-35-8) + C10H4Cl2F3N3O → 1-(3-chloropyridin-2-yl)-N-(2-bromopyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 12h;	78%

2-bromo-4-aminopyridine (7598-35-8) + chloroacetyl chloride (79-04-9) → N-(2-bromopyridin-4-yl)-2-chloroacetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h;	76.5%

2-bromo-4-aminopyridine (7598-35-8) → 2-ethoxy-pyridin-4-ylamine (89943-12-4)

Conditions	Yield
With sodium hydroxide In ethanol; water	76%
With sodium ethanolate at 160℃;

2-bromo-4-aminopyridine (7598-35-8) + 3-pyridylboronic acid (1692-25-7) → [2,3']bipyridinyl-4-ylamine (40963-62-0)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 110℃; for 24h; Suzuki Coupling; Inert atmosphere;	76%

2-bromo-4-aminopyridine (7598-35-8) + 1-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-4-isopropylpiperazine → 2-(2-fluoro-4-((4-isopropylpiperazin-1-yl)methyl)phenyl)pyridin-4-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 2-methyltetrahydrofuran; water at 25 - 73℃; for 16h; Inert atmosphere; Large scale;	76%

1-methyl-piperazine (109-01-3) + 2-bromo-4-aminopyridine (7598-35-8) → 2-(4-methylpiperazin-1-yl)pyridin-4-ylamine (876343-33-8)

Conditions	Yield
at 135℃; for 16h; Sealed tube;	75.7%

2-bromo-4-aminopyridine (7598-35-8) + di-tert-butyl dicarbonate (24424-99-5) → 2-bromo-N,N-(di-tert butoxycarbonyl)pyridine-4-amine (1044148-89-1)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20 - 80℃; for 24h;	75.2%
With sodium hexamethyldisilazane In tetrahydrofuran

2-bromo-4-aminopyridine (7598-35-8) + 2,6-Dichlorobenzoyl chloride (4659-45-4) → N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (1258298-00-8)

Conditions	Yield
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Stage #2: 2,6-Dichlorobenzoyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 4h;	74%
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2,6-Dichlorobenzoyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 4h;	54%
With sodium hydride In N,N-dimethyl-formamide at 0℃;
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 2,6-Dichlorobenzoyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;

2-bromo-4-aminopyridine (7598-35-8) + 9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-6-phenoxy-9H-purine → N-(2-bromopyridin-4-yl)-9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-9H-purin-6-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 3h;	71.5%

2-bromo-4-aminopyridine (7598-35-8) + 2,6-dichloro-4-cyanobenzoyl chloride (1258298-06-4) → N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (1258298-07-5)

Conditions	Yield
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Stage #2: 2,6-dichloro-4-cyanobenzoyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	70%
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 2,6-dichloro-4-cyanobenzoyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere;	59%

2-bromo-4-aminopyridine (7598-35-8) + 2-(3,5-bis-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (69807-91-6) → 4-amino-2-(3,5-bis(trifluoromethyl)phenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; methanol; water at 100℃; for 3h; Microwave irradiation;	70%

2-bromo-4-aminopyridine (7598-35-8) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → N-(2-bromopyridin-4-yl)-2,4,6-trichlorobenzamide (1258298-03-1)

Conditions	Yield
Stage #1: 2-bromo-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Stage #2: 2,4,6-trichlorobenzoyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	69%

2-Hydroxymethylpyridine (586-98-1) + 2-bromo-4-aminopyridine (7598-35-8) → N-(pyridine-2-methyl)-4-amino-2-bromopyridine (1439400-79-9)

Conditions	Yield
With (phthalocyaninato)iron(II); sodium t-butanolate In toluene at 100℃; for 12h; Inert atmosphere;	68%

2-bromo-4-aminopyridine (7598-35-8) + propionyl chloride (79-03-8) → N-(2-bromopyridin-4-yl)propanamide

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 2h;	67%

2-bromo-4-aminopyridine (7598-35-8) + 2,2,2-trifluoroethanol (75-89-8) → 2-(2,2,2-trifluoroethoxy)pyridin-4-amine (1247075-58-6)

Conditions	Yield
With sodium hydride In 1,4-dioxane for 15h; Reflux;	66.2%

2-bromo-4-aminopyridine (7598-35-8) + 4,4,5,5-tetramethyl-2-(2,4-bis(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1073353-65-7) → 4-amino-2-(2,4-bis(trifluoromethyl)phenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; methanol; water at 100℃; for 3h; Microwave irradiation;	65%

2-bromo-4-aminopyridine (7598-35-8) + (2,6-difluoropyridin-3-yl)boronic acid (136466-94-9) → 2',6'-difluoro-4-amino-2,3'-bipyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; for 18h; Inert atmosphere;	63%

2-bromo-4-aminopyridine (7598-35-8) + Nitrosobenzene (586-96-9) → 2-bromo-(4-phenylazo)pyridine

Conditions	Yield
With pyridine; trimethylphenylammonium hydroxide at 80℃; for 4h;	61%

2-bromo-4-aminopyridine (7598-35-8) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite	60%
With sulfuric acid; copper(II) sulfate; potassium bromide; sodium nitrite Diazotization.Reagens 4: Kupfer-Pulver; Reagens 5: Wasser;

Upstream product

• 58530-53-3 2,4-dibromopyridine 
• 6945-67-1 2-bromo-4-nitropyridine 
• 504-24-5 4-aminopyridine 
• 52092-43-0 2-bromo-4-nitropyridine N-oxide 
• 7439-89-6 iron 
• 626-03-9 3-deazauracil 
• 14305-17-0 2-bromopyridine-N-oxide 
• 109-04-6 2-bromo-pyridine 

Downstream Products

• 10386-27-3 2-bromoisonicotinonitrile 
• 58530-53-3 2,4-dibromopyridine 
• 89943-12-4 4-Amino-2-ethoxy-pyridin 
• 861023-90-7 2,3-dibromopyridin-4-amine 
• 861024-31-9 2,3,5-tribromo-[4]pyridylamine 
• 433711-95-6 2-bromo-4-[(tert-butoxycarbonyl)amino]pyridine 
• 357927-50-5 2-bromo-4-fluoro-pyridine 
• 876343-33-8 2-(4-methylpiperazin-1-yl)pyridin-4-ylamine 
• 35980-77-9 2-morpholinopyridine-4-amine 
• 1578484-42-0 7-bromo-2-chloro-1,6-naphthyridine 
• 847799-64-8 2-bromo-N-methylpyridine-4-amine 

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