130284-53-6

Basic information

• Product Name: 2-Chloro-3-bromo-5-aminopyridine
• Synonyms: 5-BROMO-6-CHLOROPYRIDIN-3-AMINE;5-AMINO-3-BROMO-2-CHLOROPYRIDINE;2-chloro-3-bromo-5-aminopyridine;5-BROMO-6-CHLORO-3-AMINOPYRIDINE;2-CHLORO-3-BROMO-5-AMINOPYRIDINE 98+%;3-Bromo-2-chloro-5-aminopyridine;2-chloro-3-bromopyridin-5-amine;5-bromo-6-chloropyridin-3-aminr
• CAS NO: 130284-53-6
• Molecular Formula: C₅H₄BrClN₂
• Molecular Weight: 207.46
• Product Categories: Pyridine;Pyridines;Boronic Acid
• Mol File: 130284-53-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 120-122°C
• Boiling Point: 336.729 °C at 760 mmHg
• Flash Point: 157.4 °C
• Appearance: /
• Density: 1.835 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: 2-8°C(protect from light)
• PKA: 0.86±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-3-bromo-5-aminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-bromo-5-aminopyridine(130284-53-6)
• EPA Substance Registry System: 2-Chloro-3-bromo-5-aminopyridine(130284-53-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-41
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 130284-53-6(Hazardous Substances Data)

Usage

General Description

2-Chloro-3-bromo-5-aminopyridine is an organic chemical compound with a molecular formula C5H4BrClN2. It is a heterocyclic aromatic compound that contains a pyridine ring with chlorine, bromine, and amino groups attached to it. 2-Chloro-3-bromo-5-aminopyridine is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and organic materials. It is a versatile intermediate in organic synthesis and is often used as a reagent in chemical reactions to introduce functional groups into organic molecules. 2-Chloro-3-bromo-5-aminopyridine is also known for its potential as a pharmaceutical intermediate, as it exhibits biological activity and is being researched for its potential use in the development of new drugs.

InChI:InChI=1/C5H4BrClN2/c6-4-1-3(8)2-9-5(4)7/h1-2H,8H2

Synthetic route

3-bromo-2-chloro-5-nitropyridine (5470-17-7) → 2-chloro-3-bromo-5-aminopyridine (130284-53-6)

Conditions	Yield
With hydrogen In tetrahydrofuran at 37℃; under 2250.23 Torr; for 18h; chemoselective reaction;	92%
With iron; acetic acid In water for 2h; below 50 deg C;	87%
With ammonium chloride; zinc In methanol at 90℃; for 2h;	70.6%

3-bromo-2-hydroxy-5-nitropyridine (15862-33-6) → 2-chloro-3-bromo-5-aminopyridine (130284-53-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / POCl3, quinoline / 2 h / 120 °C 2: 87 percent / Fe, AcOH / H2O / 2 h / below 50 deg C View Scheme

3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde (50675-18-8) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine (1378034-59-3)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 20h;	97%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 3-bromo-2-chloro-5-iodopyridine

Conditions	Yield
Stage #1: 5-amino-3-bromo-2-chloropyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Sandmeyer Reaction; Stage #2: In water at 0 - 20℃; Sandmeyer Reaction;	89%

tri-n-butyl(vinyl)tin (7486-35-3) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 6-chloro-5-vinylpyridin-3-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In 1,4-dioxane for 24h; Reflux;	89%

4-vinylpyridine (100-43-6) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine (552330-65-1)

Conditions	Yield
With triethylamine; tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 15h;	84%
With tris(dibenzylideneacetone)dipalladium (0); triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 15h;

4-vinylpyridine (100-43-6) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) + tris-(o-tolyl)phosphine (6163-58-2) → 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine (552330-65-1)

Conditions	Yield
With triethylamine; tris-(dibenzylideneacetone)dipalladium(0) In ethyl acetate; N,N-dimethyl-formamide	84%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + N-tert-butyloxycarbonyl-tryptophanal (82689-14-3) → 1,1-dimethylethyl [(1S)-2-[(5-bromo-6-chloro-3-pyridinyl)amino]-1-(1H-indol-3-ylmethyl)ethyl]carbamate (864773-87-5)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	75%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + Phe-COOH → N-(5-bromo-6-chloro-3-pyridinyl)-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalaninamide

Conditions	Yield
Stage #1: Phe-COOH With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 2h; Heating / reflux; Stage #2: 5-amino-3-bromo-2-chloropyridine In tetrahydrofuran for 1h; Heating / reflux;	59.4%

3-phenyl-propionaldehyde (104-53-0) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloro-N-(3-phenylpropyl)-3-pyridinamine (864773-02-4)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h;	50%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + acetic anhydride (108-24-7) → N-(5-bromo-6-chloropyridin-3-yl)acetamide

Conditions	Yield
at 20℃; for 1h;	49.5%

2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde (34941-21-4) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloro-N-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine (1378034-68-4)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 2h;	45.2%

5-methylfuran-2-boronic acid (62306-79-0) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 6-chloro-5-(5-methylfuran-2-yl)pyridin-3-amine

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In 1-methyl-pyrrolidin-2-one; water at 150℃; for 2h; Inert atmosphere;	22%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + acetic anhydride (108-24-7) → 5-bromo-6-chloropyridin-3-yl acetate (130284-55-8)

Conditions	Yield
With tetrafluoroboric acid; sodium nitrite 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h; Yield given. Multistep reaction;

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2-chloro-5-iodo-3-[(E)-2-pyridin-4-ylvinyl]pyridine (552330-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → (1R)-3-{6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1H-indol-3-ylmethyl)propylamine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h 3.1: 9-BBN / 0 - 20 °C 3.2: 40 percent / PdCl2(dppf); Cs2CO3 / dimethylformamide / 8 h / 50 °C 4.1: TFA / CH2Cl2 / 2 h / 20 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → N1-[6-chloro-5-(2-pyridin-4-yl-vinyl)-pyridin-3-yl]-3-(1H-indol-3-yl)-propane-1,2-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: acetic acid / methanol / 3 h / Heating 2.2: Ti(i-PrO)4; NaBH3CN / methanol / 1 h 3.1: TFA / CH2Cl2 / 2 h / 20 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → tert-butyl (1R)-3-{6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1H-indol-3-ylmethyl)propylcarbamate (552330-71-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h 3.1: 9-BBN / 0 - 20 °C 3.2: 40 percent / PdCl2(dppf); Cs2CO3 / dimethylformamide / 8 h / 50 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → [1-{[6-chloro-5-(2-pyridin-4-yl-vinyl)-pyridin-3-ylamino]-methyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (882170-52-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: acetic acid / methanol / 3 h / Heating 2.2: Ti(i-PrO)4; NaBH3CN / methanol / 1 h View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloropyridin-3-ol (130115-85-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) HBF4, NaNO2 / 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h 2: 98 percent / 2 N KOH / 0.5 h / 5 °C View Scheme
Stage #1: 5-amino-3-bromo-2-chloropyridine With sulfuric acid; sodium nitrite In water at 0 - 25℃; for 0.5h; Stage #2: With acetic acid In water at 100℃; for 12h;

1-azaadamantane-4-one (42949-24-6) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) + toluene-4-sulfonic acid (104-15-4) → (4s)-N-(5-bromo-6-chloropyridin-3-yl)-1-azatricyclo[3.3.1.13,7]decan-4-amine 4-methylbenzenesulfonate

Conditions	Yield
Stage #1: 1-azaadamantane-4-one; 5-amino-3-bromo-2-chloropyridine With magnesium sulfate; acetic acid for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 14h; Stage #3: toluene-4-sulfonic acid In ethanol; ethyl acetate at -10 - 20℃; Heating / reflux;

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → (6-chloro-pyridin-3-yl)-(tetrahydro-pyran-4-ylmethyl)-amine (1378034-61-7) + 2,5'-dichloro-2'-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridin-5-amine (1378034-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → N2'-(trans-4-aminocyclohexyl)-2,5'-dichloro-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N2'-(trans-4-(2-methoxyethylamino)cyclohexyl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 40 h / 20 - 120 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → trans-4-(2,5'-dichloro-5-((tetrahydro-2H-pyran-4-yl)methyl)amino-3,4'-bipyridin-2'-ylamino)cyclohexanol

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → trans-4-(2,5'-dichloro-5-((tetrahydro-2H-pyran-4-yl)methyl)amino-3,4'-bipyridin-2'-ylamino)cyclohexyl methanesulfonate

Conditions

Yield

Multi-step reaction with 5 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C 5: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N2'-(trans-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions

Yield

Multi-step reaction with 6 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C 5: triethylamine / dichloromethane / 2 h / 0 - 20 °C 6: tert-butyl alcohol / 5 h / 95 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N5-((tetrahydro-2H-pyran-4-yl)methyl)-N2'-(trans-4-(((R)-tetrahydrofuran-2-yl)methylamino)cyclohexyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: potassium carbonate / dimethyl sulfoxide / 9 h / 100 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N2'-(trans-4-(pyrrolidin-1-yl)cyclohexyl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N5-((tetrahydro-2H-pyran-4-yl)methyl)-N2'-(trans-4-((R)-3,3,3-trifluoro-2-methoxypropylamino)cyclohexyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dimethyl sulfoxide / 3 h / 135 °C View Scheme

Upstream product

• 5470-17-7 3-bromo-2-chloro-5-nitropyridine 
• 15862-33-6 3-bromo-2-hydroxy-5-nitropyridine 

Downstream Products

• 864773-02-4 5-bromo-6-chloro-N-(3-phenylpropyl)-3-pyridinamine 
• 1131041-71-8 5-bromo-6-chloro-2-nitropyridin-3-ol 
• 130115-85-4 5-bromo-6-chloropyridin-3-ol 
• 552330-65-1 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine 
• 130284-55-8 5-bromo-6-chloropyridin-3-yl acetate 
• 1361852-33-6 3-bromo-2-chloro-5-trifluoromethoxy-pyridine 

Relevant articles and documents

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