39856-58-1

Basic information

• Product Name: 3-Amino-2-bromopyridine
• Synonyms: 3-Amino-2-bromopyridine 97%;3-AMINO-2-BROMOPYRIDINE;2-BROMO-3-AMINOPYRIDINE;2-BROMOPYRIDINE-3-AMINE;2-BROMO-PYRIDINEAMINE;2-BROMO-PYRIDIN-3-YLAMINE;TIMTEC-BB SBB005539;2-Bromo-3-pyridinamine
• CAS NO: 39856-58-1
• Molecular Formula: C₅H₅BrN₂
• Molecular Weight: 173.01
• EINECS: -0
• Product Categories: Pyridine series;Amines;Pyridines;Pyridine;Bromopyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Amino-pyridine series
• Mol File: 39856-58-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 76-80 °C
• Boiling Point: 292.5 °C at 760 mmHg
• Flash Point: 130.7 °C
• Appearance: Beige to dark brown/Crystalline Powder
• Density: 1.71 g/cm³
• Vapor Pressure: 0.00182mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: Room temperature.
• PKA: 1.72±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 109830
• CAS DataBase Reference: 3-Amino-2-bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-2-bromopyridine(39856-58-1)
• EPA Substance Registry System: 3-Amino-2-bromopyridine(39856-58-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36/39-37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 39856-58-1(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Cryst

Uses

Used in a palladium-catalyzed synthesis of indole systems containing fused medium- and large-ring heterocycles. pyrrole derivatives ahs been prepared using 3-Amino-2-bromopyridine. Used in P-C coupling reaction.

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

Synthetic route

2-bromo-3-nitropyridine (19755-53-4) → 3-amino-2-bromopyridine (39856-58-1)

Conditions	Yield
With iron; ammonium chloride In tetrahydrofuran; water at 60 - 70℃; for 5h;	100%
With aluminum (III) chloride; iron In tetrahydrofuran; water	100%
With iron; acetic acid for 2h; Heating;	66%
With iron; acetic acid at 100℃;
With iron In acetic acid

2-bromonicotinamide (87674-18-8) → 3-amino-2-bromopyridine (39856-58-1)

Conditions	Yield
With sodium hydroxide; bromine In water 1) 0.5 hr, rt; 2) 3hr, 80 deg C;	75%

pyridin-3-ylamine (462-08-8) → 6-bromopyridine-3-amine (13534-97-9) + 3-amino-2-bromopyridine (39856-58-1) + 2,6-dibromo-3-aminopyridine (39856-57-0)

Conditions	Yield
With N-Bromosuccinimide In methanol at 20℃; for 144h;	A 6 % Spectr. B 43% C 20 % Spectr.
With N-Bromosuccinimide In acetonitrile at 20℃; for 24h;	A 32 % Spectr. B 40 % Spectr. C 14 % Spectr.

pyridin-3-ylamine (462-08-8) → 3-amino-2-bromopyridine (39856-58-1)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 20h;	12%
With D-glucose; Escherichia coli flavin reductase; Bacillus megaterium glucose dehydrogenase; Lechevalieria aerocolonigenes tryptophan-7-halogenase; flavin adenine dinucleotide; NADH In aq. phosphate buffer; isopropyl alcohol pH=7.4; Enzymatic reaction;

2-amino-3-nitropyridine (4214-75-9) → 3-amino-2-bromopyridine (39856-58-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: HBr 47 percent; NaNO2 1.2: CuBr 2.1: Fe / acetic acid View Scheme

2-hydroxy-3-nitropyridine (6332-56-5) → 3-amino-2-bromopyridine (39856-58-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; phosphorus (III)-bromide / 100 °C 2: iron-turnings; acetic acid / 100 °C View Scheme

pyridin-3-ylamine (462-08-8) + N-bromo-succinimide (NBS) → 3-amino-2-bromopyridine (39856-58-1)

Conditions	Yield
In trifluoroacetic acid

3-amino-2-bromopyridine (39856-58-1) + iodobenzene (591-50-4) → 2-bromo-N-phenylpyridin-3-amine

Conditions	Yield
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 6h; Sealed tube;	99%
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 110℃; for 6h; Sealed tube;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 17h; Cross-coupling;	64%
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 14h;	36.6%
Stage #1: 3-amino-2-bromopyridine With copper(l) iodide; palladium 10% on activated carbon; caesium carbonate; triphenylphosphine at 20℃; for 0.25h; Inert atmosphere; Stage #2: iodobenzene at 95 - 100℃; for 2.5h; Inert atmosphere;

3-amino-2-bromopyridine (39856-58-1) + tert-butyl [(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}but-3-yn-2-yl]carbamate (1374041-14-1) → tert-butyl [(2S)-4-(3-aminopyridin-2-yl)-1-{[tert-butyl(diphenyI)silyl]oxy}but-3-yn-2-yl]carbamate (1374041-15-2)

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine; tert-butyl [(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}but-3-yn-2-yl]carbamate With triethylamine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 20℃; for 0.0833333h; Stage #2: With copper(l) iodide In acetonitrile at 52℃; for 4.5h; Inert atmosphere;	99%

3-amino-2-bromopyridine (39856-58-1) + (S)-(2-(1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)pyridin-4-yl)boronic acid trifluoroacetic acid → (S)-tert-butyl (1-(3-amino-[2,4‘-bipyridin]-2‘-yl)but-3-en-1yl)carbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 120℃; for 0.5h; Inert atmosphere;	99%

3-amino-2-bromopyridine (39856-58-1) + 2-methyl-1,3-oxazole-4-carboxylic acid chloride (62348-22-5) → N-(2-bromopyridin-3-yl)-2-methyl-1,3-oxazole-4-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 40℃; for 18h; Inert atmosphere;	98%

3-amino-2-bromopyridine (39856-58-1) + potassium ethyl xanthogenate (140-89-6) → 2-mercaptothiazolo[5,4-b]pyridine (57135-09-8)

Conditions	Yield
In N,N-dimethyl-formamide at 130℃;	97%

3-amino-2-bromopyridine (39856-58-1) + 4-chlorobenzoyl chloride (586-75-4) → 4-bromo-N-(2-bromopyridin-3-yl)benzamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	97%

3-amino-2-bromopyridine (39856-58-1) + tert.-butylnitrite (540-80-7) + 2,2,2-trifluoroethanol (75-89-8) → 2-bromo-3-(2,2,2-trifluoroethoxy)pyridine

Conditions	Yield
With methanesulfonic acid	96%

3-amino-2-bromopyridine (39856-58-1) → 3-amino-2-iodopyridine

Conditions	Yield
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In 1,4-dioxane at 110℃; for 24h;	94%

3-amino-2-bromopyridine (39856-58-1) + 2-phenyl-1,3-oxazole-4-carbonyl chloride (1204-70-2) → N-(2-bromopyridin-3-yl)-2-phenyl-1,3-oxazole-4-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 40℃; for 18h; Inert atmosphere;	94%

3-amino-2-bromopyridine (39856-58-1) + 4-chloro-2-ethynyl-1-fluorobenzene (657425-07-5) → 2-((5-chloro-2-fluorophenyl)ethynyl)pyridin-3-amine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 110℃; for 1h; Inert atmosphere;	94%

3-amino-2-bromopyridine (39856-58-1) + pivaloyl chloride (3282-30-2) → N-(2-bromopyridin-3-yl)trimethylacetamide (835882-02-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	93%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	93%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	90%

3-amino-2-bromopyridine (39856-58-1) + formic acid ethyl ester (109-94-4) → N-(2-bromopyridin-3-yl)formamide (1160653-52-0)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 24h;	91%

3-amino-2-bromopyridine (39856-58-1) + quinoline-2-carboxylic acid (93-10-7) → N-(2-bromo-3-pyridyl)quinoline-2-carboxamide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h;	91%

3-amino-2-bromopyridine (39856-58-1) + 3-pyridylboronic acid (1692-25-7) → 2-bromo-3,3'-bipyridine (101002-03-3)

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 20h; Suzuki Coupling; Inert atmosphere;	90%

pyridine-4-carbonitrile (100-48-1) + 3-amino-2-bromopyridine (39856-58-1) → C11H9BrN4 (1505566-25-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	90%

3-amino-2-bromopyridine (39856-58-1) + allyl bromide (106-95-6) → 2-bromo-3-(N,N-diallylamino)pyridine (1013629-47-4)

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at -78℃; Inert atmosphere;	87%

3-amino-2-bromopyridine (39856-58-1) + diisopropyl hydrogenphosphonate (1809-20-7) → diisopropyl 3-aminopyridin-2-ylphosphonate

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 115℃; for 24h; Solvent; Inert atmosphere;	87%

3-amino-2-bromopyridine (39856-58-1) + 4,5-dichloro-1,2,3-dithiazolium chloride (75318-43-3) → (Z)-2-bromo-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-3-amine

Conditions	Yield
With pyridine In dichloromethane at 20℃; Inert atmosphere;	87%

3-amino-2-bromopyridine (39856-58-1) + benzoyl chloride (98-88-4) → N-(2-bromopyridin-3-yl)benzamide (942220-36-2)

Conditions	Yield
With pyridine In dichloromethane at 0 - 25℃; for 16h;	86%
With pyridine at -10 - 20℃;	74%
With dmap; triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
for 3h;	161 mg

3-amino-2-bromopyridine (39856-58-1) + methyl iodide (74-88-4) → N-(2-bromopyridin-3-yl)-N-methylamine (872492-60-9)

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃;	85%

3-amino-2-bromopyridine (39856-58-1) + methyl 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate (125097-83-8) → tert-butyl 3-[(2-bromo-3-pyridyl)carbamoyl]-1,2,5,6-tetrahydropyridine-1-carboxylate (320774-02-5)

Conditions	Yield
With trimethylaluminum In dichloromethane at 0℃; Heating / reflux;	85%

3-amino-2-bromopyridine (39856-58-1) + trans-2-phenylvinylboronic acid (6783-05-7) → (E)-2-styrylpyridin-3-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 16h; Suzuki Coupling; Inert atmosphere;	85%

3-amino-2-bromopyridine (39856-58-1) + 4-bromo-1,2-dihydronaphthalene (3333-24-2) → 6,11-dihydro-5H-benzo[g]pyrido[3,2-b]indole (25726-64-1)

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; XPhos In tert-butyl alcohol at 110℃; for 24h; Sealed tube; Inert atmosphere;	85%

3-amino-2-bromopyridine (39856-58-1) + 4-tert-Butylphenylacetylene (772-38-3) → 2-(4-(tert-butyl)phenyl)-1H-pyrrolo[3,2-b]pyridine

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine; 4-tert-Butylphenylacetylene With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; di(1-adamantyl)benzylphosphonium hydrobromide In dimethyl sulfoxide at 100℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 0.25h; Schlenk technique; Inert atmosphere;	85%

3-amino-2-bromopyridine (39856-58-1) + 1-isocyanato-4-trifluoromethoxy-benzene (35037-73-1) → 1-(2-bromopyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea (917966-91-7)

Conditions	Yield
In tetrahydrofuran at 23℃; for 16h;	84%

3-amino-2-bromopyridine (39856-58-1) + phenylboronic acid (98-80-6) → 3-amino-2-phenylpyridine (101601-80-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 95℃; for 16h; Sealed tube;	84%
With potassium phosphate; tetrabutylammomium bromide In water at 85℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;	82%
Suzuki Coupling;

3-amino-2-bromopyridine (39856-58-1) + {3-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]phenyl}boronic acid → tert-butyl N-[(1S)-1-[3-(3-aminopyridin-2-yl)phenyl]but-3-en-1yl]carbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	84%
With tetrakis(triphenylphosphine) palladium(0); sodium sulfate In 1,4-dioxane at 120℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	84%
With tetrakis(triphenylphosphine) palladium(0)

3-amino-2-bromopyridine (39856-58-1) + C16H19NO2 → C21H23N3O2

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere;	84%

3-amino-2-bromopyridine (39856-58-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-(3-bromo-2-pyridyl)-carbamate (149489-04-3)

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine With sodium hexamethyldisilazane In tetrahydrofuran for 0.166667h; Inert atmosphere; Cooling; Large scale; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 15℃; for 1h; Inert atmosphere; Large scale;	84%

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 6332-56-5 2-hydroxy-3-nitropyridine 
• 4214-75-9 2-amino-3-nitropyridine 
• 87674-18-8 2-bromonicotinamide 
• 19755-53-4 2-bromo-3-nitropyridine 

Downstream Products

• 872492-60-9 N-(2-bromopyridin-3-yl)-N-methylamine 
• 452972-08-6 2-bromo-3-pyridylboronic acid 
• 452972-12-2 2-[3-(2-bromo)pyridine]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 10261-82-2 1,5-naphthyridin-2(1H)-one 
• 272-49-1 1H-pyrrolo[3,2-b]pyridine 
• 1158807-07-8 2-(2-(methylthio)phenyl)pyridin-3-amine 
• 116026-98-3 (2-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester 
• 209798-50-5 (E)-2-styrylpyridin-3-amine 
• 1260163-30-1 N-[2-(3-chlorophenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1402939-26-7 2-phenyl-3-p-tolylpyrido[3,2-d]pyrimidin-4(3H)-one 
• 1402939-12-1 (Z)-methyl N-2-bromopyridin-3-ylbenzimidate 
• 1374041-15-2 tert-butyl [(2S)-4-(3-aminopyridin-2-yl)-1-{[tert-butyl(diphenyI)silyl]oxy}but-3-yn-2-yl]carbamate 
• 1366542-58-6 2-bromo-N-(4-methoxycyclohexyl)pyridin-3-amine 
• 1366542-62-2 2-bromo-N-(4-methoxycyclohexyl)pyridin-3-amine 

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