139585-70-9

Basic information

• Product Name: 2-Bromo-5-cyanopyridine
• Synonyms: 6-BroMonicotinitrile;2-Bromo-5-cyanopyridine≥ 98.5% (HPLC);5-Cyano-2-bromopyridine;3-PYRIDINECARBONITRILE, 6-BROMO-;6-BROMO-NICOTINONITRILE;2-BROMO-5-CYANOPYRIDINE;6-Bromo-3-cynopyridine;2-Bromo-5-cyanopyridine 97%
• CAS NO: 139585-70-9
• Molecular Formula: C₆H₃BrN₂
• Molecular Weight: 183.01
• EINECS: -0
• Product Categories: Benzothiazoles;blocks;Bromides;Carboxes;Pyridines;Pyridine;Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;Pyridine series;Halides
• Mol File: 139585-70-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 136-140
• Boiling Point: 261.642 °C at 760 mmHg
• Flash Point: 112.037 °C
• Appearance: /Solid
• Density: 1.72 g/cm³
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Keep Cold
• PKA: -2.66±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-5-cyanopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-cyanopyridine(139585-70-9)
• EPA Substance Registry System: 2-Bromo-5-cyanopyridine(139585-70-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39-24/25
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 139585-70-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 66, p. 1500, 2001 DOI: 10.1021/jo005682n

InChI:InChI=1/C6H3BrN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H

Synthetic route

6-chloronicotinonitrile (33252-28-7) → 2-bromo-5-cyanopyridine (139585-70-9)

Conditions	Yield
With phosphorus tribromide at 145℃; for 64h;	81%
Stage #1: 6-chloronicotinonitrile With phosphorus tribromide at 145℃; for 64h; Stage #2: With sodium hydrogencarbonate In water	81%
With phosphorus tribromide at 145℃; for 64h;	61%

zinc(II) cyanide (557-21-1) + 6-bromopyridin-3-ylboronic acid (223463-14-7) → 2-bromo-5-cyanopyridine (139585-70-9)

Conditions	Yield
With copper(II) nitrate trihydrate; cesium fluoride In methanol; water at 80℃; for 2h;	61%

6-bromonicotinaldehyde (149806-06-4) → 2-bromo-5-cyanopyridine (139585-70-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; potassium carbonate / 20 °C 2: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C View Scheme

C6H5BrN2O (864266-28-4) → 2-bromo-5-cyanopyridine (139585-70-9)

Conditions	Yield
With fluorosulfonyl fluoride; potassium carbonate at 20℃; for 12h;	340 mg

2-bromo-5-(hydroxymethyl)pyridine (122306-01-8) → 2-bromo-5-cyanopyridine (139585-70-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; fluorosulfonyl fluoride; dimethyl sulfoxide / 20 °C 2: hydroxylamine hydrochloride; potassium carbonate / 20 °C 3: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C View Scheme

potassium vinyltrifluoroborate + 2-bromo-5-cyanopyridine (139585-70-9) → 6-ethenylpyridine-3-carbonitrile (16173-99-2)

Conditions	Yield
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In methanol at 20 - 80℃; for 8h; Product distribution / selectivity; Sealed tube;	99%
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In methanol at 80℃; for 8h; Sealed tube;	99%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In ethanol; water at 90℃; Suzuki Coupling;	98%

1-methyl-1H-imidazole (616-47-7) + 2-bromo-5-cyanopyridine (139585-70-9) → 1,3-bis(5-cyanopyridin-2-yl)-1H-imidazolium bromide

Conditions	Yield
In neat (no solvent) at 190℃; for 18h; Sealed tube;	98%
at 190℃; for 18h;	73%
at 20 - 190℃; for 18h; Inert atmosphere;	70%
In neat (no solvent) at 190℃; for 18h; Sealed tube;

[4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)phenyl]boronic acid + 2-bromo-5-cyanopyridine (139585-70-9) → C27H21N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; potassium carbonate In toluene at 100℃; Inert atmosphere;	98%

S-Methylisothiourea sulfate (867-44-7) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-(methylthio)nicotinonitrile (408350-80-1)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 1h;	98%

6-bromo-4-(((3S,4S)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide + 2-bromo-5-cyanopyridine (139585-70-9) → 6-bromo-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (1400580-92-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1.5h; Sealed tube;	97%

8-quinolinol (148-24-3) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-(quinolin-8-yloxy)nicotinonitrile (1042780-34-6)

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere;	96%

tert-butyl 4-iodopiperidine-1-carboxylate (301673-14-3) + 2-bromo-5-cyanopyridine (139585-70-9) → tert-butyl 4-(5-cyanopyridin-2-yl)piperidine-1-carboxylate (912556-76-4)

Conditions	Yield
Stage #1: tert-butyl 4-iodopiperidine-1-carboxylate With zinc In tetrahydrofuran at 65℃; for 0.5h; Stage #2: 2-bromo-5-cyanopyridine With N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide at 65℃; for 18h;	96%

n-butyllithium (109-72-8, 29786-93-4) + Triisopropyl borate (5419-55-6) + 2-bromo-5-cyanopyridine (139585-70-9) → lithium triisopropyl 2-(5-cyanopyridyl) borate

Conditions	Yield
In tetrahydrofuran; toluene 1. triisopropylborate, toluene/THF 4/1; 2. n-C4H9Li over 90 min, -78°C to room temp.;	95%

cyclopropanemethylamine (2516-47-4) + 2-bromo-5-cyanopyridine (139585-70-9) → C10H11N3 (1016819-90-1)

Conditions	Yield
In 1,4-dioxane at 100℃; for 16h; Sealed tube;	95%

(S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (101469-92-5) + 2-bromo-5-cyanopyridine (139585-70-9) → tert-butyl (S)-3-((5-cyanopyridin-2-yl)oxy)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 0.5h; Inert atmosphere; Stage #2: 2-bromo-5-cyanopyridine In N,N-dimethyl-formamide at 0 - 25℃; for 2h; Inert atmosphere;	94%

Cyclopentamine (1003-03-8) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-(cyclopentylamino)nicotinonitrile (566160-30-3)

Conditions	Yield
In 1,4-dioxane at 100℃; for 16h; Sealed tube;	93%

2-bromo-5-cyanopyridine (139585-70-9) + tributyl(4-hexyl-2-thienyl)stannane → 6-(4-hexylthiophen-2-yl)nicotinonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 8h; Stille Cross Coupling; Inert atmosphere;	93%

S-tert-butylsulfinimide (146374-27-8) + 2-bromo-5-cyanopyridine (139585-70-9) → N-(5-cyanopyridin-2-yl)-2-methylpropane-2-sulfinamide (1338209-77-0)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;	92%

2-bromo-5-cyanopyridine (139585-70-9) → 6-bromopyridine-3-carboxamide (889676-37-3)

Conditions	Yield
With sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; ethanol for 4h; Reflux;	92%

2-bromo-5-cyanopyridine (139585-70-9) + trimethylsilylacetylene (1066-54-2) → 6-[(trimethylsilyl)ethynyl] pyridine-3-carbonitrile (1214278-89-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 24h; Sonogashira coupling; Inert atmosphere;	91%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 12h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran Sonogashira Cross-Coupling; Inert atmosphere;

2-bromo-5-cyanopyridine (139585-70-9) → 2,2’-bipyridine-5,5’-dicarbonitrile (1802-29-5)

Conditions	Yield
Stage #1: 2-bromo-5-cyanopyridine With nickel(II) chloride hexahydrate; lithium chloride; zinc In N,N-dimethyl-formamide at 40℃; Stage #2: With iodine; acetic acid In N,N-dimethyl-formamide at 50℃; for 0.5h; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide at 0℃; for 0.5h;	91%
With nickel(II) chloride hexahydrate; iodine; acetic acid; lithium chloride; zinc In N,N-dimethyl-formamide at 40 - 50℃; for 0.5h;	91%
With nickel(II) chloride hexahydrate; iodine; acetic acid; lithium chloride; zinc In N,N-dimethyl-formamide at 50 - 60℃; for 6h;	90%

tert-butylmagnesium chloride (677-22-5) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-tert-butylpyridine-3-carbonitrile (56029-45-9)

Conditions	Yield
With copper(l) iodide; lithium bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	91%

2-bromo-5-cyanopyridine (139585-70-9) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → N,N-diphenyl-4-(5-cyanopyridin-2-yl)aniline (1422183-11-6)

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.5h; Suzuki Coupling;	90%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;	70%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 1h; Suzuki Coupling;

2-bromo-5-cyanopyridine (139585-70-9) + (6-fluoropyridin-3-yl)boronic acid (351019-18-6) → 6'-fluoro-2,3'-bipyridine-5-carbonitrile (1445207-23-7)

Conditions	Yield
With potassium phosphate; palladium diacetate; catacxium A In tetrahydrofuran; water at 60℃; for 0.5h;	90%

2,4-difluorophenylboronic acid (144025-03-6) + 2-bromo-5-cyanopyridine (139585-70-9) → 2-(2,4-difluorophenyl)pyridine-5-nitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 24h; Reflux;	89%

2,4-difluorophenylboronic acid (144025-03-6) + 2-bromo-5-cyanopyridine (139585-70-9) → 2-(2',4'-difluorophenyl)-5-amidopyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate In ethanol; toluene for 24h; Reflux;	89%

Ethyl bromodifluoroacetate (667-27-6) + 2-bromo-5-cyanopyridine (139585-70-9) → ethyl 2-(5-cyanopyridin-2-yl)-2,2-difluoroacetate

Conditions	Yield
Stage #1: Ethyl bromodifluoroacetate With copper In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-bromo-5-cyanopyridine In dimethyl sulfoxide at 20℃; for 12h;	89%
Stage #1: Ethyl bromodifluoroacetate With copper In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-bromo-5-cyanopyridine In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere;	86%
Stage #1: Ethyl bromodifluoroacetate With copper In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-bromo-5-cyanopyridine In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere;	86%

(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl)(difluoromethyl)silver + 2-bromo-5-cyanopyridine (139585-70-9) → C7H4F2N2

Conditions	Yield
With bis[2-(diphenylphosphino)phenyl] ether; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; Inert atmosphere;	88%

(C5Me5)2Ti(η(2)-bis(trimethylsilyl)acetylene) (128541-33-3) + 2-bromo-5-cyanopyridine (139585-70-9) → C32H36Br2N4Ti

Conditions	Yield
In hexane; toluene for 24h;	87%

tert-butyl 6-cyano-2-(trimethylstannyl)-1H-indole-1-carboxylate + 2-bromo-5-cyanopyridine (139585-70-9) → 1-(tert-butoxycarbonyl)-2-(5-cyanopyridin-2-yl)-1H-indole-6-carbonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90 - 100℃; for 24h; Stille Cross Coupling; Inert atmosphere;	87%

methyl 4-iodobenzoate (619-44-3) + 2-bromo-5-cyanopyridine (139585-70-9) → methyl 4-(5-cyano-2-pyridyl)benzoate

Conditions	Yield
Stage #1: methyl 4-iodobenzoate With isopropylmagnesium chloride In tetrahydrofuran; diethyl ether at -40℃; for 0.666667h; Stage #2: 2-bromo-5-cyanopyridine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at -40℃; for 6h;	86%
Stage #1: methyl 4-iodobenzoate With isopropylmagnesium chloride In tetrahydrofuran at -40℃; for 0.666667h; Stage #2: 2-bromo-5-cyanopyridine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at -40℃; for 6h;	86%

4-propoxybenzimidazole (1351990-78-7) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-(4-propoxy-1H-benzo[d]imidazol-1-yl)nicotinonitrile

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	86%

ethylamine (75-04-7) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-(ethylamino)nicotinonitrile (1016813-34-5)

Conditions	Yield
In tetrahydrofuran at 80 - 100℃; for 6h; Sealed tube;	86%

4-methylphenylboronic acid (5720-05-8) + 2-bromo-5-cyanopyridine (139585-70-9) → 6-(4-methylphenyl)nicotinonitrile

Conditions	Yield
Stage #1: 2-bromo-5-cyanopyridine With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 0.25h; Suzuki Coupling; Inert atmosphere; Stage #2: 4-methylphenylboronic acid In ethanol; water; toluene at 80℃; for 48h; Suzuki Coupling; Inert atmosphere;	85%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2-bromo-5-cyanopyridine (139585-70-9) → Methyl 5-cyanopyridine-2-carboxylate (76196-66-2)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In N,N-dimethyl-formamide at 60℃; under 2585.81 Torr; for 14h;	85%

Upstream product

• 122306-01-8 2-bromo-5-(hydroxymethyl)pyridine 
• 864266-28-4 C₆H₅BrN₂O 
• 149806-06-4 6-bromonicotinaldehyde 
• 557-21-1 zinc(II) cyanide 
• 223463-14-7 6-bromopyridin-3-ylboronic acid 
• 33252-28-7 6-chloronicotinonitrile 

Downstream Products

• 39065-54-8 2-phenyl-5-cyanopyridine 
• 149353-77-5 6-(4-methoxyphenyl)nicotinonitrile 
• 928649-63-2 6-(3,3-dimethyl-2-oxo-butoxy)-pyridine-3-carbonitrile 
• 43083-19-8 2-phenyl-5-amidopyridine 
• 889676-37-3 6-bromopyridine-3-carboxamide 

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