197958-29-5

Basic information

• Product Name: 2-Pyridineboronic acid
• Synonyms: PYRIDIN-2-YLBORONIC ACID;PYRIDIN-2-YL-2-BORONIC ACID;PYRIDINE-2-BORONIC ACID;2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE;2-PYRIDINEBORNIC ACID;2-PYRIDINEBORONIC ACID;2-PYRIDINYLBORONIC ACID;Boronic acid, 2-pyridinyl- (9CI)
• CAS NO: 197958-29-5
• Molecular Formula: C₅H₆BNO₂
• Molecular Weight: 122.92
• Product Categories: PYRIDINE;blocks;BoronicAcids;Pyridines;Boronic Acids & Esters;Boronic acid;Boronic Acids & Esters
• Mol File: 197958-29-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: >300
• Boiling Point: 308.782 °C at 760 mmHg
• Flash Point: 140.547 °C
• Appearance: White to light yellow crystal powder
• Density: 1.23 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Store below -20C
• PKA: 7.79±0.53(Predicted)
• CAS DataBase Reference: 2-Pyridineboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridineboronic acid(197958-29-5)
• EPA Substance Registry System: 2-Pyridineboronic acid(197958-29-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36/37/39-39
• WGK Germany: 3
• Hazardous Substances Data: 197958-29-5(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powder

Uses

2-Pyridineboronic Acid is used in organic synthesis as a reagent in Suzuki cross-coupling reactions, for example in the synthesis of aryl- and heteroaryl-substituted 3-benzyloxyisothiazoles and novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines.

InChI:InChI=1/C5H6BNO2/c8-6(9)5-3-1-2-4-7-5/h1-4,8-9H

Synthetic route

2-bromo-pyridine (109-04-6) + Triisopropyl borate (5419-55-6) → pyridin-2-ylboronic acid (197958-29-5)

Conditions	Yield
Stage #1: 2-bromo-pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; hexane; toluene at -30℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene at 20℃; for 1h; Inert atmosphere;	81%
Stage #1: 2-bromo-pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; toluene at 20℃; for 1h;	81%
With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere;	81%
Stage #1: 2-bromo-pyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃;	73%

2-bromo-pyridine (109-04-6) + Trimethyl borate (121-43-7) → pyridin-2-ylboronic acid (197958-29-5)

Conditions	Yield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h;	77%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	66.8%

2-bromo-pyridine (109-04-6) → pyridin-2-ylboronic acid (197958-29-5)

Conditions	Yield
Stage #1: 2-bromo-pyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Stage #2: With tris(trimethylsilyl)borate In tetrahydrofuran at 0 - 20℃; for 24h; Stage #3: With hydrogenchloride at 0℃; pH=6 - 7;	70%

C31H28N2O2 + pyridin-2-ylboronic acid (197958-29-5) → C36H30BN3O2

Conditions	Yield
In methanol; toluene for 15h; Inert atmosphere; Reflux;	99%

pyridin-2-ylboronic acid (197958-29-5) → 2-hydroxypyridin (142-08-5)

Conditions	Yield
With hydrazine hydrate; caesium carbonate In water at 80℃; for 12h;	96%

potassium cyanide + pyridin-2-ylboronic acid (197958-29-5) → 5-(2-pyridyl)-1H-tetrazole (33893-89-9)

Conditions	Yield
With sodium azide; potassium carbonate In ethanol; water for 5h; Catalytic behavior; Reflux; Inert atmosphere; Green chemistry;	96%

C29H20BBrN2 + pyridin-2-ylboronic acid (197958-29-5) → C34H24BN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 110℃; for 3h; Inert atmosphere;	95%

pyridin-2-ylboronic acid (197958-29-5) + thiophenol (108-98-5) → 2-phenylsulfanylpyridine (3111-54-4)

Conditions	Yield
With copper slag In N,N-dimethyl-formamide at 100℃; for 0.166667h; Temperature; Wavelength; Microwave irradiation; Green chemistry;	94%

3,7-dibromo-1,8-naphthyridine (72754-04-2) + pyridin-2-ylboronic acid (197958-29-5) → C13H8BrN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 8h; Inert atmosphere; Reflux;	93.7%

2-bromo-5-iodophenol (932372-99-1) + pyridin-2-ylboronic acid (197958-29-5) → C11H8BrNO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 5h; Inert atmosphere;	93%

C31H18BrCl + pyridin-2-ylboronic acid (197958-29-5) → C36H22ClN

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In toluene at 100℃; for 12h;	92.5%

6-bromo-N,N-diphenylanthracen-2-amine + pyridin-2-ylboronic acid (197958-29-5) → C30H21N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 80℃; Inert atmosphere;	92%

2,3-bis(bromomethyl)quinoxaline (3138-86-1) + broxyquinoline (521-74-4) + pyridin-2-ylboronic acid (197958-29-5) → 4,6-di(pyridin-2-yl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]oxazocino[6,7-b]-quinoxalin-1-one

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	92%

benzoimidazole (51-17-2) + pyridin-2-ylboronic acid (197958-29-5) → 1-pyridin-2-yl-1H-benzoimidazole (25660-37-1)

Conditions	Yield
With 2Na(1+)*CuC6H4(NCHC6H3OO3S)2(2-)=CuC6H4(NCHC6H3ONaO3S)2 In water at 100℃; for 6h;	90%

7-(2-chlorophenyl)-2-(3-methylbenzofuran-2-yl)-5,6,7,8-tetrahydro-4H-benzo[4,5]imidazo[1,2-b]pyrazole-3-carbonitrile + pyridin-2-ylboronic acid (197958-29-5) → 2-(3-methylbenzofuran-2-yl)-7-(2-(pyridin-2-yl)phenyl)-5,6,7,8-tetrahydro-4H-benzo[4 ,5]imidazo[1,2-b]pyrazole-3-carbonitrile

Conditions	Yield
With potassium carbonate In ethanol; water at 60℃; for 0.5h; Inert atmosphere;	90%

5-bromo-4-cyclopentyl-1H-pyrrole-2-carboxylic acid (4-methylcyclohexyl)ester + pyridin-2-ylboronic acid (197958-29-5) → 4-methylcyclohexyl 4-cyclopentyl-5-(pyridin-2-yl)-1H-pyrrole-2-carboxylate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Microwave irradiation; Inert atmosphere;	90%

7-(5-bromo-2-fluorophenyl)-1-methyloctahydro-1H-pyrrolo[2,3-b]pyridine + pyridin-2-ylboronic acid (197958-29-5) → 7-(2-fluoro-5-(pyridin-2-yl)phenyl)-1-methyloctahydro-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 60℃; for 0.166667h; Inert atmosphere;	89%

pyridin-2-ylboronic acid (197958-29-5) + chlorobenzene (108-90-7) → 2-phenylpyridine (1008-89-5)

Conditions	Yield
Stage #1: pyridin-2-ylboronic acid; chlorobenzene With potassium phosphate In para-xylene at 128℃; for 1.5h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; Microwave irradiation; Stage #2: In ethanol; para-xylene; water at 130℃; for 24h; Sealed tube; Inert atmosphere;	89%

4-((4-bromo-5-(4-methoxyphenyl)-2H-1,2,3-triazol-2-yl)methyl)benzonitrile (1384848-86-5) + pyridin-2-ylboronic acid (197958-29-5) → 4-[4-(4-methoxy-phenyl)-5-pyridin-2-yl-[1,2,3]triazol-2-ylmethyl]-benzonitrile (710947-00-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate In water; acetonitrile at 85℃; Suzuki-Miyaura coupling; chemoselective reaction;	88%

pyridin-2-ylboronic acid (197958-29-5) + para-Chlorobenzyl alcohol (873-76-7) → (4-(pyridine-2-yl)phenyl)methanol (98061-39-3)

Conditions	Yield
With C38H37ClN4O2Pd; potassium carbonate In butan-1-ol at 100℃; for 36h; Inert atmosphere; Schlenk technique;	88%

carbon monoxide (201230-82-2) + toluene-4-sulfonic acid phenyl ester (640-60-8) + pyridin-2-ylboronic acid (197958-29-5) → phenyl(pyridin-2-yl)methanone (91-02-1)

Conditions	Yield
With palladium(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl acetamide at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling;	87%

C8H8BrNOS + pyridin-2-ylboronic acid (197958-29-5) → C13H12N2OS

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; Suzuki Coupling; Inert atmosphere;	87%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 80℃; Inert atmosphere;	87%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; Suzuki Coupling; Inert atmosphere;	87%

pyridin-2-ylboronic acid (197958-29-5) → [2,2]bipyridinyl (366-18-7)

Conditions	Yield
With palladium diacetate at 20℃; for 0.5h;	87%
With potassium phosphate In 1,4-dioxane at 85℃; for 3h; Catalytic behavior; Suzuki Coupling; Green chemistry;	82%
With nano-CuO-grafted triazine-functionalized covalent organic framework In methanol at 60℃; Catalytic behavior;	59%

C12H13ClN2O2Si + pyridin-2-ylboronic acid (197958-29-5) → C17H17N3O2Si

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;	87%

3-Bromonitrobenzene (585-79-5) + pyridin-2-ylboronic acid (197958-29-5) → 2-(3-nitrophenyl)pyridine (4253-79-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 80 - 100℃; Inert atmosphere;	86%

4-chloropyrimidine (17180-93-7) + pyridin-2-ylboronic acid (197958-29-5) → 2-(pyrimidin-4-yl)pyridine (52997-82-7)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In water at 60℃; for 8h; Suzuki coupling;	85%

carbon monoxide (201230-82-2) + Phenyl triflate (17763-67-6) + pyridin-2-ylboronic acid (197958-29-5) → phenyl(pyridin-2-yl)methanone (91-02-1)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium(II) trifluoroacetate In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling;	85%

ethyl 5-bromo-4-cyclopentyl-1H-pyrrole-2-carboxylate + pyridin-2-ylboronic acid (197958-29-5) → ethyl 4-cyclopentyl-5-(pyridin-2-yl)-1H-pyrrole-2-carboxylate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Microwave irradiation; Inert atmosphere;	85%

1H-imidazole (288-32-4) + pyridin-2-ylboronic acid (197958-29-5) → 2-(1H-imidazolyl)pyridine (25700-14-5)

Conditions	Yield
With 2Na(1+)*CuC6H4(NCHC6H3OO3S)2(2-)=CuC6H4(NCHC6H3ONaO3S)2 In water at 100℃; for 6h;	83%

(S)-3-(4-(5-bromo-2-fluoropyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1456506-83-4) + pyridin-2-ylboronic acid (197958-29-5) → (S)-3-(4-(6-fluoro-[3,3'-bipyridin]-5-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1456505-78-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube; Microwave irradiation;	83%

pyridin-2-ylboronic acid (197958-29-5) → 2-aminopyridine (504-29-0)

Conditions	Yield
With N-Bromosuccinimide; N-methoxylamine hydrochloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃;	83%
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 1h; chemoselective reaction;	77%

C16H9BrClN3 + pyridin-2-ylboronic acid (197958-29-5) → C21H13ClN4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Reflux;	83%

2,9-dichloro-4,7-diphenyl-1,10-phenanthroline (1229012-68-3) + pyridin-2-ylboronic acid (197958-29-5) → C34H22N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Inert atmosphere; Reflux;	83%

Upstream product

• 109-04-6 2-bromo-pyridine 
• 121-43-7 Trimethyl borate 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 1310064-17-5 C₂₈H₂₇N₅O 
• 4467-06-5 2-(4-methylphenyl)pyridine 
• 1072854-66-0 (3S)-N,N-dibenzyl-5-pyridin-2-ylchroman-3-amine 
• 1313412-13-3 10-(3-bromo-5-(pyridin-2-yl)phenyl)-10H-phenothiazine 
• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 142-08-5 2-hydroxypyridin 
• 33893-89-9 5-(2-pyridyl)-1H-tetrazole 
• 924628-39-7 3-(4-pyridin-2-ylphenyl)propanoic acid 

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