872041-86-6

Basic information

• Product Name: 5-Fluoropyridin-3-ylboronic acid
• Synonyms: 5-fluoro-3-pyridylboronic acid;5-Fluoropyridine-3-boronic acid 98%;5-Fluoropyridine-3-boronicacid98%;5-fluoropyridin-3-yl-3-boronic acid;3-Fluoropyridin-5-ylboronic acid;3-Borono-5-fluoropyridine;B-(5-fluoro-3-pyridinyl)-Boronic acid;5-Fluoropyridine-3-boronic Acid (contains varying aMounts of Anhydride)
• CAS NO: 872041-86-6
• Molecular Formula: C₅H₅BFNO₂
• Molecular Weight: 140.91
• EINECS: 1533716-785-6
• Product Categories: blocks;BoronicAcids;Pyridines
• Mol File: 872041-86-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 233-236
• Boiling Point: 292.9 °C at 760 mmHg
• Flash Point: 130.9 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.34 g/cm³
• Vapor Pressure: 0.000813mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Keep Cold
• Solubility: Soluble in hot methanol.
• PKA: 5.85±0.10(Predicted)
• CAS DataBase Reference: 5-Fluoropyridin-3-ylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoropyridin-3-ylboronic acid(872041-86-6)
• EPA Substance Registry System: 5-Fluoropyridin-3-ylboronic acid(872041-86-6)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-37
• Hazardous Substances Data: 872041-86-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 872041-86-6 differently. You can refer to the following data:
1. suzuki reaction
2. 5-Fluoropyridine-3-boronic acid is used as pharmaceutical intermediate.

InChI:InChI=1/C5H5BFNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H

Synthetic route

3-bromo-5-fluoropyridine (407-20-5) → 5-fluoropyridine-3-boronic acid (872041-86-6)

Conditions	Yield
Stage #1: 3-bromo-5-fluoropyridine With n-butyllithium; Triisopropyl borate In tetrahydrofuran at -90 - -80℃; for 2.5h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at -20 - 10℃; pH=1 - 2; Stage #3: With sodium hydroxide In water pH=6;	87.4%

5-fluoropyridine-3-boronic acid (872041-86-6) + 7-bromo-3,3-dimethyl-3,4-dihydro-2H,5′Hspiro[naphthalene-1,4′-oxazol]-2′-amine (1338094-46-4) → 7-(2-fluoropyridin-3-yl)-3,3-dimethyl-3,4-dihydro-2H,5′(1'H)-spiro[naphthalene-1,4′-oxazol]-2′-amine (1338092-82-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 85℃; for 12h; Suzuki Coupling; Sealed tube; Inert atmosphere;	95%

5-fluoropyridine-3-boronic acid (872041-86-6) → 5,5'-difluoro-3,3'-bipyridine

Conditions	Yield
With copper(II) choride dihydrate; sodium carbonate In methanol at 25℃; for 0.25h; Green chemistry;	93%

5-fluoropyridine-3-boronic acid (872041-86-6) + tert butyl N-[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbamate → tert-butyl N-[2-(5-fluoro-3-pyridyl)-4-(trifluoromethyl)pyrimidin-5-yl]carbamate

Conditions	Yield
Stage #1: 5-fluoropyridine-3-boronic acid; tert butyl N-[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbamate In ethanol; water; toluene at 20℃; for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 8h; Inert atmosphere;	93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 8h; Inert atmosphere;	93%

5-fluoropyridine-3-boronic acid (872041-86-6) + tert-butyl 7-chloro-3,4-dihydro-1,4-ethanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxylate → tert-butyl 7-(5-fluoropyridin-3-yl)-3,4-dihydro-1,4-ethanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxylate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 110℃; for 12h;	89%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 110℃; for 12h;	89%

5-fluoropyridine-3-boronic acid (872041-86-6) + 6-bromo-5-methyl-3,4-dihydroisoquinolin-1(2H)-one → 6-(5-fluoropyridin-3-yl)-5-methyl-3,4-dihydroisoquinolin-1(2H)-one

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	89%

5-fluoropyridine-3-boronic acid (872041-86-6) + 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide (1428066-17-4) → 5-(5-fluoropyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide (1428066-19-6)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 90℃; for 3h; Suzuki Coupling; Inert atmosphere;	88%
In water; N,N-dimethyl-formamide at 90℃;	88%

5-fluoropyridine-3-boronic acid (872041-86-6) + 6-bromo-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide → 5'-fluoro-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3'-bipyridine]-6-carboxamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 150℃; for 1h; Microwave irradiation;	88%

1-chloro-7-methoxynaphthalen-2-yl trifluoromethanesulfonate (869120-25-2) + 5-fluoropyridine-3-boronic acid (872041-86-6) → 3-(1-chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine (1447449-89-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 8h; Suzuki Coupling; Inert atmosphere; Reflux;	87%

5-fluoropyridine-3-boronic acid (872041-86-6) + (±)-methyl 1-(3-fluoro-2-methyl-phenyl)-3-(trifluoromethylsulfonyloxy)cyclopent-2-ene-1-carboxylate → (±)-methyl 1-(3-fluoro-2-methyl-phenyl)-3-(5-fluoropyridin-3-yl)cyclopent-2-ene-1-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In methanol; 1,2-dimethoxyethane at 120℃; for 1h; Microwave irradiation;	87%

5-fluoropyridine-3-boronic acid (872041-86-6) + ethyl 3-oxo-6-[6-(trifluoromethyl)pyridin-3-yl]-2,3-dihydropyridazine-4-carboxylate → ethyl 2-(5-fluoropyridin-3-yl)-3-oxo-6-[6-(trifluoromethyl)pyridin-3-yl]-2,3-dihydropyridazine-4-carboxylate

Conditions	Yield
With pyridine; copper diacetate; triethylamine In acetonitrile at 80℃; for 3h;	86%

5-fluoropyridine-3-boronic acid (872041-86-6) + 5-bromo-3-(prop-1-en-2-yl)pyrazin-2-amine → 5-(5-fluoro-3-pyridyl)-3-isopropenyl-pyrazin-2-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water for 3h; Reflux;	86%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water for 3h; Reflux;	86%

5-fluoropyridine-3-boronic acid (872041-86-6) + tert-butyl 4-(4-(6-chloropyrazin-2-yl)benzoyl)piperazine-1-carboxylate → tert-butyl 4-(4-(6-(5-fluoropyridin-3-yl)pyrazin-2-yl)benzoyl)piperazine-1-carboxylate

Conditions	Yield
Stage #1: 5-fluoropyridine-3-boronic acid; tert-butyl 4-(4-(6-chloropyrazin-2-yl)benzoyl)piperazine-1-carboxylate With potassium carbonate In 1,2-dimethoxyethane; water for 0.0833333h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 65℃; for 4.5h;	85%

5-fluoropyridine-3-boronic acid (872041-86-6) + tert-butyl N-[6-chloro-2-(trifluoromethyl)-3-pyridyl]carbamate → tert-butyl N-[6-(5-fluoro-3-pyridyl)-2-(trifluoromethyl)-3-pyridyl]carbamate

Conditions	Yield
With 9-{[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenyl-λ4-phosphanyl}-O-methanesulfonyl-8-methyl-8λ4-aza-9-palladatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene-9,9-bis(ylium)-10-uid-9-olate; potassium carbonate In ethanol; water; toluene for 3h; Reflux;	85%
With xantphos PDG4; potassium carbonate In ethanol; water; toluene for 3h; Reflux;	85%
With methanesulfonato[9,9-dimethyl-4,5-bis-(diphenylphosphino)xanthene](2'-methylamino-1,1'-biphenyl-2-yl)-palladium(II); potassium carbonate In ethanol; toluene for 3h; Reflux;	85%

5-fluoropyridine-3-boronic acid (872041-86-6) + (R)-6-bromo-2-(3-(1,1,2-trifluoro-1-(4-methyl-4H-1,2,4-triazol-3-yl)propan-2-yl)phenyl)-4-(trifluoromethyl)isoindolin-1-one → (R)-6-(5-fluoropyridin-3-yl)-2-(3-(1,1,2-trifluoro-1-(4-methyl-4H-1,2,4-triazol-3-yl)propan-2-yl)phenyl)-4-(trifluoromethyl)isoindolin-1-one

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 0.25h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	85%

5-fluoropyridine-3-boronic acid (872041-86-6) + 3-iodo-1H-pyrazole (4522-35-4) → C8H5FIN3

Conditions	Yield
With pyridine; pyridine N-oxide; oxygen; copper diacetate In dichloromethane at 20℃; for 48h;	84.82%

5-fluoropyridine-3-boronic acid (872041-86-6) + 3,6-dichloro-2-(trifluoromethyl)pyridine → 3-chloro-6-(5-fluoro-3-pyridyl)-2-(trifluoromethyl)pyridine

Conditions	Yield
With xantphos PDG4; potassium carbonate In ethanol; water; toluene at 80℃; for 2.5h; Inert atmosphere;	84%
With methanesulfonato[9,9-dimethyl-4,5-bis-(diphenylphosphino)xanthene](2'-methylamino-1,1'-biphenyl-2-yl)-palladium(II); potassium carbonate In water; toluene at 80℃; for 2.5h; Inert atmosphere;	84%
With 9-{[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenyl-λ4-phosphanyl}-O-methanesulfonyl-8-methyl-8λ4-aza-9-palladatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene-9,9-bis(ylium)-10-uid-9-olate; potassium carbonate In ethanol; water; toluene at 80℃; for 2.5h; Inert atmosphere;	75%

5-fluoropyridine-3-boronic acid (872041-86-6) + 2-bis-(tert-butoxycarbonyl)amino-3-methyl-5-bromopyrazine (1616416-09-1) → 2-bis(tert-butoxycarbonyl)amino-3-methyl-5-(5-fluoropyrid-3-yl)pyrazine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water for 0.25h; Reflux;	84%

5-fluoropyridine-3-boronic acid (872041-86-6) + N-[5-(7-bromo-8-fluoro-4-oxoquinazolin-3 (4H)-yl)-2-(trifluoromethoxy)phenyl]-2-(morpholin-4-yl)propanamide → N-{5-[8-fluoro-7-(5-fluoropyridin-3-yl)-4-oxoquinazolin-3(4H)-yl]-2-(trifluoromethoxy)phenyl}-2-(morpholin-4-yl)propanamide

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	84%

5-fluoropyridine-3-boronic acid (872041-86-6) + methyl 3'-fluoro-2'-methyl-4-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-1-carboxylate → methyl 3'-fluoro-4-(5-fluoropyridin-3-yl)-2'-methyl-1,2,3,6-tetrahydro-[1,1'-biphenyl]-1-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In methanol; 1,2-dimethoxyethane at 120℃; for 2h; Sealed tube; Microwave irradiation;	83%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In methanol; 1,2-dimethoxyethane at 120℃; for 2h; Sealed tube; Microwave irradiation;	83%

5-fluoropyridine-3-boronic acid (872041-86-6) + tert-butyl N-methyl-N-{[17-{[(trifluoromethyl)sulfonyl]oxy}estra-1(10),2,4,16-tetraen-3-yl]sulfonyl}-beta-alaninate → tert-butyl N-{[17-(5-fluoropyridin-3-yl)estra-1(10),2,4,16-tetraen-3-yl]sulfonyl}-N-methyl-beta-alaninate

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; for 2h; Sealed tube;	83%

5-fluoropyridine-3-boronic acid (872041-86-6) + 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate (115375-60-5) → 3β-acetoxy-17-(5-fluoropyridin-3-yl)androsta-5,16-diene

Conditions	Yield
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry; Stage #2: 5-fluoropyridine-3-boronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry;	83%

5-fluoropyridine-3-boronic acid (872041-86-6) + 4,5,6,7-tetrahydro-3-(2,6-dibromophenyl)-(3H)-benzothiazole-2-thione (1427000-64-3) → 4,5,6,7-tetrahydro-3-[2,6-bis(5-fluoro-3-pyridyl)phenyl]-2(3H)-benzothiazolethione

Conditions	Yield
With palladium diacetate; cesium fluoride; johnphos In tetrahydrofuran at 60℃; for 8h; Inert atmosphere;	83%

5-fluoropyridine-3-boronic acid (872041-86-6) + (S)-methyl 1-(3-fluoro-2-methylphenyl)-3-(((trifluoromethyl)sulfonyl)oxy)cyclopent-2-enecarboxylate → (S)-methyl 1-(3-fluoro-2-methylphenyl)-3-(5-fluoropyridin-3-yl)cyclopent-2-enecarboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 100℃; for 2h; Suzuki Coupling; Inert atmosphere;	81%

5-fluoropyridine-3-boronic acid (872041-86-6) + (8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate (95667-45-1) → 17-(5-fluoropyridin-3-yl)-3-methoxyestra-1,3,5(10),16-tetraene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; lithium chloride In ethanol; water; toluene for 4.5h; Reflux;	81%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; lithium chloride In ethanol; toluene for 4.5h; Reflux;	81%

diisopropyl hydrogenphosphonate (1809-20-7) + 5-fluoropyridine-3-boronic acid (872041-86-6) → diisopropyl (5-fluoro-3-pyridinyl)phosphonate

Conditions	Yield
With triphenylphosphine; palladium dichloride; silver(l) oxide at 100℃; for 2h; Inert atmosphere;	80%

5-fluoropyridine-3-boronic acid (872041-86-6) + (S)-benzyl 1-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)ethylcarbamate (1338484-01-7) → (S)-benzyl 1-(6-fluoro-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)ethylcarbamate (1338484-00-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 100℃; for 2h; Suzuki Coupling;	76%
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 110℃; for 2h; Microwave irradiation;

5-fluoropyridine-3-boronic acid (872041-86-6) + 2-chloro-N-[2-(1H-indol-3-yl)ethyl]-7-isopropenylthieno[3,2-d]pyrimidin-4-amine → N-(2-(1H-indol-3-yl)ethyl)-2-(5-fluoropyridin-3-yl)-7-(prop-1-en-2-yl)thieno[3,2-d]pyrimidin-4-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation; Sealed tube; Inert atmosphere;	74.49%

5-fluoropyridine-3-boronic acid (872041-86-6) + C28H28BrN3O5 (1147077-78-8) → 2-amino-8-((5-fluoropyridin-3-yl)methyl)-4-phenyl-5H-indeno-[1,2-d]pyrimidin-5-one di-hydrochloride

Conditions	Yield
Stage #1: 5-fluoropyridine-3-boronic acid; C28H28BrN3O5 With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; Suzuki coupling; Microwave irradiation; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether	74%

5-fluoropyridine-3-boronic acid (872041-86-6) + di(tert-butyl) 2-bromo-1,3-thiazol-5-ylimidodicarbonate → di(tert-butyl) 2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 0.75h; Reflux;	73%

Upstream product

• 407-20-5 3-bromo-5-fluoropyridine 

Downstream Products

• 1259380-35-2 (4-(5-fluoropyridin-3-yl)phenyl)(7'-methoxy-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline]-1-yl)methanone hydrochloride 
• 1428432-79-4 2-(5-fluoropyridin-3-yl)-3-phenylpyrazolo[1,5-a]pyridine 
• 1455094-16-2 1-(5-fluoropyridin-3-yl)-4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid methyl ester 
• 1392839-52-9 1-benzyl-5-(5-fluoro-pyridin-3-yl)-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester 
• 1392839-26-7 7-benzyl-1-(5-fluoro-pyridin-3-yl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester 
• 1383847-04-8 5-(3-Amino-4-fluoro-1-(3-(5-fluoropyridin-3-yl)phenyl)-1H-isoindol-1-yl)-3-(difluoromethyl)-1-ethylpyridin-2(1H)-one 
• 1382993-90-9 N-{1-[5-Chloro-3-(5-fluoropyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}-9H-purin-6-amine 
• 1338484-00-6 (S)-benzyl 1-(6-fluoro-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)ethylcarbamate 
• 1260432-28-7 2-(3-(5-fluoropyridin-3-yl)phenyl)-2-(4-methoxy-3-methylphenyl)-5-methyl-2H-imidazol-4-amine 
• 1231304-56-5 2-(((1s,4s)-4-((4-(5-fluoropyridin-3-yl)-5-(methylthio)-3-phenyl-1H-pyrazol-1-yl)methyl)cyclohexyl)methoxy)acetic acid 
• 1216935-53-3 C₁₉H₂₁F₂N₇ 
• 1097633-60-7 1-[3-(5-fluoropyridin-3-yl)phenyl]-1-[4-(methylsulfonyl)phenyl]-1H-isoindol-3-amine 

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