5-Fluoropyridin-3-ylboronic acid supplier

Name
5-Fluoropyridin-3-ylboronic acid
EINECS 640-175-6
CAS No. 872041-86-6
Density 1.34 g/cm³
Solubility
Melting Point 233-236 °C
Formula C₅H₅BFNO₂
Boiling Point 292.9 °C at 760 mmHg
Molecular Weight 140.91
Flash Point 130.9 °C
Transport Information
Appearance off-white solid
Safety 26-39-37
Risk Codes 37/38-41-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Boronicacid, (5-fluoro-3-pyridinyl)- (9CI);(3-Fluoropyridin-5-yl)boronic acid;(5-Fluoropyridin-3-yl)boronic acid;
PSA 53.35000
LogP -1.09950

Synthetic route

: 407-20-5
3-bromo-5-fluoropyridine

: 872041-86-6
5-fluoropyridine-3-boronic acid

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1338094-46-4
7-bromo-3,3-dimethyl-3,4-dihydro-2H,5′Hspiro[naphthalene-1,4′-oxazol]-2′-amine

: 1338092-82-2
7-(2-fluoropyridin-3-yl)-3,3-dimethyl-3,4-dihydro-2H,5′(1'H)-spiro[naphthalene-1,4′-oxazol]-2′-amine

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 5,5'-difluoro-3,3'-bipyridine

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 6-bromo-5-methyl-3,4-dihydroisoquinolin-1(2H)-one

: 6-(5-fluoropyridin-3-yl)-5-methyl-3,4-dihydroisoquinolin-1(2H)-one

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1428066-17-4
5-bromo-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide

: 1428066-19-6
5-(5-fluoropyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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

: 869120-25-2
1-chloro-7-methoxynaphthalen-2-yl trifluoromethanesulfonate

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1447449-89-9
3-(1-chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: (±)-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

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 5-bromo-3-(prop-1-en-2-yl)pyrazin-2-amine

: 5-(5-fluoro-3-pyridyl)-3-isopropenyl-pyrazin-2-amine

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: tert-butyl N-[6-chloro-2-(trifluoromethyl)-3-pyridyl]carbamate

: tert-butyl N-[6-(5-fluoro-3-pyridyl)-2-(trifluoromethyl)-3-pyridyl]carbamate

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: (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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 4522-35-4
3-iodo-1H-pyrazole

: C8H5FIN3

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 3,6-dichloro-2-(trifluoromethyl)pyridine

: 3-chloro-6-(5-fluoro-3-pyridyl)-2-(trifluoromethyl)pyridine

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1616416-09-1
2-bis-(tert-butoxycarbonyl)amino-3-methyl-5-bromopyrazine

: 2-bis(tert-butoxycarbonyl)amino-3-methyl-5-(5-fluoropyrid-3-yl)pyrazine

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 115375-60-5
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

: 3β-acetoxy-17-(5-fluoropyridin-3-yl)androsta-5,16-diene

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1427000-64-3
4,5,6,7-tetrahydro-3-(2,6-dibromophenyl)-(3H)-benzothiazole-2-thione

: 4,5,6,7-tetrahydro-3-[2,6-bis(5-fluoro-3-pyridyl)phenyl]-2(3H)-benzothiazolethione

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: (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

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 95667-45-1
(8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate

: 17-(5-fluoropyridin-3-yl)-3-methoxyestra-1,3,5(10),16-tetraene

Conditions

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%

: 1809-20-7
diisopropyl hydrogenphosphonate

: 872041-86-6
5-fluoropyridine-3-boronic acid

: diisopropyl (5-fluoro-3-pyridinyl)phosphonate

Conditions

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

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1338484-01-7
(S)-benzyl 1-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)ethylcarbamate

: 1338484-00-6
(S)-benzyl 1-(6-fluoro-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)ethylcarbamate

Conditions

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;

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 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

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: 1147077-78-8
C28H28BrN3O5

: 2-amino-8-((5-fluoropyridin-3-yl)methyl)-4-phenyl-5H-indeno-[1,2-d]pyrimidin-5-one di-hydrochloride

Conditions

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%

: 872041-86-6
5-fluoropyridine-3-boronic acid

: di(tert-butyl) 2-bromo-1,3-thiazol-5-ylimidodicarbonate

: di(tert-butyl) 2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate

Conditions

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

5-Fluoropyridin-3-ylboronic acid Specification

The 5-Fluoropyridin-3-ylboronic acid, with its CAS registry number 872041-86-6, has the systematic name of (5-fluoro-3-pyridyl)boronic acid. And its product categories are including blocks; BoronicAcids; Pyridines. Besides, it is irritant which may cause inflammation to the skin or other mucous membranes, so you should be careful while using.

The characteristics of 5-Fluoropyridin-3-ylboronic acid are as below: (1)ACD/LogP: 0.14; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 3; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 53.35; (7)Index of Refraction: 1.507; (8)Molar Refractivity: 31.19 cm³; (9)Molar Volume: 104.8 cm³; (10)Polarizability: 12.36×10^-24 cm³; (11)Surface Tension: 47 dyne/cm; (12)Density: 1.34 g/cm³; (13)Flash Point: 130.9 °C; (14)Enthalpy of Vaporization: 56.23 kJ/mol; (15)Boiling Point: 292.9 °C at 760 mmHg; (16)Vapour Pressure: 0.000813 mmHg at 25°C.

In addition, you could convert the following datas into the molecular structure:
(1)SMILES:B(c1cc(cnc1)F)(O)O
(2)InChI:InChI=1/C5H5BFNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H
(3)InChIKey:FVEDGBRHTGXPOK-UHFFFAOYAW

Product Name

5-Fluoropyridin-3-ylboronic acid

Synthetic route

5-Fluoropyridin-3-ylboronic acid Specification

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