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1692-25-7

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1692-25-7 Usage

Description

3-Pyridylboronic acid is an organic compound that serves as a versatile reagent in various chemical reactions. It is a light yellow powder and is commonly used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-Pyridylboronic acid is used as a reagent for the synthesis of various pharmaceuticals and agrochemicals. It plays a crucial role in the development of new drugs and pesticides, contributing to the advancement of these industries.
Used in Suzuki Reaction:
3-Pyridylboronic acid is used as a reagent in the Suzuki reaction, a type of phosphine-free Suzuki-Miyaura cross-coupling reaction. This reaction is essential for the formation of new linear poly(phenylpyridyl) chains and the synthesis of oligopyridyl foldamers, which serve as mimics of alpha-helix twist.
Used in Regioselective Suzuki-Miyaura Coupling and Tandem Palladium-Catalyzed Intramolecular Aminocarbonylation and Annulation:
3-Pyridylboronic acid is used as a reagent for regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation. This process allows for the selective formation of specific compounds, which is crucial in the synthesis of complex organic molecules.
Used in N-Arylation Using Copper Acetylacetonate Catalyst:
3-Pyridylboronic acid is used as a reagent in N-arylation reactions using a copper acetylacetonate catalyst. This process is vital for the synthesis of various organic compounds, including those with potential therapeutic applications.
Used in Copper-Mediated Cyanation and Regioselective Cyanation of Electron-Rich Benzenes:
3-Pyridylboronic acid is used as a reagent in copper-mediated cyanation and regioselective cyanation of electron-rich benzenes. This reaction is essential for the synthesis of various organic compounds, including those with potential applications in the pharmaceutical and agrochemical industries.
Used in Preparation of Highly Significant Therapeutic Enzymatic and Kinase Inhibitors:
3-Pyridylboronic acid is used as a reagent in the preparation of highly significant therapeutic enzymatic and kinase inhibitors. These inhibitors play a crucial role in the development of new drugs for the treatment of various diseases and conditions.

Synthesis Reference(s)

The Journal of Organic Chemistry, 64, p. 3846, 1999 DOI: 10.1021/jo9819279Tetrahedron Letters, 43, p. 4285, 2002

Check Digit Verification of cas no

The CAS Registry Mumber 1692-25-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,9 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1692-25:
(6*1)+(5*6)+(4*9)+(3*2)+(2*2)+(1*5)=87
87 % 10 = 7
So 1692-25-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H

1692-25-7 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (L15040)  Pyridine-3-boronic acid   

  • 1692-25-7

  • 1g

  • 755.0CNY

  • Detail
  • Alfa Aesar

  • (L15040)  Pyridine-3-boronic acid   

  • 1692-25-7

  • 5g

  • 2608.0CNY

  • Detail
  • Aldrich

  • (512125)  3-Pyridinylboronicacid  ≥95.0%

  • 1692-25-7

  • 512125-1G

  • 654.03CNY

  • Detail
  • Aldrich

  • (512125)  3-Pyridinylboronicacid  ≥95.0%

  • 1692-25-7

  • 512125-5G

  • 2,032.29CNY

  • Detail
  • Aldrich

  • (512125)  3-Pyridinylboronicacid  ≥95.0%

  • 1692-25-7

  • 512125-25G

  • 8,682.57CNY

  • Detail

1692-25-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Pyridylboronic acid

1.2 Other means of identification

Product number -
Other names 3-Pyridineboronic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1692-25-7 SDS

1692-25-7Synthetic route

3-Bromopyridine
626-55-1

3-Bromopyridine

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
Stage #1: 3-Bromopyridine; n-butyllithium In toluene at -50℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran at -50 - -15℃;
98%
3-Bromopyridine
626-55-1

3-Bromopyridine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
Stage #1: 3-Bromopyridine 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;
75%
Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexane; toluene at -50℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane; toluene at -50 - -15℃;
Stage #3: With sodium hydroxide In tetrahydrofuran; hexane; toluene
73%
With n-butyllithium; Triisopropyl borate In tetrahydrofuran at -78℃; for 3h;71%
3-Bromopyridine
626-55-1

3-Bromopyridine

Triisopropyl borate
5419-55-6

Triisopropyl borate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexanes; toluene at -60 - -50℃; for 0.75h;
Stage #2: Triisopropyl borate With hydrogenchloride In tetrahydrofuran; hexanes; water; toluene at -50 - -15℃;
73%
With n-butyllithium In tetrahydrofuran; hexane; toluene at -40℃; for 1.5h;
Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexane; toluene at -60 - -50℃; for 0.583333h;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane; toluene at -15℃;
pyridine
110-86-1

pyridine

Trimethyl borate
121-43-7

Trimethyl borate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
Stage #1: pyridine With lithium diisopropyl amide In diethyl ether at -78℃; for 1h;
Stage #2: Trimethyl borate In diethyl ether at 20℃; for 1h;
65%
lithium methanolate
865-34-9

lithium methanolate

4'-bromo-2,2':6',2''-terpyridine
149817-62-9

4'-bromo-2,2':6',2''-terpyridine

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane
201733-56-4

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

A

6′,6″-di(pyridin-2-yl)-2,2′:4′,4″:2″,2′′′-quaterpyridine
128143-86-2

6′,6″-di(pyridin-2-yl)-2,2′:4′,4″:2″,2′′′-quaterpyridine

B

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

C

4′-methoxy-2,2′:6′,2′′-terpyridine
181866-50-2

4′-methoxy-2,2′:6′,2′′-terpyridine

D

4'-((neopentyl glycolato)boron)-2,2':6',2''-terpyridine
381218-94-6

4'-((neopentyl glycolato)boron)-2,2':6',2''-terpyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In methanol at 55℃; for 18h;
diisopropyl 3-pyridylboronate

diisopropyl 3-pyridylboronate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; hexane; toluene at -20 - 20℃;
With hydrogenchloride at 0℃; pH=5 - 6;
With hydrogenchloride In tetrahydrofuran; hexane; water
With water; sodium hydroxide at 30℃; for 3h; Time; Temperature;
3-Bromopyridine
626-55-1

3-Bromopyridine

K4[Fe(CN)6]

K4[Fe(CN)6]

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: n-BuLi / tetrahydrofuran; hexane; toluene / -40 - -20 °C
2: aq. HCl / tetrahydrofuran; toluene; hexane / -20 - 20 °C
View Scheme
3-Bromopyridine
626-55-1

3-Bromopyridine

Trimethyl borate
121-43-7

Trimethyl borate

ethanol
64-17-5

ethanol

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
With n-butyllithium; acetic acid In diethyl ether; hexane; water
With n-butyllithium; acetic acid In diethyl ether; hexane; water
3-Bromopyridine
626-55-1

3-Bromopyridine

Trimethyl borate
121-43-7

Trimethyl borate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
3-Bromopyridine
626-55-1

3-Bromopyridine

Trimethyl borate
121-43-7

Trimethyl borate

tert.-butyl lithium
594-19-4

tert.-butyl lithium

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In methanol; diethyl ether; dichloromethane; pentane
With hydrogenchloride; sodium hydroxide In methanol; diethyl ether; dichloromethane; pentane
3-Bromopyridine
626-55-1

3-Bromopyridine

hydrogenchloride
7647-01-0

hydrogenchloride

Triisopropyl borate
5419-55-6

Triisopropyl borate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran (N2); addn. of 1.1 equiv. of butyllithium in hexanes to THF soln. of bromoarene deriv. at -78°C, stirring for 60-120 min at -78°C,addn. of 1.1 equiv. of borate deriv., warming to room temp. overnight; addn. of 2 M aq. HCl, extn (CH2Cl2), recrystn.;
C8H13Cl2N5

C8H13Cl2N5

4-fluoroaniline
371-40-4

4-fluoroaniline

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water; acetone at 20℃; for 16h;
pyridine-3-boronic acid dimethyl ester
175885-77-5

pyridine-3-boronic acid dimethyl ester

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
With hydrogenchloride In water at -15℃;
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
Stage #1: pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: tetrahydroxydiboron With potassium carbonate In water at 20℃; for 0.333333h;
3-iodopyridine
1120-90-7

3-iodopyridine

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
In methanol; water at -5℃; for 0.166667h; UV-irradiation; Flow reactor; chemoselective reaction;100 %Spectr.
Trimethyl borate
121-43-7

Trimethyl borate

pyridin-3-ylmagnesium bromide
21970-14-9

pyridin-3-ylmagnesium bromide

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

Conditions
ConditionsYield
at 10 - 20℃; for 0.5h;
2,6-dichloropyridine
2402-78-0

2,6-dichloropyridine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

N,N'-bis(3-pyridyl)-2,6-diaminopyridine
70650-96-3

N,N'-bis(3-pyridyl)-2,6-diaminopyridine

Conditions
ConditionsYield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;100%
2-Bromo-5-trifluoromethylaniline
454-79-5

2-Bromo-5-trifluoromethylaniline

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

2-(pyridin-3-yl)-5-(trifluoromethyl)benzeneamine
158461-54-2

2-(pyridin-3-yl)-5-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki cross-coupling; Inert atmosphere;100%
With sodium carbonate; trans-bis(triphenylphosphine)palladium dichloride In 1,4-dioxane; water for 24h; Suzuki cross-coupling; Heating;91%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 100℃; for 14h; Inert atmosphere;7.62 g
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; Inert atmosphere;
3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine
863783-61-3

3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

5,6-Dimethyl-3-(6-pyridin-3-yl-quinolin-4-yloxy)-[2,2']bipyridine

5,6-Dimethyl-3-(6-pyridin-3-yl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 3h;100%
3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine
863783-73-7

3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

5,6-Dimethyl-3-(7-pyridin-3-yl-quinolin-4-yloxy)-[2,2']bipyridine

5,6-Dimethyl-3-(7-pyridin-3-yl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 5h;100%
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

1-(3-Bromophenyl)ethanone
2142-63-4

1-(3-Bromophenyl)ethanone

3-(pyridin-3-yl)acetophenone
171092-38-9

3-(pyridin-3-yl)acetophenone

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; sodium carbonate In 2-methyltetrahydrofuran at 80℃; for 4h; Inert atmosphere;100%
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;90%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(3'-bromophenyl)pyridine
4422-32-6

3-(3'-bromophenyl)pyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 18h; Reflux;90.9%
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 18h; Inert atmosphere; Reflux;88%
1,3-dibromo-5-chlorobenzene
14862-52-3

1,3-dibromo-5-chlorobenzene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3,3’-(5-chloro-1,3-phenylene)dipyridine
1214345-76-2

3,3’-(5-chloro-1,3-phenylene)dipyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
2-bromo-4-methoxyaniline
32338-02-6

2-bromo-4-methoxyaniline

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(2-amino-5-methoxyphenyl)pyridine
923293-14-5

3-(2-amino-5-methoxyphenyl)pyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki cross-coupling; Inert atmosphere;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki coupling; Inert atmosphere;100%
3-iodo-1,8-dimethoxyanthracene-9,10-dione
1353384-15-2

3-iodo-1,8-dimethoxyanthracene-9,10-dione

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

1,8-dimethoxy-3-(pyridin-3'-yl)-anthraquinone
1353384-35-6

1,8-dimethoxy-3-(pyridin-3'-yl)-anthraquinone

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; Suzuki coupling; Inert atmosphere;100%
2-(8-Bromo-2-oxo-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-1(2H)-yl)-N-methyl-N-phenylacetamide

2-(8-Bromo-2-oxo-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-1(2H)-yl)-N-methyl-N-phenylacetamide

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

C24H22N4O2

C24H22N4O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 20℃; for 2.5h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;100%
5-(3-bromophenyl)-3-methoxy-5-(4-methoxyphenyl)pyrrolidin-2-one
1436712-97-8

5-(3-bromophenyl)-3-methoxy-5-(4-methoxyphenyl)pyrrolidin-2-one

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-methoxy-5-(4-methoxyphenyl)-5-(3-(pyridin-3-yl)phenyl)pyrrolidin-2-one
1436713-00-6

3-methoxy-5-(4-methoxyphenyl)-5-(3-(pyridin-3-yl)phenyl)pyrrolidin-2-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;100%
tert-butyl (5-bromo-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate
863724-27-0

tert-butyl (5-bromo-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

tert-butyl [2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]acetate

tert-butyl [2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]acetate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 20℃; for 2h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;100%
methyl 2-chloro-5-iodo-3-pyridinecarboxylate
78686-83-6

methyl 2-chloro-5-iodo-3-pyridinecarboxylate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

C12H9ClN2O2
1214383-62-6

C12H9ClN2O2

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 25℃; Suzuki Coupling;100%
3-Bromothiophene
872-31-1

3-Bromothiophene

potassium phosphate

potassium phosphate

bis(di-tert-butyl(3,5-di-(tert-butyl)phenyl)phosphine)dichloropalladium

bis(di-tert-butyl(3,5-di-(tert-butyl)phenyl)phosphine)dichloropalladium

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

butan-1-ol
71-36-3

butan-1-ol

3-(thiophen-3-yl)pyridine
21308-81-6

3-(thiophen-3-yl)pyridine

Conditions
ConditionsYield
In water100%
tert-butyl (2S)-2-[(S)-hydroxy{3-[(trifluoromethanesulfonyl)oxy]phenyl}methyl]piperidine-1-carboxylate
1007110-00-0

tert-butyl (2S)-2-[(S)-hydroxy{3-[(trifluoromethanesulfonyl)oxy]phenyl}methyl]piperidine-1-carboxylate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

tert-butyl (2S)-2-{(S)-hydroxy[3-(pyridin-3-yl)phenyl]-methyl}piperidine-1-carboxylate

tert-butyl (2S)-2-{(S)-hydroxy[3-(pyridin-3-yl)phenyl]-methyl}piperidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; N,N-dimethyl-formamide for 1.5h; Heating;100%
2-((trans-4-hydroxycyclohexyl)amino)-4-(4-iodo-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile

2-((trans-4-hydroxycyclohexyl)amino)-4-(4-iodo-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

2-((trans-4-hydroxycyclohexyl)amino)-4-(3-isopropyl-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile
1260536-06-8

2-((trans-4-hydroxycyclohexyl)amino)-4-(3-isopropyl-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
tert-butyl 3-(3-(3-bromophenyl)-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

tert-butyl 3-(3-(3-bromophenyl)-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

tert-butyl 3-(3-(3-(pyridin-3-yl)phenyl)-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

tert-butyl 3-(3-(3-(pyridin-3-yl)phenyl)-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 100℃; for 16h;100%
4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine
941685-08-1

4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

4-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

4-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water Inert atmosphere;99.9%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; for 5h; Inert atmosphere;99.9%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; for 5h; Inert atmosphere;99.9%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; for 5h; Inert atmosphere;99.9%
2-bromothiophene
1003-09-4

2-bromothiophene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-thiophen-2-yl-pyridine
21298-53-3

3-thiophen-2-yl-pyridine

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 90℃; for 1h; Suzuki coupling;62%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 24h; Suzuki-Miyaura coupling; Reflux;62%
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 120℃; for 12h; Reagent/catalyst; Time; Suzuki Coupling; Inert atmosphere;
bromobenzene
108-86-1

bromobenzene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 6h; Suzuki coupling; Inert atmosphere;99%
With C18H20Cl2N8Pd; caesium carbonate In 1,4-dioxane at 100℃; for 12h; Suzuki coupling; Inert atmosphere;96%
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;95%
4-n-butylchlorobenzene
15499-27-1

4-n-butylchlorobenzene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(4-n-butylphenyl)pyridine
732276-73-2

3-(4-n-butylphenyl)pyridine

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In butan-1-ol at 100℃; for 15h; Suzuki-Miyaura coupling;99%
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;93%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(p-methylphenyl)pyridine
90395-49-6

3-(p-methylphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 3h; Suzuki coupling; Inert atmosphere;99%
With C18H20Cl2N8Pd; caesium carbonate In 1,4-dioxane at 100℃; for 12h; Suzuki coupling; Inert atmosphere;91%
With potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki coupling reaction;85%
With potassium carbonate; [Pd(C3H5)Cl]2/Tedicyp complex In xylene at 130℃; for 20h; Suzuki reaction;85%
4-bromo-2-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-1-methoxybenzene
927384-45-0

4-bromo-2-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-1-methoxybenzene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-methoxy-1-(3-pyridyl)benzene

3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-methoxy-1-(3-pyridyl)benzene

Conditions
ConditionsYield
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane; water at 80℃; for 4h; Suzuki-Miyaura reaction;99%
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In not given at 60°C;99%
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol
841259-40-3

3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol

3-benzyloxy-4-(3-pyridyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

3-benzyloxy-4-(3-pyridyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 70℃; for 22h; Suzuki coupling;99%
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

4-bromo-aniline
106-40-1

4-bromo-aniline

4-pyridin-3-ylaniline
82261-42-5

4-pyridin-3-ylaniline

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;99%
With potassium phosphate tribasic heptahydrate In 1,4-dioxane for 48h; Suzuki coupling; Reflux;85%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water for 3.5h; Inert atmosphere;71%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;40%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;35%
3-bromo-2,6-dimethoxypyridine
13445-16-4

3-bromo-2,6-dimethoxypyridine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

2,6-dimethoxy-3-(3-pyridinyl)pyridine
1169827-10-4

2,6-dimethoxy-3-(3-pyridinyl)pyridine

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;99%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(3-methoxyphenyl)pyridine
4373-67-5

3-(3-methoxyphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 6h; Suzuki coupling; Inert atmosphere;99%
para-bromoacetophenone
99-90-1

para-bromoacetophenone

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

1-(4-(pyridin-3-yl)phenyl)ethan-1-one
90395-45-2

1-(4-(pyridin-3-yl)phenyl)ethan-1-one

Conditions
ConditionsYield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere;91.6%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere;91.6%
quinolin-8-yl methanesulfonate
916314-51-7

quinolin-8-yl methanesulfonate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

8-(3-pyridyl)-quinoline
37049-48-2

8-(3-pyridyl)-quinoline

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water at 95℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;99%
phenyl methanesulfonate
16156-59-5

phenyl methanesulfonate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water at 95℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;99%

1692-25-7Relevant articles and documents

A polyfluorene based zwitterionic fluorescent probe for response towards biological species in aqueous media

Chakraborty, Chanchal,Bera, Manas Kumar,Malik, Sudip

, p. 3522 - 3528 (2014)

Water soluble zwitterionic fluorescent conjugated boronic acid-bearing polyfluorene (PFBA) has been prepared from poly(9,9′-(6″-bromohexyl) fluorene-co-alt-1,4-phenylene) (polymer 3) through a post-polymerized quaternization with 3-pyridineboronic acid. Titration of diol containing monosaccharides (d-glucose and d-fructose), l-ascorbic acid and l-DOPA with PFBA polymer in 0.1 M phosphate buffer (pH 7.4) solution results in significant concentration dependent quenching of the blue fluorescence of the polymer due to static quenching as the bio-analytes form a ground state boronate ester complex with PFBA. Upon addition of d-glucose, the emission colour of PFBA changes to greenish-yellow owing to the effective induced aggregated polymer structure. PFBA also exhibits maximum response to the biological analytes at pH 7.4 which provides a scope for PFBA to be used in biological systems.

SYNTHESIS OF 5-(3-PYRIDYL)-2,2'-BITHIOPHENE(SENSITIZER)

-

Page/Page column 10-11, (2021/02/05)

Disclosed herein is a novel simple, short process for synthesis of the photosensitizer, 5-(3-pyridyl)-2,2'-bithiophene.

New compounds and organic light-emitting diode including the same

-

Paragraph 0200-0206; 0252; 0255-0258, (2019/08/30)

PURPOSE: A compound is provided to improve luminous efficiency and to make low voltage operation possible when applied to an organic electroluminescence device by having low driving voltage and excellent luminous efficiency. CONSTITUTION: A compound is represented by chemical formula 1. In chemical formula 1, each R is selected from hydrogen, deuterium, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C7-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C5-30 cycloalkenyl, substituted or unsubstituted C1-30 alkoxy, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C1-30 alkylthioxy, substituted or unsubstituted C5-30 arylthioxy, substituted or unsubstituted C1-30 alkylamine, substituted or unsubstituted C5-30 arylamine, substituted or unsubstituted C5-50 aryl, substituted or unsubstituted C3-50 heteroaryl, substituted or unsubstituted silicon, substituted or unsubstituted boron, substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, hydroxy, nitro, halogen, amide, and ester.

Preparation method of mono-heterocyclic boric acid

-

Paragraph 0050; 0052; 0067; 0069; 0071; 0073; 0075, (2018/09/13)

The invention provides a preparation method of mono-heterocyclic boric acid. The preparation method comprises steps as follows: (1) a compound shown in a formula I and alkyl borate are dissolved in asolvent A, and a liquor A is obtained; an organic lithium reagent is dissolved in a solvent B, and a liquor B is obtained; the liquor A and the liquor B are subjected to a continuous feeding reaction,the reaction is ended after a product flows out of a reaction pipe, and an intermediate is obtained; (2) the intermediate obtained in the step (1) is subjected to a hydrolysis reaction, and mono-heterocyclic boric acid is obtained. According to the provided preparation method, the reaction yield can be increased and can be up to 95% or above, the reaction time is shortened, the reaction can be completed within 5-60 min, the reaction temperature can be increased, energy consumption of the low-temperature reaction is reduced, the temperature is controllable, the safety is improved, the pressureis convenient to control, the automation degree is improved, production operation is facilitated, the cost is reduced, and the economic benefits are improved.

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