2-Cyanopyridine-5-boronic acid pinacol ester supplier

Name
2-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER
EINECS
CAS No. 741709-63-7
Article Data8
CAS DataBase
Density 1.1 g/cm³
Solubility Slightly soluble in water.
Melting Point 105-106℃
Formula C₁₂H₁₅BN₂O₂
Boiling Point 370.7 °C at 760 mmHg
Molecular Weight 230.074
Flash Point 178 °C
Transport Information
Appearance
Safety 26-39
Risk Codes 37/38-41
Molecular Structure
Hazard Symbols Xi
Synonyms (2-Cyanopyridin-5-yl)boronicacid pinacol ester;2-Cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine-2-carbonitrile;
PSA 55.14000
LogP 1.25248

Synthetic route

: 97483-77-7
2-Cyano-5-bromopyridine

: 73183-34-3
bis(pinacol)diborane

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

Conditions

Conditions	Yield
With potassium acetate; palladium dichloride In dichloromethane; dimethyl sulfoxide at 90℃; for 6h;	85%
With triisopropylsilanethiol; N,N,N',N'-tetramethylguanidine In acetonitrile at 30℃; for 2h; Reagent/catalyst; Irradiation; Inert atmosphere; Sealed tube;	68%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 25h;	64%

: 31181-90-5
5-bromo-pyridine-2-carbaldehyde

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / I2; aq. NH3 / tetrahydrofuran / 4 h / 20 °C 2: 64 percent / PdCl2(dppf); KOAc / dimethylsulfoxide / 25 h / 80 °C View Scheme

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 880495-82-9
C-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methylamine

Conditions

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal at 20℃; for 16h;	100%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: tert-butyl [(1S)-1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate

: tert-butyl {(1S)-1-[5-chloro-3-(6-cyanopyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In acetonitrile at 95℃; for 2h; Inert atmosphere;	91%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: tert-butyl (((3S,3aS)-7-bromo-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

: tert-butyl (((3S,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; dimethyl sulfoxide at 100℃; for 5h; Inert atmosphere;	89%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 954123-89-8
tert-butyl 4-((5-bromo-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

: 954123-95-6
tert-butyl 4-((5-(6-cyanopyridin-3-yl)-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

Conditions

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 120℃; for 1h; Sealed tube; Microwave irradiation;	88%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: tert-butyl (((3S,3aS)-7-bromo-6-fluoro-1-oxo-3,3a-dihydro-1H,9hbenzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

: tert-butyl (((3S,3aS)-7-(6-cyanopyridin-3-yl)-6-fluoro-1-oxo-3,3a-dihydro-1H,9H-benzo[e]oxazolo[4,3-b][1,3]oxazin-3-yl)methyl)carbamate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; dimethyl sulfoxide at 100℃; for 5h; Inert atmosphere;	88%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 32779-36-5
5-Bromo-2-chloropyrimidine

: 951657-94-6
2,5-bis-(2'-cyanopyridin-5'-yl)-pyrimidine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene at 80℃; Suzuki coupling; Inert atmosphere;	78%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 7-tert-butoxycarbonyl-2-exo-(2′-amino-3′-bromo-5′-pyridinyl)-7-azabicyclo[2.2.1]heptane

: 7-tert-butoxycarbonyl-2-exo-[2'-amino-3'-(6-cyanopyridin-3-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane

Conditions

Conditions	Yield
With sodium carbonate; tris-(o-tolyl)phosphine; palladium diacetate In 1,2-dimethoxyethane; water at 80℃; for 5h; Suzuki coupling;	74%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 1155287-84-5
6-bromomethyl-4-(3-chloro-phenyl)-5-fluoro-benzothiazole

: 1155286-87-5
5-[4-(3-chloro-phenyl)-5-fluoro-benzothiazol-6-ylmethyl]-pyridine-2-carbonitrile

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 1.25h;	73%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 281225-12-5
(6S)-6-[(4-iodobenzyl)oxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

: 1257425-59-4
5-[4-({[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)phenyl]-2-pyridinecarbonitrile

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol; water; toluene for 0.666667h; Suzuki coupling; Inert atmosphere; Reflux;	73%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 6630-33-7
ortho-bromobenzaldehyde

: 1033804-84-0
5-(2-formylphenyl)pyridine-2-carbonitrile

Conditions

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 100℃; for 0.166667h; Microwave irradiation;	72%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 100℃; for 0.166667h; Microwave irradiation; Sealed tube;	72%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 1160789-92-3
1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea

: 1160790-79-3
1-(5-(6-cyanopyridin-3-yl)-6-fluorobenzo[d]thiazol-2-yl)-3-ethylurea

Conditions

Conditions	Yield
Stage #1: 2-cyanopyridine-5-boronic acid pinacol ester; 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h; Stage #2: bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 100℃; for 2.25h;	71%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 1382996-38-4
1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol

: 1426699-27-5
5-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 95℃; for 2h; Inert atmosphere;	70%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 95℃; for 2h; Inert atmosphere;	70%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 217435-65-9
6-bromo-8-methylimidazo[1,2-a]pyridine

: 1611001-20-7
5-(8-methylimidazo[1,2-a]pyridin-6-yl)picolinonitrile

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	68.5%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 1214908-78-7
C18H17BrF2N4O

: 1214909-17-7
C24H20F2N6O

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 150℃; for 0.5h; Inert atmosphere; microwave oven;	68%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 1417334-55-4
6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine

: 1611002-02-8
5-(8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl)picolinonitrile

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	67.8%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: N-{[(3S,3aS)-7-bromo-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

: 1341208-63-6
N-(((3S,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)acetamide

Conditions

Conditions	Yield
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 2h; Suzuki coupling;	65%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 930595-71-4
C28H50IN5O4Si2

: 930596-22-8
C34H53N7O4Si2

Conditions

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane; water for 3h; Heating / reflux;	63%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl trifluoromethanesulfonate

: 5-((3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl)picolinonitrile

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium acetate; palladium diacetate In ethanol; toluene at 80℃; for 48h; Inert atmosphere;	63%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 1575607-48-5
(2R, 3R)-3-(3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

: 1575607-70-3
(2R,3R)-3-(3-(2-cyano-pyridin-5-yl)-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)-2-(2,4-difluoro-phenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 12h;	61.6%

: 741709-63-7
2-cyanopyridine-5-boronic acid pinacol ester

: 2-bromo-5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5,6-dihydro-4H-thieno[3,2-c]pyrrol-4-one

: 5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-2-(2-cyanopyridin-5-yl)-5,6-dihydro-4H-thieno[3,2-c]pyrrol-4-one

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 10h; Suzuki Coupling; Inert atmosphere;	61.6%

2-Cyanopyridine-5-boronic acid pinacol ester Specification

This chemical is called 2-Pyridinecarbonitrile,5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, and its systematic name is 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile. With the molecular formula of C₁₂H₁₅BN₂O₂, its molecular weight is 230.07. The CAS registry number of this chemical is 741709-63-7. Additionally, its product categories are Boronic Ester; Organo Borons; Pyridine.

Other characteristics of the 2-Pyridinecarbonitrile,5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- can be summarised as followings: (1)#H bond acceptors: 4; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 55.14 Å²; (5)Index of Refraction: 1.506; (6)Molar Refractivity: 61.82 cm³; (7)Molar Volume: 207.8 cm³; (8)Polarizability: 24.5×10^-24cm³; (9)Surface Tension: 40.7 dyne/cm; (10)Density: 1.1 g/cm³; (11)Flash Point: 178 °C; (12)Enthalpy of Vaporization: 61.76 kJ/mol; (13)Boiling Point: 370.7 °C at 760 mmHg; (14)Vapour Pressure: 1.09E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: N#Cc2ncc(B1OC(C)(C)C(O1)(C)C)cc2
2.InChI: InChI=1/C12H15BN2O2/c1-11(2)12(3,4)17-13(16-11)9-5-6-10(7-14)15-8-9/h5-6,8H,1-4H3
3.InChIKey: IXTBQKLZPOYJFJ-UHFFFAOYAI

Product Name

2-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER

Synthetic route

2-Cyanopyridine-5-boronic acid pinacol ester Specification

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