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2-Cyanopyridine-5-boronic acid pinacol ester
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Name

2-Cyanopyridine-5-boronic acid pinacol ester

 EINECS N/A
CAS No. 741709-63-7 Density 1.1 g/cm3
PSA 55.14000 LogP 1.25248
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 N/A Appearance N/A
Safety 26-39 Risk Codes 37/38-41
Molecular Structure Molecular Structure of 741709-63-7 (2-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER) 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;

Article Data 8

2-Cyanopyridine-5-boronic acid pinacol ester 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 1.25h;73%

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

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