3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical Properties

Melting point:

102-104.4 °C(lit.)

Boiling point:

300.9±15.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Acetone

pka

5.22±0.12(Predicted)

form 

Crystalline Powder

color 

White

Water Solubility 

Insoluble

InChI

InChI=1S/C11H16BNO2/c1-10(2)11(3,4)15-12(14-10)9-6-5-7-13-8-9/h5-8H,1-4H3

InChIKey

XEMDFESAXKSEGI-UHFFFAOYSA-N

SMILES

C1=NC=CC=C1B1OC(C)(C)C(C)(C)O1

CAS DataBase Reference

329214-79-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

3-Pyridineboronic Acid Pinacol Ester is an organoborane compound used in the preparation of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol Ester is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.

Uses

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is an organoborane compound used in the preparation of of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol E ster is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.

Synthesis

In a nitrogen-protected glove box, a benzene solution of silica-3p-TPP ([P] content 0.11 mmol/g, 45.5 mg, 0.005 mmol P, 1 mol% P), anhydrous degassed benzene (0.8 mL), and [PdCl(η3-cinnamyl)]2 (0.65 mg, 0.00125 mmol, 0.5 mol% Pd) (0.2 mL) was added sequentially to an oven-dried 10 mL glass tube pre-fitted with a magnetic stirrer. After stirring for 5 min, KOAc (147 mg, 1.5 mmol), bis(pinacolato)diboron (2,140 mg, 0.55 mmol) and 3-chloropyridine (63.3 mg, 0.50 mmol) were added sequentially. The reaction tube was sealed with a screw cap and then removed from the glove box, and the reaction was stirred at 25°C for 10 hours. After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad (eluting with Et2O) and the filtrate was concentrated under reduced pressure. To the residue was added the internal standard 1,1,2,2-tetrachloroethane, and the yield of the product 3-pyridineboronic acid pinacol ester was 95% as determined by 1H NMR. The crude product was purified by silica gel column chromatography to afford the target compound 3-pyridineboronic acid pinacol ester (87.0 mg, 0.40 mmol, 80% yield).

References

[1] ChemCatChem, 2014, vol. 6, # 5, p. 1340 - 1348
[2] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5359 - 5363
[4] Chemistry Letters, 2014, vol. 43, # 5, p. 584 - 586
[5] Patent: WO2010/110782, 2010, A1. Location in patent: Page/Page column 46-47

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine(329214-79-1)Related Product Information

• 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE,4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 4-Pyridylboronic acid pinacol ester
• 3-Pyridylboronic acid
• Pyridine-4-boronic acid
• ISONICOTINOYL CHLORIDE HYDROCHLORIDE
• 3-Amino-5-bromopyridine
• 6-(Morpholin-4-yl)pyridine-3-boronic acid pinacol ester
• 2-METHOXYPYRIDINE-5-BORONIC ACID PINACOL ESTER
• 4-Isoquinolineboronic acid pinacol ester
• 2-(2-Chloro-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine
• 4-[5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 2,2-DIMETHYL-N-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YL]-PROPIONAMIDE
• 2-Aminopyridine-5-boronic acid, pinacol ester
• 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• 2-CHLORO-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2,6-DIMETHOXY-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 3-CHLORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• 5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine,3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
• 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE