2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE Chemical Properties

Melting point:

117-119°C

Boiling point:

373.2±42.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

-3.74±0.10(Predicted)

color 

White to Almost white

InChIKey

PEFDHAOFDBNZEQ-UHFFFAOYSA-N

CAS DataBase Reference

408492-27-3

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2933399990

2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE Usage And Synthesis

Uses

2,6-Dichloropyridine-4-boronic acid, pinacol ester

Synthesis

General procedure for the synthesis of 2,6-dichloropyridine-4-boronic acid pinacol ester from 2,6-dichloropyridine and bis-boronic acid pinacol ester: Under nitrogen protection, 2,6-dichloropyridine (3 g, 20.3 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl (5.92 g, 23.3 mmol), 1,10-phenanthroline (145 mg, 0.81 mmol) and chlorobis(1,5-cyclooctadiene)iridium(I) dimer (267 mg, 0.30 mmol) were dissolved in 1,2-dichloroethane (20 mL). After passing nitrogen for 5 minutes, the reaction mixture was heated at 100 °C for 1 hour. Upon completion of the reaction, the cooled mixture was poured into a mixture of ether (150 mL) and 4 M aqueous sodium hydroxide (200 mL) to separate the organic and aqueous phases. The aqueous phase was cooled with an ice bath and acidified with 5 M aqueous hydrochloric acid, and the resulting precipitate was filtered, washed with water and dried to afford 2,6-dichloropyridine-4-boronic acid pinacol ester (4.9 g, 17.9 mmol, 88% yield).LCMS (Method A): retention time 0.74 min; m/z 192,194 (as MH+ for boronic acid ionization).1H NMR ( 400 MHz, DMSO-d6) δ 1.28 (12H, s), 7.57 (2H, s).

References

[1] Organic Letters, 2009, vol. 11, # 16, p. 3586 - 3589
[2] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8058 - 8061
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
[4] Patent: WO2011/110575, 2011, A1. Location in patent: Page/Page column 73
[5] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202

2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE(408492-27-3)Related Product Information

• 2,6-Dichloropyridine-4-boronicacid
• 2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2-Chloropyridine-4-boronic acid pinacol ester