2-Bromopyridine-5-boronic acid Chemical Properties

Melting point:

161-166 °C

Boiling point:

358.2±52.0 °C(Predicted)

Density 

1.78±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

pka

6.62±0.10(Predicted)

form 

solid

color 

white to off-white

BRN 

9119918

CAS DataBase Reference

223463-14-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

RIDADR 

2811

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Bromopyridine-5-boronic acid Usage And Synthesis

Chemical Properties

Off-white solid

Uses

Reactant involved in:

• Iterative cross-coupling reactions for synthesis of non-cytotoxic terpyridines
• The Garlanding approach for synthesis of phenyl-pyridyl scaffolds
• Cyanation for synthesis of aromatic nitriles
• Suzuki-Miyaura cross-coupling with dihalopyridines and dihalobipyridines
• Petasis boronic Mannich reaction

General Description

May contain varying amounts of anhydride

Synthesis

General procedure for the synthesis of 2-bromopyridine-5-boronic acid from 2,5-dibromopyridine and triisopropyl borate: 1. 2,5-dibromopyridine (2.37 g, 10 mmol) was dissolved in 90 mL of ether/THF (8:1) at -78 °C and 7.5 mL of n-BuLi (1.6 M hexane solution) was added dropwise slowly. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -78°C for 2 hours. 2. Triisopropyl borate (4.49 g, 24 mmol) was added and the reaction mixture was stirred at -78 °C for 2 h, followed by slow warming to room temperature. 3. The reaction was quenched with 10 mL of water and stirring was continued overnight. 4. The organic solvent was evaporated and the remaining aqueous layer was adjusted to pH 10 with 5% NaOH and washed with ether (30 mL x 3). 5. The aqueous layer was carefully acidified to pH 4 with 48% HBr to precipitate the target product 2-bromopyridine-5-boronic acid (1.46 g, 72%). NMR data (300 MHz, DMSO-d6): δ 8.68 (dd, J = 2.1, 0.7 Hz, 1H), 8.53 (br.s, 2H), 8.05 (dd, J = 2.1, 7.8 Hz, 1H), 7.67 (dd, J = 7.8, 0.7 Hz, 1H).

References

[1] Patent: WO2012/125832, 2012, A2. Location in patent: Page/Page column 80

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