5-Bromopyridine-3-boronic acid Chemical Properties

Melting point:

>300°C

Boiling point:

351.5±52.0 °C(Predicted)

Density 

1.78±0.1 g/cm3(Predicted)

storage temp. 

Keep Cold

form 

solid

pka

5.91±0.10(Predicted)

color 

off white

BRN 

9119873

CAS DataBase Reference

452972-09-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

5-Bromopyridine-3-boronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Reactant for preparation of:• ;Thienylpyridyl garlands via cross-coupling with heteroaryl halides1• ;Arenes via nickel-catalyzed cross-coupling with potassium aryl- and heteroaryl trifluoroborates2• ;Meso-substituted ABCD-type porphyrins by functionalization reactions3• ;Analogs of (acetylamino)(dimethylpyrazol)(pyridyl)pyrimidines as A2A adenosine receptor antagonists for the treatment of Parkinson′s disease4• ;5-hydroxy-1,3,2-dioxaborolan-4-ones boronate-amine complexes via heterocyclization with α-oxocarboxylic acids followed by subsequent complexation5&

Synthesis

Steps for the synthesis of 3-bromo-5-pyridineboronic acid (2b): 3-bromo-5-fluoropyridine (2a) (25 kg, 142 moles, 1.0 eq.), THF (222.5 kg), and isopropyl borate (28 kg, 149.3 moles, 1.05 eq.) were added to a 700 L cryoreactor. The mixture was cooled to -90°C to -80°C and stirred. Subsequently, n-BuLi (40.2 kg, 2.5 M, 142 mol, 1.0 eq.) was added dropwise at a rate of 2 kg/h while ensuring that the temperature was below -87°C. After the dropwise addition, stirring of the reaction mixture was continued for 2.5 h at -88 °C to -83 °C. After confirming the completion of the reaction by HPLC analysis, the reaction was quenched by the addition of 9% HCl aqueous solution (7.7 kg). The mixture was transferred to a 1000 L glass-lined reactor and warmed to -20°C to -10°C. Next, additional HCl solution (122.3 kg) was added to adjust the pH to 1-2, during which the temperature was maintained at 0-10°C. It was allowed to stand for 0.5 h to stratify, the organic layer was separated and washed with saturated brine (38 kg). After stirring again for 0.5 h, the mixture was left to stratify for 0.5 h. The aqueous layer was separated. The aqueous layer was separated and the combined aqueous layers were extracted twice with EtOAc (51kg and 25kg). The organic phases were combined and the pH was adjusted to 6 with 30% NaOH aqueous solution (27.4 kg), at which point solids precipitated. The slurry was filtered by centrifugation and the solids were dried in a disk drier at 40-45 °C to give 3-bromo-5-pyridineboronic acid (2b) as a white solid (17.5 kg, 87.4% yield, 98.6% purity AUC, method of use B).

References

[1] Patent: WO2009/76200, 2009, A2. Location in patent: Page/Page column 54-55

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