2-CHLOROPYRIMIDINE-5-BORONIC ACID Chemical Properties

Boiling point:

425.4±37.0 °C(Predicted)

Density 

1.52±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

5.03±0.11(Predicted)

form 

Powder

color 

White

InChI

InChI=1S/C4H4BClN2O2/c6-4-7-1-3(2-8-4)5(9)10/h1-2,9-10H

InChIKey

YTCIHPTZKKWKKC-UHFFFAOYSA-N

SMILES

B(C1=CN=C(Cl)N=C1)(O)O

CAS DataBase Reference

1003845-06-4

Safety Information

HS Code 

2933599590

2-CHLOROPYRIMIDINE-5-BORONIC ACID Usage And Synthesis

Uses

2-Chloropyrimidine-5-boronic acid is a pyrimidine-boronic acid compound, mainly used as a raw material for organic synthesis or a reagent for chemical reactions.

Synthesis

Step 1: Synthesis of 2-chloropyrimidin-5-ylboronic acid Under argon protection, 5-bromo-2-chloropyrimidine (1.0 g, 5.170 mmol) was dissolved in a solvent mixture of THF and toluene (25 mL, 4:1 v/v), and cooled to -78 °C. n-Butyllithium (1.6 M hexane solution, 3.87 mL, 5.61 mmol) was slowly added dropwise at -78 °C, and the reaction was kept at -78 °C for 4 hours after completion of the dropwise addition. After completion of the reaction, the reaction mixture was diluted with ice water, returned to room temperature and stirred for 1 hour. Subsequently, the aqueous phase was extracted with ether and the organic phase was combined. The aqueous phase was acidified to pH 2-3 with 1N hydrochloric acid and extracted with ethyl acetate. All organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 2-chloropyrimidin-5-ylboronic acid (0.6 g, 73.3% yield) as a white solid. Mass spectrum (MS): 159.3 [M+H]+.

References

[1] Patent: US2017/291910, 2017, A1. Location in patent: Paragraph 0508-0510
[2] Patent: WO2008/9435, 2008, A1. Location in patent: Page/Page column 189-190
[3] Patent: WO2011/84402, 2011, A1. Location in patent: Page/Page column 153

2-CHLOROPYRIMIDINE-5-BORONIC ACID(1003845-06-4)Related Product Information

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