2-CHLOROQUINOLINE-3-BORONIC ACID Chemical Properties

Melting point:

144-147℃

Boiling point:

426.2±55.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

5.62±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H7BClNO2/c11-9-7(10(13)14)5-6-3-1-2-4-8(6)12-9/h1-5,13-14H

InChIKey

JAQXYUOPSOXQCG-UHFFFAOYSA-N

SMILES

B(C1=CC2C(N=C1Cl)=CC=CC=2)(O)O

CAS DataBase Reference

128676-84-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933499090

MSDS

• Language:English Provider:ALFA

2-CHLOROQUINOLINE-3-BORONIC ACID Usage And Synthesis

Uses

2-Chloroquinoline-3-Boronic acid can be converted to 2-chloro-3-hydroxyquinoline in 98% yield by oxidizing with ammonium chloride in aqueous solution with peroxide. Further hydrolysis of 2-chloro-3-hydroxyquinoline yields 3-hydroxy-2-quinolinone.

Synthesis

2-Chloroquinoline was lithiated with lithium diisopropylamide in a low-temperature tetrahydrofuran solution, followed by the addition of trimethylborate ester, and finally acidification to obtain 2-Chloroquinoline-3-boronic acid in 85% yield.

References

[1] Marsais, F., Godard, A., & Queguiner, G. (1989). Directed ortho-lithiation of chloroquinolines. Application to synthesis of 2,3-disubstituted quinolines. Journal of Heterocyclic Chemistry, 26 6, 1589–1594. https://doi.org/10.1002/jhet.5570260615

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