3-Quinolineboronic acid Chemical Properties

Melting point:

148-155°C

Boiling point:

400.3±37.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

4.61±0.30(Predicted)

color 

Light pink or orange to light brown

BRN 

8764547

InChI

InChI=1S/C9H8BNO2/c12-10(13)8-5-7-3-1-2-4-9(7)11-6-8/h1-6,12-13H

InChIKey

YGDICLRMNDWZAK-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C=C(B(O)O)C=1

CAS DataBase Reference

191162-39-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

36/37/39-26-22-37-36

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29334900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Quinolineboronic acid Usage And Synthesis

Chemical Properties

light pink or orange to light brown powder

Uses

May contain varying amounts of anhydride.

Uses

3-Quinolineboronic acid is a member of a group of boronic acid derivatives that change fluorescence properties once they are bound to sugar molecules. 3-Quinolineboronic acid is also a potential inhibitor of the Staphylococcus aureus NorA efflux pump.

Uses

3-Quinolineboronic acid can be used as a reactant for: Preparation of P1-substituted symmetry-based human immunodeficiency virus protease inhibitors with antiviral activity against drug-resistant viruses Preparation of heterobiaryls via Suzuki-Miyaura cross-coupling with heteroaryl halides in co

General Description

May contain varying amounts of anhydride

Synthesis

General procedure for the synthesis of quinoline-3-boronic acid from 3-bromoquinoline: triisopropyl borate (3.30 mL, 29.06 mmol) and 3-bromoquinoline (3.00 g, 14.49 mmol) were added to a 250 mL two-necked round-bottomed flask under nitrogen protection and dissolved in anhydrous tetrahydrofuran (100 mL). The reaction system was cooled to -78 °C and a 2M hexane solution of n-butyllithium (14.50 mL, 29.00 mmol) was slowly added dropwise through a dropping funnel over a controlled period of 1 hour. After the dropwise addition, the reaction was kept at -78 °C for 2 hours. Subsequently, the acetone/dry ice bath was removed and the reaction system was slowly warmed to 0 °C. The reaction was quenched with 2 M hydrochloric acid solution, followed by adjusting the pH with 2 M sodium bicarbonate solution to 7. The reaction mixture was extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure. The product was precipitated by addition of hexane to give a white solid in 80% yield.

References

[1] Dyes and Pigments, 2013, vol. 99, # 1, p. 105 - 115
[2] Synthetic Communications, 2003, vol. 33, # 5, p. 795 - 800
[3] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[4] Patent: US2009/181941, 2009, A1. Location in patent: Page/Page column 49-50
[5] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673

3-Quinolineboronic acid(191162-39-7)Related Product Information

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