9-phenanthrenylboronic acid Chemical Properties

Melting point:

165-170 °C

Boiling point:

479.5±28.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in DMSO.

pka

8.53±0.30(Predicted)

form 

Solid

color 

Pale Yellow

InChI

InChI=1S/C14H11BO2/c16-15(17)14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,16-17H

InChIKey

JCDAUYWOHOLVMH-UHFFFAOYSA-N

SMILES

B(C1=CC2C(C3C1=CC=CC=3)=CC=CC=2)(O)O

CAS DataBase Reference

68572-87-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

9-phenanthrenylboronic acid Usage And Synthesis

Chemical Properties

White solid

Uses

9-Phenanthreneboronic Acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection.

Uses

9-Phenanthracenylboronic acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection and in suzuki reaction.

Synthesis

The general procedure for the synthesis of 9-phenanthrenylboronic acid from triisopropyl borate and 9-bromophenanthrene is as follows: Step a: Preparation of 9-phenanthracenylboronic acid Under argon protection, 9-bromophenanthrene (1 g, 3.9 mmol) and triisopropyl borate (1.35 ml, 1.1 g, 5.85 mmol) were dissolved in anhydrous THF (30 ml) and the solution was cooled to -78 °C. Subsequently, n-BuLi (1.6 M hexane solution, 2.9 ml, 4.68 mmol) was added slowly dropwise over 1 h. The reaction temperature was maintained at -78 °C and stirring was continued for 1 h. The reaction mixture was then cooled to -78 °C. The reaction temperature was then adjusted to -78 °C. After that, the reaction mixture was slowly warmed up to -20°C, 2M HCl (20 ml) was added, and the temperature was continued to 18°C and stirring was continued for 1 hour. After completion of the reaction, ether (300 ml) was added for extraction, the organic phase was dried with MgSO4, filtered and concentrated under reduced pressure to afford the crude product 9-phenanthrenylboronic acid (770 mg, 89% yield) as a white solid, which can be used in subsequent reactions without further purification.

References

[1] Patent: WO2006/135973, 2006, A1. Location in patent: Page/Page column 31
[2] Patent: CN107652224, 2018, A. Location in patent: Paragraph 0086; 0089-0091
[3] Patent: CN107382748, 2017, A. Location in patent: Paragraph 0037; 0038; 0039; 0040

9-phenanthrenylboronic acid(68572-87-2)Related Product Information

• Boric acid
• Citric acid
• 9-Anthraceneboronic acid
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Zinc borate
• Phenanthrene
• Glycine
• Fluoroboric acid
• Stearic acid
• Ascoric Acid
• 1-Naphthylboronic acid
• 2-Naphthaleneboronic acid
• Methylboronic acid
• Phenylboronic acid
• 9-phenanthrenylboronic acid
• phosphoric acid