2-PHENOXYPHENYLBORONIC ACID Chemical Properties

Melting point:

104-108 °C (lit.)

Boiling point:

369℃

Density 

1.23

Flash point:

177℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Powder or Crystalline Powder

pka

8.44±0.58(Predicted)

color 

White to off-white

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

108238-09-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2931900090

MSDS

• Language:English Provider:SigmaAldrich

2-PHENOXYPHENYLBORONIC ACID Usage And Synthesis

Uses

suzuki reaction

Uses

Reactant for palladium catalyzed cross-coupling reactions, trifluoromethylation via copper-mediated oxidative cross-coupling, preparation of biologically and pharmacologically active molecules, preparation of pyridazine-based scaffolds as a-helix mimetics.

Synthesis

The general procedure for the synthesis of 2-phenoxyphenylboronic acid from triisopropyl borate and 2-bromobiphenyl ether was as follows: 1-bromo-2-phenoxybenzene (0.018 mmol) was dissolved in 100 mL of anhydrous THF and added to an undried 500 mL triple-necked flask. The reaction system was cooled to -78 °C under nitrogen protection and maintained at this temperature for 30 min. Subsequently, n-butyllithium (0.027 mmol) was slowly added dropwise, and after the drop was completed, the reaction was maintained at -78 °C for 3 hours. Next, triisopropyl borate (0.02 mmol) was added dropwise slowly, and after the dropwise addition was completed, the reaction was continued at -78 °C for 2 hours. After that, the reaction was slowly warmed up to room temperature and reacted overnight. The progress of the reaction was monitored by TLC and after confirming the completion of the reaction, the reaction solution was quenched slowly by the addition of water, followed by extraction to dryness to give 2-phenoxyphenylboronic acid (B-1) (0.0144 mmol) in 80% yield. Mass spectral data: 214.06.

References

[1] Patent: CN106565434, 2017, A. Location in patent: Paragraph 0128-0131

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