2-Carboxyphenylboronic acid Chemical Properties

Melting point:

138-141°C

Boiling point:

412.3±47.0 °C(Predicted)

Density 

1.40±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.27±0.36(Predicted)

color 

White to Almost white

BRN 

2835407

InChIKey

KWNPRVWFJOSGMZ-UHFFFAOYSA-N

CAS DataBase Reference

149105-19-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22-36/37

Safety Statements 

26-36/37/39-36

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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2-Carboxyphenylboronic acid Usage And Synthesis

Chemical Properties

White powder

Uses

2-Carboxyphenylboronic acid is used in the studies on a new class of carbohydrate-binding boronic acids called the boronophthalide; a sugar-binding boronic acids that is soluble and capable of complexing glycosides in neutral water.

Synthesis

The o-bromophenylboronic acid trimer was dissolved in 600 mL of anhydrous tetrahydrofuran under nitrogen protection. After homogenization, the solution was transferred to a 2 L three-neck flask and cooled to -10 °C. Under the condition of maintaining temperature, 1.2 L of 1 M isopropylmagnesium chloride solution (1.2 moles) was added slowly and dropwise. After the dropwise addition, the reaction was continued to be stirred at -10 °C for 1-3 hours. Subsequently, the reaction system was allowed to warm up naturally to room temperature and stirring was continued for 2-5 hours. The reaction system was cooled to 0 °C again, dry ice was added in three batches, the reaction was stirred and the reaction progress was monitored by TLC. Upon completion of the reaction, the reaction was quenched with 15% aqueous hydrochloric acid, the pH was adjusted to 1-2, and stirring was continued for 3-5 hours at room temperature to ensure complete hydrolysis of the trimer. After precipitation of the solid, it was filtered and recrystallized from a mixed solvent of water and ethanol to give 81.4 g of white solid o-carboxyphenylboronic acid with HPLC purity of 98.4%. The overall yield of the two-step reaction was 49%.

References

[1] Patent: CN104844643, 2017, B. Location in patent: Paragraph 0032; 0033

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