2-Formylbenzeneboronic acid Chemical Properties

Melting point:

115-120 °C (lit.)

Boiling point:

355.7±44.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in methanol.

form 

Crystalline Powder or Needles and Chunks

pka

8.18±0.53(Predicted)

color 

Light yellow to light orange-pink

Sensitive 

Air Sensitive

BRN 

3030776

InChIKey

DGUWACLYDSWXRZ-UHFFFAOYSA-N

CAS DataBase Reference

40138-16-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Formylbenzeneboronic acid Usage And Synthesis

Chemical Properties

light yellow to light orange-pink crystalline

Uses

suzuki reaction

Uses

2-Formylbenzeneboronic acid is used as an organic chemical synthesis intermediate.

Synthesis

Under nitrogen protection, o-bromophenylboronic acid trimer (cas:1229227-01-3) was added to anhydrous tetrahydrofuran (600 mL). The mixture was transferred to a 2 L three-neck flask and N,N-dimethylformamide (87.7 g, 1.2 mol) was added. Subsequently, the reaction system was cooled to -70 °C to -80 °C and 2.5 M n-butyllithium hexane solution (520 mL, 1.3 mol) was slowly added dropwise with controlled titration rate to keep the reaction temperature from exceeding -70 °C. Stirring was continued at this temperature for 1-3 h. The reaction mixture was then allowed to warm up to room temperature naturally, and stirring was continued for another 3-5 h. The reaction was monitored by TLC. The progress of the reaction was monitored by TLC and after confirming the completion of the reaction, the system was cooled to 0°C, 15% aqueous hydrochloric acid was added to quench the reaction, and the pH was adjusted to 1-2. Stirring was continued at room temperature for 3-5 h to ensure complete hydrolysis of the trimer. Subsequently, the reaction solution was distilled to remove the organic solvent and filtered to obtain the solid product. Finally, purification by recrystallization from toluene gave 93.0 g of light gray solid 2-formylphenylboronic acid with 99.0% HPLC purity and 62% yield.

References

[1] Patent: CN105037408, 2017, B. Location in patent: Paragraph 0028; 0031; 0032

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