3-Formylphenylboronic acid Chemical Properties

Melting point:

109-113 °C

Boiling point:

354.4±44.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Methanol

pka

7.83±0.10(Predicted)

form 

Powder, Crystals, and/or Chunks

color 

Off-white to beige or light orange

Sensitive 

Air Sensitive

BRN 

3030769

InChI

InChI=1S/C7H7BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5,10-11H

InChIKey

HJBGZJMKTOMQRR-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(C=O)=C1)(O)O

CAS DataBase Reference

87199-16-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

22-26-36/37/39-45-37/39-27

RIDADR 

UN 3261 8/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, MOISTURE SENSITIVE

PackingGroup 

Ⅲ

HS Code 

29319090

MSDS

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

3-Formylphenylboronic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

suzuki reaction

Uses

Reagent used:

• To study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye
• As exciton-coupled CD probes for epigallocatechin gallate

Biological inhibitor of γ-glutamyltranspeptidase

Reactant involved in:

• Palladium-catalyzed homocoupling
• Suzuki coupling reactions

Uses

3-Formylphenylboronic acid can be used as reagent to study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye and as exciton-coupled CD probes for epigallocatechin gallate Biological inhibitor of γ-glutamyltranspeptidase.

Synthesis

The general procedure for the synthesis of 3-formylphenylboronic acid from the compound (CAS:540777-53-5) and trimethyl borate was carried out as follows: firstly, a THF solution of trimethyl borate was prepared by adding 154.8 ml of trimethyl borate to a 3-liter three-necked flask, followed by 915 ml of tetrahydrofuran (THF). The solution was stirred under nitrogen protection and cooled with an ice bath. The cooled THF solution was slowly added to a 3-liter flask containing Grignard reagent through a stainless steel tube. The reaction mixture was stirred under ice bath cooling for 1 hour and then an aqueous sulfuric acid solution prepared from 30 ml of concentrated sulfuric acid and 480 ml of water was added. The temperature of the mixture was gradually brought to room temperature and stirring was continued at this temperature for 2 hours. After stopping stirring, the reaction mixture was allowed to stand at room temperature overnight. The precipitate was removed by filtration and the filtrate was concentrated. The concentrated residue was mixed with an equal volume of water and stirred at room temperature for 1 hour. The solid product was collected by filtration and dried to give 123.46 g of 3-formylphenylboronic acid in 88% yield. The 1H-NMR (200 MHz, CDCl3, δ ppm) data of the resulting product were as follows: 7.54 (t, J = 7.5 Hz, 1H), 7.93 (d, J = 6.1 Hz, 1H), 7.9-8.1 (br.d, 1H), 8.2-8.3 (br.s, 1H), 10.04 (s, 1H).

References

[1] BARTOSZ ZARYCHTA. 3-formylphenylboronic acid.[J]. Acta crystallographica. Section C, Crystal structure communications, 2004, 60 Pt 5: o344-5. DOI:10.1107/S0108270104006493.
[2] E. TANI?. Conformational, Structural, Vibrational, Electronic, and Molecular Docking Studies of 3-Formylphenylboronic Acid and 4-Formylphenylboronic Acid: A Comparative Study[J]. Russian Journal of Physical Chemistry A, 2020, 94 13: 2784-2796. DOI:10.1134/S0036024420130282.

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