4-Acetylphenylboronic acid Chemical Properties

Melting point:

240-244 °C(lit.)

Boiling point:

354.2±44.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

7.58±0.10(Predicted)

color 

Pale yellow to yellow

Water Solubility 

25 g/L

BRN 

7869162

CAS DataBase Reference

149104-90-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29310095

MSDS

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

4-Acetylphenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

suzuki reaction

Uses

Reactant involved in:

• Palladium-catalyzed decarboxylative coupling
• Copper-catalyzed hydroxylation
• Palladium-catalyzed Suzuki-Miyaura cross-coupling
• Cross-coupling with α-bromocarbonyl compounds
• Oxidation catalyzed by Baeyer-Villiger monooxygenases
• 1,5-substitution reactions

Uses

4-Acetylphenylboronic acid4-Acetylphenylboronic Acid is used in several metal catalyzed cross-coupling reaction studies.

General Description

4-Acetylphenylboronic acid is a boronate, belongs to a class of synthetic organic compounds. It reacts rapidly with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives. It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II), during the synthesis of dendrimers.

Synthesis

The general procedure for the synthesis of (R)-1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-ol and 4-acetylphenylboronic acid from 1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-ol was carried out in the following manner: under aseptic conditions, the appropriate racemic alcohol ( 0.5 mmol) was dissolved in dimethylformamide (2 mL) and added to a 500 mL conical flask containing 8.2 g of wet cells (resuspended in 100 mL of phosphate buffer, pH 7.0, 100 mmol/L). The reaction was carried out at 20°C and 400 rpm for 120 hours. After completion of the reaction, the reaction mixture was extracted for 24 h using a continuous liquid-liquid extractor and dichloromethane (300 mL). The organic layer was dried with anhydrous magnesium sulfate followed by evaporation of the solvent under reduced pressure. The crude product was purified by column chromatography using hexane/ethyl acetate as eluent.

References

[1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 110, p. 117 - 125

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