(4-Hydroxy-2-methyl)phenylboronic acid Chemical Properties

Melting point:

100-104°C

Boiling point:

361.4±52.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

9.17±0.58(Predicted)

color 

White to Almost white

CAS DataBase Reference

493035-82-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41

Safety Statements 

26-36/37/39-39

HazardClass 

IRRITANT

HS Code 

2931900090

(4-Hydroxy-2-methyl)phenylboronic acid Usage And Synthesis

Uses

suzuki reaction

Uses

(4-Hydroxy-2-methylphenyl)boronic Acid is a reactant in the preparation of biarylmethoxy nicotinamides as specific inhibitors of mycobacterium tuberculosis

Synthesis

The general procedure for the synthesis of 4-hydroxy-2-methylphenylboronic acid from 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is as follows: 1. sodium periodate (2.39 g, 11.15 mmol) was added to acetone and water (2:1, 36 mL) containing 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (870.4 mg, 3.72 mmol) and ammonium acetate (859.8 mg, 11.15 mmol) in a room temperature in a mixed solution. 2. The reaction mixture was stirred for 68 hours, then filtered and concentrated. 3. 3. Sodium chloride was added to the concentrated filtrate and extracted with ethyl acetate. 4. 4. The organic layer was dried with anhydrous magnesium sulfate, followed by filtration and concentration. 5. 5. The residue was purified by silica gel chromatography using 1:4 ethyl acetate:hexane as eluent to afford 275.7 mg (49% yield) of 4-hydroxy-2-methylphenylboronic acid as a solid. Product characterization data: 1H NMR (400 MHz, d6-DMSO): δ 9.28 (s, 1H), 7.70 (d, J = 9 Hz, 1H), 6.56-6.52 (m, 2H), 2.55 (s, 3H). ESI-LCMS m/z 151 (M-H)-.

References

[1] Patent: US2008/96921, 2008, A1. Location in patent: Page/Page column 82

(4-Hydroxy-2-methyl)phenylboronic acid(493035-82-8)Related Product Information

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