4-Hydroxyphenylboronic acid Chemical Properties

Melting point:

>230 °C (lit.)

Boiling point:

351.4±44.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Acetonitrile, DMSO, Methanol

form 

Powder

pka

9.09±0.10(Predicted)

color 

Off-white to light brown

Water Solubility 

25 g/L

BRN 

2963491

InChIKey

COIQUVGFTILYGA-UHFFFAOYSA-N

CAS DataBase Reference

71597-85-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34

Safety Statements 

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

WGK Germany 

3

TSCA 

No

HS Code 

2931 90 00

HazardClass 

IRRITANT

MSDS

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

4-Hydroxyphenylboronic acid Usage And Synthesis

Chemical Properties

off-white to light brown powder

Uses

4-Hydroxybenzeneboronic acid is used for Suzuki-Miyaura coupling and Stille coupling and potential for introducing different alkyl groups, palladium-catalyzed aminocarbonylation and cross-coupling reactions, bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water and Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles. It is also used in preparation of rod-like dendronized polymers.

Uses

4-Hydroxyphenylboronic acid can be used as a reactant in:

• Suzuki-Miyaura coupling and Stille coupling reactions.
• Palladium-catalyzed aminocarbonylation and cross-coupling reactions.
• Suzuki reaction for preparation of bio-supported palladium nanoparticles as phosphine-free catalysts.
• Cu₂O-catalyzed aerobic oxidative cross-coupling of tetrazoles.

• PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor).
• Rod-like dendronized polymers containing G4 and G5 ester dendrons via macromonomer approach by living ROMP.
• Estrone-derived cyclopamine analogs as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics.
• Enzymatic inhibitors for the treatment of Gram-negative bacterial infections.
• Oligoarenes by Suzuki-Miyaura palladium-catalyzed cross-coupling.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 6705, 1996 DOI: 10.1016/S0040-4039(96)01468-2

4-Hydroxyphenylboronic acid(71597-85-8)Related Product Information

• Triclosan
• Phenylboronic acid
• 4-Methoxyphenol
• 3-Hydroxybenzoic acid
• 4-Carboxyphenylboronic acid
• 4-Hydroxybenzaldehyde
• 2-Hydroxyphenylacetic acid
• 4-Hydroxybenzoic acid
• 4-Aminophenylboronic acid
• 4-Cyanophenol
• Methylparaben
• 3-Carboxyphenylboronic acid
• 1,4-Benzodioxane-6-boronic acid
• 4-Trifluoromethoxyphenylboronic acid
• 4-(N-OCTYLOXY)BENZENEBORONIC ACID
• 3-Hydroxyphenylboronic acid
• Carboxy styrene-butadiene latex
• 2,4-Dimethoxybenzeneboronic acid