4-Hydroxyphenylboronic acid
Synonym(s):(p-Hydroxyphenyl)boronic acid;p-hydroxy-benzeneboronic acid;4-Hydroxybenzeneboronic acid;4-Hydroxyphenylboronic acid
- CAS NO.：71597-85-8
- Empirical Formula: C6H7BO3
- Molecular Weight: 137.93
- MDL number: MFCD01074628
- EINECS: 615-307-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-08 16:27:35
What is 4-Hydroxyphenylboronic acid?
Chemical properties
off-white to light brown powder
The Uses of 4-Hydroxyphenylboronic acid
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.
It can also be used to prepare/promote:
- 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.
The Uses of 4-Hydroxyphenylboronic acid
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.
Synthesis Reference(s)
Tetrahedron Letters, 37, p. 6705, 1996 DOI: 10.1016/S0040-4039(96)01468-2
Properties of 4-Hydroxyphenylboronic acid
| 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 |
| CAS DataBase Reference | 71597-85-8(CAS DataBase Reference) |
Safety information for 4-Hydroxyphenylboronic acid
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
| Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 4-Hydroxyphenylboronic acid
| InChIKey | COIQUVGFTILYGA-UHFFFAOYSA-N |
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