4-Hydroxyphenylboronic acid

• CAS: 71597-85-8
• Catalog Number: ACM71597858
• Category: Boronic Acids
• Molecular Weight: 137.93
• Molecular Formula: C6H7BO3
• Synonyms: p-Hydroxy-benzeneboronic acid
• IUPAC Name: (4-hydroxyphenyl)boronic acid
• Canonical SMILES: B(C1=CC=C(C=C1)O)(O)O
• InChI: InChI=1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
• InChI Key: COIQUVGFTILYGA-UHFFFAOYSA-N
• Boiling Point: 351.4 °C
• Melting Point: 230 °C
• Density: 1.32 g/ml
• Application: 4-Hydroxyphenylboronic acid serves as a versatile reactant with a variety of applications in organic synthesis and pharmaceuticals. It is prominently used in Suzuki-Miyaura and Stille coupling reactions, as well as in palladium-catalyzed aminocarbonylation and cross-coupling procedures, including the Suzuki reaction aimed at creating bio-supported palladium nanoparticles, which act as phosphine-free catalysts. Additionally, it facilitates Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles. Beyond these applications, 4-Hydroxyphenylboronic acid contributes to the development of bioactive compounds, such as promoting PDK1 inhibitory activity, which is crucial in inhibiting cancer cell growth and tumor progression. It is instrumental in the synthesis of rod-like dendronized polymers through the macromonomer approach by living ROMP, as well as in crafting estrone-derived cyclopamine analogs, which function as Sonic Hedgehog signaling inhibitors for anti-cancer therapeutics. Furthermore, it aids the preparation of enzymatic inhibitors targeting Gram-negative bacterial infections and the formation of oligoarenes through Suzuki-Miyaura palladium-catalyzed cross-coupling, underscoring its broad utility in scientific research and medicinal chemistry.
• Complexity: 99.2
• Covalently-Bonded Unit Count: 1
• Exact Mass: 138.048824g/mol
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Heavy Atom Count: 10
• Monoisotopic Mass: 138.048824g/mol
• Rotatable Bond Count: 1

Custom Q&A

What is the molecular formula of 4-Hydroxyphenylboronic acid?

The molecular formula of 4-Hydroxyphenylboronic acid is C6H7BO3.

What is the molecular weight of 4-Hydroxyphenylboronic acid?

The molecular weight of 4-Hydroxyphenylboronic acid is 137.93 g/mol.

What is the IUPAC name of 4-Hydroxyphenylboronic acid?

The IUPAC name of 4-Hydroxyphenylboronic acid is (4-hydroxyphenyl)boronic acid.

What is the InChI of 4-Hydroxyphenylboronic acid?

The InChI of 4-Hydroxyphenylboronic acid is InChI=1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H.

What is the InChIKey of 4-Hydroxyphenylboronic acid?

The InChIKey of 4-Hydroxyphenylboronic acid is COIQUVGFTILYGA-UHFFFAOYSA-N.

What is the canonical SMILES of 4-Hydroxyphenylboronic acid?

The canonical SMILES of 4-Hydroxyphenylboronic acid is B(C1=CC=C(C=C1)O)(O)O.

What is the CAS number of 4-Hydroxyphenylboronic acid?

The CAS number of 4-Hydroxyphenylboronic acid is 71597-85-8.

What is the ChEMBL ID of 4-Hydroxyphenylboronic acid?

The ChEMBL ID of 4-Hydroxyphenylboronic acid is CHEMBL3218996.

What is the DSSTox Substance ID of 4-Hydroxyphenylboronic acid?

The DSSTox Substance ID of 4-Hydroxyphenylboronic acid is DTXSID00370250.

Is 4-Hydroxyphenylboronic acid a canonicalized compound?

Yes, 4-Hydroxyphenylboronic acid is a canonicalized compound according to PubChem.