71597-85-8 | 4-Hydroxyphenylboronic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$5.00	$4.00
5g	98%	in stock	$8.00	$6.00
10g	98%	in stock	$13.00	$10.00
25g	98%	in stock	$18.00	$12.00
50g	98%	in stock	$33.00	$23.00
100g	98%	in stock	$65.00	$45.00

Description

• Catalog Number: AB45040
• Chemical Name: 4-Hydroxyphenylboronic acid
• CAS Number: 71597-85-8
• Molecular Formula: C6H7BO3
• Molecular Weight: 137.929
• MDL Number: MFCD01074628
• SMILES: Oc1ccc(cc1)B(O)O

Computed Properties

• Complexity: 99.2
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 1

Upstream Synthesis Route

4-Hydroxyphenylboronic acid, also known as 4-HPBA, is a versatile organoboron compound widely used in chemical synthesis. Its primary application lies in its ability to form stable boronate esters with diols or polyols under mild conditions. This unique reactivity makes 4-HPBA a valuable tool in organic chemistry for various transformations and reactions.In chemical synthesis, 4-Hydroxyphenylboronic acid is commonly employed in Suzuki-Miyaura cross-coupling reactions to construct carbon-carbon bonds. By reacting with aryl halides or pseudohalides in the presence of a palladium catalyst, 4-HPBA facilitates the formation of biaryl compounds with high efficiency. This makes it an essential component in the synthesis of pharmaceuticals, agrochemicals, and functional materials.Furthermore, 4-HPBA can participate in directed ortho-metalation reactions, where it serves as a directing group to enable selective functionalization of aromatic rings. This strategy allows for the introduction of various substituents at specific positions on the phenyl ring, expanding the synthetic possibilities and structural diversity of organic molecules.Additionally, 4-Hydroxyphenylboronic acid exhibits potential in the development of sensors and materials for biomedical applications. Its ability to bind to diols or polyols with high affinity can be exploited for the detection of sugars or as a molecular recognition element in supramolecular chemistry.Overall, the unique reactivity and versatile applications of 4-Hydroxyphenylboronic acid make it a valuable building block in chemical synthesis, enabling the efficient construction of complex organic molecules and materials.

Literature

• Novel tricyclic pyrazole BRAF inhibitors with imidazole or furan central scaffolds.

  Bioorganic & medicinal chemistry 20100915

• Small molecules showing significant protection of mice against botulinum neurotoxin serotype A.

  PloS one 20100101