Structure

4-Iodophenylboronic acid

CAS
5122-99-6
Catalog Number
ACM5122996
Category
Boronic Acids
Molecular Weight
247.83g/mol
Molecular Formula
C6H6BIO2

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Specification

Synonyms
4-IODOBENZENEBORONIC ACID;4-IODOPHENYLBORONIC ACID;RARECHEM AH PB 0035;P-IODOPHENYLBORONIC ACID;4-Iodophenylboronic acid,97%;p-IodophenylboromcAcid;4-Iodophenylboronic acid ,98%;4-Iodophenylboronic
IUPAC Name
(4-iodophenyl)boronic acid
Canonical SMILES
B(C1=CC=C(C=C1)I)(O)O
InChI
InChI=1S/C6H6BIO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
InChI Key
PELJYVULHLKXFF-UHFFFAOYSA-N
Application
4-Iodophenylboronic acid is a versatile white crystalline powder that serves as a key reagent in a variety of advanced chemical reactions. It plays a crucial role in copper-mediated ligandless aerobic fluoroalkylation and palladium-catalyzed aerobic oxidative cross-coupling reactions. Its utility extends to the realm of recyclable magnetic-nanoparticle-supported palladium catalysis in Suzuki coupling reactions, offering efficient oxidative hydroxylation with copper catalysts. Moreover, it is involved in ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling and homocoupling processes using gold salts as catalysts. Additionally, 4-Iodophenylboronic acid is employed in ruthenium-catalyzed cross-coupling and CuI-catalyzed Suzuki coupling reactions. It supports complex transformations such as palladium-catalyzed domino Heck-Mizoroki/Suzuki-Miyaura reactions and facilitates manganese triacetate-mediated radical additions of arylboronic acids to alkenes. Beyond these applications, this reagent is integral to the preparation of pleuromutilin derivatives, aimed at ribosomal binding and antibacterial activity via "Click Chemistry," as well as in the development of liquid crystalline polyacetylene derivatives.
Complexity
102
Covalently-Bonded Unit Count
1
Exact Mass
247.95056g/mol
Formal Charge
0
H-Bond Acceptor
2
H-Bond Donor
2
Heavy Atom Count
10
Monoisotopic Mass
247.95056g/mol
Rotatable Bond Count
1
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