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Benzene-1,4-diboronic acid

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Catalog Number
ACM4612264-1
Product Name
Benzene-1,4-diboronic acid
Structure
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CAS
4612-26-4
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Synonyms
Benzene-1,4-diboronic acid, NSC 25410, p-Phenylenediboronic acid, 1,4-Phenylenediboronic acid, p-Benzenediboronic acid
Molecular Weight
165.75
Molecular Formula
C6H4[B(OH)2]2
Canonical SMILES
OB(O)c1ccc(cc1)B(O)O
InChI
1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H
InChI Key
BODYVHJTUHHINQ-UHFFFAOYSA-N
Melting Point
>350 °C (lit.)
Purity
≥95.0%
Appearance
White to Off White; Powder or Chunks
Application
Benzene-1,4-diboronic acid serves as a versatile reagent with several significant applications in both chemical synthesis and materials science. It is primarily utilized in Suzuki-Miyaura cross-coupling reactions, facilitating the formation of carbon-carbon bonds crucial for organic synthesis. Additionally, this compound is employed in palladium-catalyzed sequential alkenylation and conjugate addition reactions, as well as in Scholl cyclizations, which are essential for complex molecular constructions. Beyond its synthetic capabilities, benzene-1,4-diboronic acid plays a role in externally initiated Kumada catalyst-transfer polycondensation and energy transfer processes within optoelectronic devices, such as organic light-emitting diodes (OLEDs) and organic thin-film transistors. The compound also contributes to the development of fluorescence and solution-processable coordination polymers, highlighting its importance in advancing both chemical methodology and electronic material innovation.
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