Description

Diphenylborinic Anhydride (CAS No. 4426-21-5) is a highly specialized organoboron compound with the molecular formula C₂₄H₂₀B₂O. This anhydride derivative of diphenylborinic acid is widely utilized in advanced organic synthesis, catalysis, and materials science research. Its IUPAC name, diphenylboranyloxy(diphenyl)borane, reflects its structural configuration, featuring two phenyl groups bonded to each boron center with a bridging oxygen atom.

This compound is supplied as a high-purity crystalline solid, ensuring consistency for sensitive applications. It is particularly valued for its role as a Lewis acid catalyst in cross-coupling reactions and as a precursor for boron-containing polymers. Researchers appreciate its stability under inert conditions and compatibility with a range of organic solvents including THF, toluene, and dichloromethane.

Our Diphenylborinic Anhydride undergoes rigorous quality control, with batch-specific certificates of analysis available upon request. Suitable for use in glove box environments, this reagent is packaged under inert gas to maintain purity. Synonyms include 1,1,3,3-Tetraphenyldiboroxane and diphenylboronic anhydride.

Properties

• CAS Number: 4426-21-5
• Complexity: 331
• IUPAC Name: diphenylboranyloxy(diphenyl)borane
• InChI: InChI=1S/C24H20B2O/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)27-26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
• InChI Key: SNQFEECGHGUHBK-UHFFFAOYSA-N
• Exact Mass: 346.1700256
• Molecular Formula: C24H20B2O
• Molecular Weight: 346.0
• SMILES: B(C1=CC=CC=C1)(C2=CC=CC=C2)OB(C3=CC=CC=C3)C4=CC=CC=C4
• Topological: 9.2
• Monoisotopic Mass: 346.1700256
• Synonyms: Diphenylborinic anhydride, 4426-21-5, 1,1,3,3-Tetraphenyldiboroxane, diphenylboranyloxy(diphenyl)borane, diphenylboronic anhydride, Tetraphenyldiboroxane, MFCD00042663, diphenylboranyl diphenylborinate, Diphenylborinic anhydride, 95%, CHEMBL2386188, Oxybis(diphenylborane), Borane, oxybis[diphenyl-, diphenyl borinic anhydride, SCHEMBL435243, GTPL2494, DTXSID90344425, 1,1,3,3-Tetraphenyldiboroxane #, BDBM50434534, di(phenyl)boranyloxy-di(phenyl)borane, AKOS015892763, CS-W011885, AS-58629, SY224274, DB-170831, D77726, Q27077074, Diphenylborinic anhydride, purum p.a., for fluorescence, >=95.0% (T), InChI=1/C24H20B2O/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)27-26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20

Application

Diphenylborinic Anhydride serves as a versatile reagent in Suzuki-Miyaura cross-coupling reactions, facilitating carbon-carbon bond formation in complex organic syntheses. It acts as an effective Lewis acid catalyst in Diels-Alder and aldol condensation reactions. Researchers employ this compound in the development of boron-doped organic electronic materials due to its electron-deficient properties. Additionally, it finds use as a stabilizing agent for transition metal catalysts in polymerization processes.

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