Cas no 1080632-76-3 (2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a high-purity boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. Its extended terphenyl backbone enhances steric stability, improving selectivity in polyaryl synthesis. The tetramethyl dioxaborolane group offers excellent air and moisture stability, facilitating handling and storage compared to more labile boronic acids. This compound is particularly valuable in constructing complex conjugated systems for organic electronics, pharmaceuticals, and advanced materials. Its consistent reactivity and compatibility with diverse reaction conditions make it a reliable intermediate for precision aryl-aryl bond formation. Suitable for both academic research and industrial applications, it ensures high yields with minimal side products.
2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane structure
1080632-76-3 structure
Product Name:2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS No:1080632-76-3
MF:C24H25BO2
MW:356.265106916428
MDL:MFCD16294429
CID:2194411
PubChem ID:58160927
Update Time:2025-06-12

2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical and Physical Properties

Names and Identifiers

    • 4,4,5,5-Tetramethyl-2-[1,1’:4’,1’’-terphenyl]-4-yl-1,3,2-dioxaborolane
    • 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 4,4,5,5-Tetramethyl-2-[1,1':4',1''-terphenyl]-4-yl-1,3,2-dioxaborolane
    • 4-terphenyl boronic acid pinacol ester
    • p-Terphenyl, 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
    • 4,4,5,5-tetramethyl-2-[4-(4-phenylphenyl)phenyl]-1,3,2-dioxaborolane
    • [1,1':4',1''-terphenyl]-4-boronic acid pinacol ester
    • DS-15393
    • 2-(4-{[1,1'-BIPHENYL]-4-YL}PHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
    • MFCD16294429
    • 1080632-76-3
    • CS-0161995
    • C71297
    • AKOS022179318
    • [1,1':4',1''-Terphenyl]-4-boronicacidpinacolester
    • T3875
    • SCHEMBL10021061
    • MDL: MFCD16294429
    • Inchi: 1S/C24H25BO2/c1-23(2)24(3,4)27-25(26-23)22-16-14-21(15-17-22)20-12-10-19(11-13-20)18-8-6-5-7-9-18/h5-17H,1-4H3
    • InChI Key: POKQNZPMVVRGTB-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC(C3C=CC(C4C=CC=CC=4)=CC=3)=CC=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 356.1947602g/mol
  • Monoisotopic Mass: 356.1947602g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 3
  • Complexity: 465
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 18.5

Experimental Properties

  • Density: 1.10

2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Pricemore >>

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Additional information on 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Introduction to 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 1080632-76-3)

2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, also known by its CAS number 1080632-76-3, is a versatile organic compound that has garnered significant attention in the fields of organic synthesis and medicinal chemistry. This compound belongs to the class of boronic esters and is characterized by its unique structural features and reactivity. Its applications range from synthetic intermediates to ligands in catalytic reactions and precursors in pharmaceutical development.

The molecular structure of 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is particularly noteworthy due to the presence of a terphenyl moiety and a dioxaborolane ring. The terphenyl group imparts rigidity and planarity to the molecule, which can be advantageous in various chemical reactions. The dioxaborolane ring, on the other hand, is a stable boronic ester derivative that can participate in Suzuki-Miyaura coupling reactions, making this compound a valuable reagent in organic synthesis.

In recent years, the use of boronic esters like 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been extensively explored in the development of new materials and pharmaceuticals. One of the key applications of this compound is in the synthesis of complex organic molecules and natural products. The Suzuki-Miyaura coupling reaction is a palladium-catalyzed cross-coupling reaction that efficiently forms carbon-carbon bonds between aryl or vinyl boronic acids or esters and aryl or vinyl halides. This reaction has become a cornerstone in modern synthetic chemistry due to its high efficiency and functional group tolerance.

Beyond its use as a synthetic intermediate, 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has shown promise in medicinal chemistry. The terphenyl moiety can serve as a scaffold for designing molecules with specific biological activities. For instance, terphenyl derivatives have been investigated for their potential as anticancer agents due to their ability to interact with specific protein targets. The dioxaborolane ring can also be used to introduce boron atoms into molecules for boron neutron capture therapy (BNCT), a promising approach for treating certain types of cancer.

The stability and reactivity of 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane make it an attractive candidate for various catalytic processes. In particular, it can serve as a ligand in palladium-catalyzed reactions where its unique electronic properties can influence the selectivity and efficiency of the catalytic cycle. Recent studies have demonstrated that boronic esters with bulky substituents like terphenyl groups can enhance the performance of catalysts by stabilizing transition states and intermediates.

In addition to its synthetic and catalytic applications, 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been studied for its potential use in materials science. The rigid structure of the terphenyl moiety can be utilized to create ordered molecular assemblies with specific optical and electronic properties. These assemblies have potential applications in organic electronics and photovoltaic devices.

The preparation of 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane typically involves multi-step synthetic routes that start from readily available starting materials. One common approach is to first synthesize the terphenyl derivative and then introduce the dioxaborolane ring through a suitable boronation reaction. The choice of reagents and conditions can significantly affect the yield and purity of the final product.

To ensure high-quality synthesis and characterization of 2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, advanced analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) are often employed. These techniques provide detailed information about the molecular structure and purity of the compound. Additionally,crystallographic studies using X-ray diffraction can offer insights into the solid-state properties of this compound,which are crucial for understanding its behavior in various applications.

In conclusion,2-([[[[[[[[[[[[[[[[[[[[[[[[[[[[[''']--Terphenyl]-An>-yL])-An>,An>,An>,An>,An>-tetraMeTHyL-An>,An>-dIoXoBoRoLaNe (CAS No. 08063-An>-7-An>-3)) is a multifunctional compound with significant potential in various fields of chemistry and materials science. Its unique structural features make it an excellent candidate for synthetic intermediates,catalytic ligands,and precursors in pharmaceutical development. Ongoing research continues to uncover new applications for this compound,highlighting its importance in modern scientific endeavors.>">>">>">>">>">>">>">>">>">>">>">>">>">>">"""""""""""""

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