Cas no 1062555-59-2 (4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane)

4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane is a high-purity boronic ester derivative commonly employed in Suzuki-Miyaura cross-coupling reactions. Its rigid naphthyl-phenyl backbone enhances stability, while the dioxaborolane moiety ensures efficient transmetalation under mild conditions. The steric hindrance from tetramethyl substitution improves selectivity in polyfunctional substrates, making it valuable for constructing complex biaryl systems. This compound exhibits excellent shelf stability and solubility in common organic solvents, facilitating handling in synthetic applications. Its consistent performance in palladium-catalyzed couplings makes it a reliable reagent for pharmaceutical and materials science research, particularly in the synthesis of conjugated polymers and heterocyclic frameworks.
4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane structure
1062555-59-2 structure
Product Name:4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane
CAS No:1062555-59-2
MF:C22H23BO2
MW:330.227826356888
MDL:MFCD22421637
CID:1025518
PubChem ID:58321129
Update Time:2025-11-02

4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane Chemical and Physical Properties

Names and Identifiers

    • 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane
    • 4,4,5,5-Tetramethyl-2-(2-(phthalen-2-yl)phenyl)-1,3,2-dioxaborolane
    • 4,4,5,5-tetramethyl-2-(2-naphthalen-2-ylphenyl)-1,3,2-dioxaborolane
    • 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)
    • 4,4,5,5-Tetramethyl-2-[2-(naphthalen-2-yl)phenyl]-1,3,2-dioxaborolane
    • C22H23BO2
    • AX8226135
    • AB0034620
    • ST24023024
    • X8799
    • (2-(NAPHTHALEN-2-YL)PHENYL)BORONIC ACID PINACOL ESTER
    • DB-305168
    • MFCD22421637
    • DS-1901
    • SCHEMBL12560678
    • 2-(2-Naphthyl)phenylboronic acid pinacol ester
    • 1062555-59-2
    • DTXSID90729096
    • CS-0175670
    • AKOS015998996
    • A895834
    • MDL: MFCD22421637
    • Inchi: 1S/C22H23BO2/c1-21(2)22(3,4)25-23(24-21)20-12-8-7-11-19(20)18-14-13-16-9-5-6-10-17(16)15-18/h5-15H,1-4H3
    • InChI Key: LIBLLUMMNMOCMY-UHFFFAOYSA-N
    • SMILES: O1B(C2=CC=CC=C2C2C=CC3C=CC=CC=3C=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 330.17900
  • Monoisotopic Mass: 330.1791101g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 2
  • Complexity: 459
  • 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

  • PSA: 18.46000
  • LogP: 4.80600

4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane Security Information

4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane Pricemore >>

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Additional information on 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane

Comprehensive Guide to 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (CAS No. 1062555-59-2)

4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (CAS No. 1062555-59-2) is a highly specialized boronic ester compound widely used in organic synthesis, pharmaceuticals, and materials science. This compound belongs to the dioxaborolane family, known for their stability and versatility in Suzuki-Miyaura cross-coupling reactions, a key method for forming carbon-carbon bonds in modern chemistry.

The molecular structure of 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane features a naphthalene moiety linked to a phenyl group, which is further connected to a dioxaborolane ring. This unique arrangement enhances its reactivity and makes it a valuable intermediate in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.

One of the most significant applications of 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane is in the field of drug discovery. Researchers frequently utilize this compound as a building block for the development of novel therapeutic agents. Its ability to participate in palladium-catalyzed coupling reactions allows for the efficient construction of biaryl structures, which are common in many FDA-approved drugs.

In addition to pharmaceutical applications, 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane is also employed in the production of organic electronic materials. Its conjugated aromatic system makes it suitable for use in OLEDs (Organic Light-Emitting Diodes) and photovoltaic devices, where it contributes to improved charge transport properties. This aligns with the growing demand for sustainable energy solutions and green chemistry practices.

The compound's stability under various conditions is another notable feature. Unlike some boronic acids, 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane is less prone to protodeboronation, making it a preferred choice for long-term storage and handling. This characteristic is particularly important for industrial-scale applications where consistency and reliability are paramount.

Recent advancements in catalysis and synthetic methodology have further expanded the utility of 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane. For instance, its use in flow chemistry setups has enabled more efficient and scalable production processes, addressing the need for cost-effective and environmentally friendly manufacturing techniques.

From a market perspective, the demand for 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane is expected to grow steadily, driven by its applications in high-value industries such as pharmaceuticals and electronics. Companies specializing in fine chemicals and custom synthesis are increasingly offering this compound to meet the needs of research and development laboratories worldwide.

For researchers and chemists working with 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane, it is essential to follow standard safety protocols. While the compound is not classified as hazardous, proper handling, including the use of personal protective equipment (PPE) and adequate ventilation, is recommended to ensure safe laboratory practices.

In summary, 4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (CAS No. 1062555-59-2) is a versatile and valuable compound with broad applications in organic synthesis, drug development, and material science. Its unique structural features and reactivity profile make it an indispensable tool for chemists and researchers aiming to push the boundaries of innovation in their respective fields.

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