Cas no 957111-27-2 ((S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid)

(S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid is a chiral binaphthyl-based boronic acid derivative, widely utilized in asymmetric synthesis and catalysis. Its rigid, axially chiral structure makes it an effective ligand for transition-metal catalysts, particularly in enantioselective transformations such as C–C bond formations and Suzuki-Miyaura couplings. The presence of boronic acid groups enhances its utility in cross-coupling reactions, while the hydroxyl groups facilitate coordination with metals, improving catalytic efficiency. This compound is valued for its high stereochemical stability and versatility in constructing complex chiral frameworks, making it a preferred choice in pharmaceutical and fine chemical synthesis. Its well-defined chirality ensures consistent enantioselectivity in asymmetric reactions.
(S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid structure
957111-27-2 structure
Product Name:(S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid
CAS No:957111-27-2
MF:C20H16B2O6
MW:373.959445953369
MDL:MFCD09258753
CID:857724
Update Time:2025-05-26

(S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid Chemical and Physical Properties

Names and Identifiers

    • (S)-2,2-Dihydroxy-1,1-binaphthalene-3,3-diboronic acid
    • [4-(3-borono-2-hydroxynaphthalen-1-yl)-3-hydroxynaphthalen-2-yl]boronic acid
    • (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid
    • B-5133
    • I04-7011
    • MDL: MFCD09258753
    • Inchi: 1S/C20H16B2O6/c23-19-15(21(25)26)9-11-5-1-3-7-13(11)17(19)18-14-8-4-2-6-12(14)10-16(20(18)24)22(27)28/h1-10,23-28H
    • InChI Key: JQGYHOADNLSJJI-UHFFFAOYSA-N
    • SMILES: OC1C(B(O)O)=CC2C=CC=CC=2C=1C1=C(C(B(O)O)=CC2C=CC=CC1=2)O

Computed Properties

  • Exact Mass: 374.11300

Experimental Properties

  • PSA: 121.38000
  • LogP: 0.43080

(S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid Customs Data

  • HS CODE:2918290000
  • Customs Data:

    China Customs Code:

    2918290000

    Overview:

    2918290000 Other carboxylic acids and anhydrides containing phenolic groups but not other oxy groups\Acyl halide\Peroxides and peroxyacids and their derivatives.Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods).VAT:17.0%.Tax refund rate:9.0%.MFN tariff:6.5%.general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Regulatory conditions:

    A.Customs clearance form for Inbound Goods
    B.Customs clearance form for outbound goods

    Inspection and quarantine category:

    R.Sanitary supervision and inspection of imported food
    S.Sanitary supervision and inspection of exported food

    Summary:

    HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

(S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid Pricemore >>

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D678928-50mg
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abcr
AB271013-500 mg
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abcr
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Additional information on (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid

Recent Advances in the Application of (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid (CAS: 957111-27-2) in Chemical Biology and Pharmaceutical Research

The compound (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid (CAS: 957111-27-2) has emerged as a pivotal molecule in chemical biology and pharmaceutical research due to its unique structural and functional properties. Recent studies have highlighted its potential as a versatile building block for asymmetric synthesis, chiral recognition, and targeted drug delivery systems. This research brief synthesizes the latest findings on this compound, focusing on its applications in medicinal chemistry and biotechnology.

One of the most significant advancements involves the use of (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid as a chiral ligand in catalytic asymmetric reactions. Researchers have demonstrated its efficacy in facilitating enantioselective transformations, such as the Suzuki-Miyaura cross-coupling reaction, which is critical for the synthesis of complex bioactive molecules. The boronic acid functional groups in this compound enable precise control over stereochemistry, making it invaluable for the production of enantiomerically pure pharmaceuticals.

In addition to its role in catalysis, this compound has shown promise in the development of biosensors and diagnostic tools. Its ability to form stable complexes with diols and other biologically relevant molecules has been exploited for glucose sensing and other biomarker detection applications. Recent studies have optimized the binding affinity and selectivity of (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid, paving the way for its integration into next-generation diagnostic platforms.

Another groundbreaking application is in targeted drug delivery systems. The boronic acid moieties of this compound can interact with cell surface glycans, enabling the selective delivery of therapeutic agents to specific tissues or cell types. Preclinical studies have demonstrated its potential in enhancing the efficacy of anticancer drugs while minimizing off-target effects. Researchers are now exploring its use in combination therapies and personalized medicine approaches.

Despite these promising developments, challenges remain in the large-scale synthesis and stability of (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid. Recent efforts have focused on improving synthetic routes and derivatization strategies to enhance its practicality for industrial applications. Advances in green chemistry and continuous flow synthesis are expected to address these limitations in the near future.

In conclusion, (S)-2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-diboronic acid (CAS: 957111-27-2) represents a multifaceted tool in chemical biology and pharmaceutical research. Its applications span from asymmetric catalysis to biosensing and targeted drug delivery, underscoring its versatility and potential for transformative impact. Continued research and development efforts are essential to fully unlock its capabilities and translate these findings into clinical and industrial applications.

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