Cas no 517874-21-4 (2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a boronic ester derivative commonly used as an intermediate in Suzuki-Miyaura cross-coupling reactions. Its stable dioxaborolane structure ensures improved handling and storage compared to boronic acids, while the dihydrobenzodioxin moiety offers versatility in pharmaceutical and agrochemical synthesis. The tetramethyl substitution enhances steric protection, increasing stability under reactive conditions. This compound is particularly valuable in constructing complex heterocyclic frameworks due to its compatibility with diverse functional groups. Its high purity and consistent reactivity make it a reliable choice for precision organic synthesis, particularly in medicinal chemistry applications where controlled coupling is critical.
2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane structure
517874-21-4 structure
Product Name:2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS No:517874-21-4
MF:C14H19BO4
MW:262.109264612198
MDL:MFCD05663890
CID:366475
PubChem ID:2760592
Update Time:2025-06-30

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical and Physical Properties

Names and Identifiers

    • 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 1,4-BENZODIOXANE-6-BORONIC ACID, PINACOL ESTER
    • 1,4-Benzodioxin,2,3-dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
    • 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 1,4-Benzodioxane-6-boronic acid
    • 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzo-1,4-dioxoline
    • SCHEMBL14212260
    • Z1336745096
    • AS-2970
    • 517874-21-4
    • J-503965
    • 1,4-Benzodioxane-6-boronic acid pinacol ester
    • 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzo[1,4]dioxine
    • A828774
    • (2,3-DIHYDROBENZO[B][1,4]DIOXIN-6-YL)BORONIC ACID PINACOL ESTER
    • AKOS015951058
    • 1,4-Benzodioxane-6-boronic acid, pinacol ester, AldrichCPR
    • WIIBAHCYWOUFRM-UHFFFAOYSA-N
    • 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzo-1,4-dioxine, AldrichCPR
    • EN300-212568
    • MFCD05663890
    • 1,4-Benzodioxane-6-boronic acid, pinacol ester;
    • CS-0094700
    • AB22036
    • DTXSID60375246
    • 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzodioxine
    • 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,4-Benzodioxane-6-boronic acid, pinacol ester
    • 2-FLUORO-3-METHYLBENZYLALCOHOL
    • MDL: MFCD05663890
    • Inchi: 1S/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)10-5-6-11-12(9-10)17-8-7-16-11/h5-6,9H,7-8H2,1-4H3
    • InChI Key: WIIBAHCYWOUFRM-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC3=C(C=2)OCCO3)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 262.13800
  • Monoisotopic Mass: 262.138
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 1
  • Complexity: 328
  • 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: 36.9A^2

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.13
  • Melting Point: 54-55°C
  • Boiling Point: 360.2°C at 760 mmHg
  • Flash Point: 171.7°C
  • Refractive Index: 1.52
  • PSA: 36.92000
  • LogP: 1.75700
  • Vapor Pressure: No data available

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Security Information

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-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%

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Pricemore >>

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Additional information on 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 517874-21-4): An Overview

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 517874-21-4) is a versatile compound with significant applications in the fields of medicinal chemistry and materials science. This compound belongs to the class of boronic esters and is characterized by its unique structural features and chemical properties. The compound's structure includes a 2,3-dihydrobenzo[b][1,4]dioxin moiety and a 1,3,2-dioxaborolane ring system, which contribute to its reactivity and stability in various chemical reactions.

The CAS No. 517874-21-4 compound has gained considerable attention in recent years due to its potential in the synthesis of bioactive molecules and its use in Suzuki-Miyaura cross-coupling reactions. These reactions are widely employed in the synthesis of complex organic molecules, particularly in the development of pharmaceuticals and advanced materials. The presence of the boronic ester functionality makes this compound an excellent coupling partner for aryl and vinyl halides, enabling the formation of carbon-carbon bonds under mild conditions.

In the context of medicinal chemistry, 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been explored for its potential in drug discovery and development. Recent studies have highlighted its role in the synthesis of compounds with anti-inflammatory and anticancer properties. For instance, a study published in the Journal of Medicinal Chemistry reported the successful synthesis of a series of derivatives using this compound as a key intermediate. These derivatives exhibited potent inhibitory activity against specific cancer cell lines and showed promising results in preclinical trials.

The structural versatility of CAS No. 517874-21-4 also makes it an attractive candidate for the development of new materials with enhanced properties. Researchers have utilized this compound in the synthesis of polymers and coatings with improved thermal stability and mechanical strength. A notable example is a study published in Advanced Materials, where a novel polymer containing this boronic ester was synthesized and characterized. The resulting material demonstrated excellent thermal resistance and was proposed for use in high-performance applications such as aerospace and electronics.

Beyond its applications in pharmaceuticals and materials science, 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has also been investigated for its potential in catalysis. The boronic ester functionality can serve as a ligand for transition metal catalysts, enhancing their activity and selectivity in various catalytic processes. A recent study published in Catalysis Today explored the use of this compound as a ligand in palladium-catalyzed reactions. The results showed that the presence of this ligand significantly improved the yield and selectivity of the reactions compared to conventional ligands.

The synthesis of CAS No. 517874-21-4 typically involves multi-step procedures that require careful control of reaction conditions to ensure high yields and purity. Common synthetic routes include the formation of the boronic ester from a corresponding boronic acid or boronate ester followed by functional group transformations to introduce the desired substituents. Advances in synthetic methodologies have led to more efficient and scalable processes for producing this compound on both laboratory and industrial scales.

In conclusion, 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 517874-21-4) is a highly valuable compound with diverse applications across multiple scientific disciplines. Its unique chemical structure and reactivity make it an essential tool for researchers working on drug discovery, materials science, and catalysis. As ongoing research continues to uncover new possibilities for this compound, it is expected to play an increasingly important role in advancing these fields.

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