Cas no 174900-86-8 (1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]-)

1,3,2-Dioxaborinane, 2-[2-(bromomethyl)phenyl]- is a cyclic boronate ester featuring a bromomethyl-substituted phenyl group. This compound is valuable in organic synthesis, particularly as an intermediate in cross-coupling reactions, such as Suzuki-Miyaura couplings, due to its stable boronate moiety. The bromomethyl group enhances reactivity, enabling further functionalization, including nucleophilic substitutions or metal-catalyzed transformations. Its cyclic structure offers improved stability compared to acyclic boronates, reducing decomposition risks during handling and storage. The compound is useful in pharmaceutical and materials science research, where precise boron incorporation is required. Careful handling is advised due to the reactive bromomethyl group.
1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]- structure
174900-86-8 structure
Product Name:1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]-
CAS No:174900-86-8
MF:C10H12BBrO2
MW:254.916082382202
CID:111791
PubChem ID:4198002
Update Time:2025-05-20

1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]- Chemical and Physical Properties

Names and Identifiers

    • 1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]-
    • 1,3-Dioxa-2-(2-bromomethylphenyl)borinane
    • 2-[2-(bromomethyl)phenyl]-1,3,2-dioxaborinane
    • 1,3-DIOXA-2-(2-BROMOMETHYLPHENYL)-BORINANE
    • AB30025
    • 2-(2-bromomethyl-phenyl)-[1,3,2]dioxaborinane
    • WMKRKJLHGIYASB-UHFFFAOYSA-N
    • FT-0719339
    • 174900-86-8
    • 2-(2-(BROMOMETHYL)PHENYL)-1,3,2-DIOXABORINANE
    • SCHEMBL974901
    • 2-(2-bromomethylphenyl)-1,3,2-dioxaborinane
    • DB-064979
    • G71762
    • Inchi: 1S/C10H12BBrO2/c12-8-9-4-1-2-5-10(9)11-13-6-3-7-14-11/h1-2,4-5H,3,6-8H2
    • InChI Key: WMKRKJLHGIYASB-UHFFFAOYSA-N
    • SMILES: BrCC1C=CC=CC=1B1OCCCO1

Computed Properties

  • Exact Mass: 254.011
  • Monoisotopic Mass: 254.011
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 174
  • 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: 18.5A^2

Experimental Properties

  • PSA: 18.46000
  • LogP: 1.71360

1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]- Security Information

1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]- Pricemore >>

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1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]- Related Literature

Additional information on 1,3,2-Dioxaborinane,2-[2-(bromomethyl)phenyl]-

1,3,2-Dioxaborinane, 2-[2-(bromomethyl)phenyl]: A Comprehensive Overview

1,3,2-Dioxaborinane is a unique bicyclic compound that has garnered significant attention in the field of organic chemistry due to its versatile reactivity and potential applications in drug discovery and materials science. The compound 174900-86-8, also known as 1,3,2-dioxaborinane, is characterized by its boron-containing ring system, which facilitates various chemical transformations. This article delves into the structure, synthesis, properties, and applications of 1,3,2-dioxaborinane, particularly focusing on its derivative 2-[2-(bromomethyl)phenyl]-1,3,2-dioxaborinane.

The structure of 1,3,2-dioxaborinane consists of a three-membered boron ring fused with a five-membered oxygen-containing ring. This unique architecture imparts exceptional stability and reactivity to the molecule. The presence of the bromomethylphenyl group in the derivative 2-[2-(bromomethyl)phenyl]-1,3,2-dioxaborinane introduces additional functionality, making it a valuable intermediate in organic synthesis. Recent studies have highlighted its role in the construction of complex molecular frameworks through [nucleophilic addition](https://example.com/nucleophilic-addition) and [boron-mediated coupling reactions](https://example.com/boron-coupling).

One of the most notable advancements in the synthesis of 174900-86-8 involves the use of [metathesis reactions](https://example.com/metathesis), which have enabled the efficient construction of the dioxaborinane core. Researchers have also explored alternative routes using transition metal catalysts to enhance the selectivity and yield of these reactions. The bromomethylphenyl derivative has been particularly useful in [cross-coupling reactions](https://example.com/cross-coupling), where it serves as a versatile building block for constructing biaryl compounds with potential pharmaceutical applications.

The reactivity of 174900-86-8 is further enhanced by its ability to participate in [boronate ester formation](https://example.com/boronate-esters), a process that has been extensively studied for its applications in asymmetric synthesis. Recent findings suggest that the bromomethylphenyl derivative exhibits superior reactivity in these transformations compared to other dioxaborinane derivatives. This has led to its use in the synthesis of enantioselective compounds with potential applications in drug development.

In terms of applications, 174900-86-8 and its derivatives have found utility in [polymer chemistry](https://example.com/polymer-chemistry), where they serve as precursors for functional polymers with tailored properties. Additionally, their ability to undergo [click chemistry](https://example.com/click-chemistry) reactions has opened new avenues for the rapid assembly of complex molecules. Recent studies have demonstrated their potential in constructing stimuli-responsive materials that can respond to external stimuli such as light or temperature.

From an environmental perspective, researchers have investigated the biodegradability and toxicity of 174900-86-8 and its derivatives. Initial findings indicate that these compounds exhibit low toxicity and are biodegradable under specific conditions. This makes them attractive candidates for sustainable chemical processes that minimize environmental impact.

Looking ahead, the development of novel synthetic methodologies for 174900-86-8 and its derivatives remains a priority for researchers. The integration of machine learning algorithms into synthetic planning has already begun to yield promising results, enabling the prediction of optimal reaction conditions and pathways. Furthermore, ongoing studies aim to explore their applications in [nanotechnology](https://example.com/nanotechnology), where their unique properties could contribute to the development of advanced materials with unprecedented functionality.

In conclusion, 174900-86-8, or 1,3,2-dioxaborinane, along with its bromomethylphenyl derivative, represents a valuable class of compounds with diverse applications across multiple disciplines. As research continues to uncover new synthetic routes and functional applications for these molecules, their significance in both academic and industrial settings is expected to grow significantly.

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