Cas no 849052-17-1 (3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid)

3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid is a boronic acid derivative with significant utility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The presence of both bromo and boronic acid functional groups enables selective cross-coupling, facilitating the construction of complex biaryl structures. The 2'-chlorobenzyloxy substituent enhances steric and electronic modulation, improving reactivity in challenging coupling conditions. This compound is particularly valuable in pharmaceutical and agrochemical research, where precise functionalization of aromatic systems is required. Its stability under typical reaction conditions and compatibility with diverse catalysts make it a reliable intermediate for advanced synthetic applications. Proper handling under inert conditions is recommended to preserve its reactivity.
3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid structure
849052-17-1 structure
Product Name:3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid
CAS No:849052-17-1
MF:C14H13BBrClO3
MW:355.419222593308
MDL:MFCD06411364
CID:716655
PubChem ID:24882689
Update Time:2025-10-29

3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • (3-Bromo-2-((2-chlorobenzyl)oxy)-5-methylphenyl)boronic acid
    • 3-BROMO-2-(2'-CHLOROBENZYLOXY)-5-METHYLPHENYLBORONIC ACID
    • 3-Bromo-2-(2-chlorobenzyloxy)-5-methylphenylboronic acid
    • Boronic acid,B-[3-bromo-2-[(2-chlorophenyl)methoxy]-5-methylphenyl]-
    • [3-bromo-2-[(2-chlorophenyl)methoxy]-5-methylphenyl]boronic acid
    • Boronic acid, B-[3-bromo-2-[(2-chlorophenyl)methoxy]-5-methylphenyl]-
    • (3-Bromo-2-((2-chlorobenzyl)oxy)-5-methylphenyl)boronicacid
    • 849052-17-1
    • DTXSID80584499
    • 3-BROMO-2-[(2-CHLOROPHENYL)METHOXY]-5-METHYLPHENYLBORONIC ACID
    • MFCD06411364
    • 3-BROMO-2-(2'-CHLOROBENZYLOXY)-5-METHYL&
    • BS-17638
    • CS-0153365
    • 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid(contains varying amounts of Anhydride)
    • ZIB05217
    • AKOS015888504
    • D82442
    • 871126-00-0
    • {3-Bromo-2-[(2-chlorophenyl)methoxy]-5-methylphenyl}boronic acid
    • AB25277
    • SCHEMBL9893400
    • 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid
    • MDL: MFCD06411364
    • Inchi: 1S/C14H13BBrClO3/c1-9-6-11(15(18)19)14(12(16)7-9)20-8-10-4-2-3-5-13(10)17/h2-7,18-19H,8H2,1H3
    • InChI Key: VJOGFKWLTLTDCH-UHFFFAOYSA-N
    • SMILES: B(C1=CC(C)=CC(Br)=C1OCC1=CC=CC=C1Cl)(O)O

Computed Properties

  • Exact Mass: 353.98300
  • Monoisotopic Mass: 353.98296g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 4
  • Complexity: 308
  • 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: 49.7?2

Experimental Properties

  • Color/Form: No data available
  • Density: Not available
  • Melting Point: 123-128?°C (lit.)
  • Boiling Point: Not available
  • Flash Point: Not available
  • Refractive Index: 1.629
  • PSA: 49.69000
  • LogP: 2.66970
  • Vapor Pressure: Not available
  • pka: 7?+-.0.53(Predicted)

3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335-H413
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: S26; S36
  • Hazardous Material Identification: Xi
  • Risk Phrases:R36/37/38
  • Storage Condition:storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)

3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid Customs Data

  • HS CODE:2931900090

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3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid Related Literature

Additional information on 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic acid

3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid: A Comprehensive Overview

The compound 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid (CAS No. 849052-17-1) is a highly specialized organic compound with significant applications in the field of organic synthesis and materials science. This compound is characterized by its unique structure, which combines a bromine atom, a chlorobenzyl group, and a methyl group attached to a phenyl ring, with a boronic acid functionality. The presence of these functional groups makes it an invaluable building block in the construction of complex molecules, particularly in the realm of medicinal chemistry and advanced materials.

Recent advancements in synthetic methodologies have further highlighted the versatility of 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid. Researchers have employed this compound as a key intermediate in the synthesis of biologically active molecules, leveraging its reactivity under various coupling reactions. For instance, its boronic acid group enables efficient Suzuki-Miyaura coupling reactions, which are widely used to construct biaryl structures with high precision. This capability has been instrumental in the development of novel drug candidates targeting various therapeutic areas, including cancer and neurodegenerative diseases.

The structural complexity of 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid also makes it an attractive candidate for exploring new synthetic pathways. Recent studies have focused on optimizing its synthesis to enhance yield and purity while minimizing environmental impact. For example, green chemistry approaches, such as using microwave-assisted synthesis or catalytic systems, have been successfully applied to streamline the production process. These innovations not only improve the efficiency of chemical manufacturing but also align with global sustainability goals.

In addition to its role in drug discovery, 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid has found applications in materials science. Its ability to participate in cross-coupling reactions has been exploited in the synthesis of advanced polymers and nanomaterials. For instance, researchers have utilized this compound to create stimuli-responsive polymers that exhibit dynamic properties under external stimuli, such as temperature or pH changes. These materials hold promise for applications in sensors, drug delivery systems, and adaptive coatings.

The growing interest in 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid is also driven by its potential in chemical biology. Its unique structure allows for the exploration of novel bioconjugation strategies, enabling the creation of probes for studying cellular processes at the molecular level. Recent advancements in click chemistry and bioorthogonal reactions have further expanded its utility in this domain.

From an analytical standpoint, the characterization of 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid has benefited from modern spectroscopic techniques. High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy have provided detailed insights into its molecular structure and purity. These analytical tools are essential for ensuring the quality and consistency of this compound during both research and industrial-scale production.

In conclusion, 3-Bromo-2-(2'-chlorobenzyloxy)-5-methylphenylboronic Acid (CAS No. 849052-17-1) stands as a testament to the ingenuity of modern organic chemistry. Its versatile structure and reactivity continue to drive innovation across multiple disciplines, from drug discovery to materials science. As research progresses, this compound is expected to unlock new possibilities for creating advanced materials and therapeutic agents that address pressing challenges in healthcare and technology.

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