Cas no 849062-27-7 (3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid)

3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid is a versatile boronic acid derivative used primarily in Suzuki-Miyaura cross-coupling reactions, a key method for forming carbon-carbon bonds in organic synthesis. The presence of two bromine substituents enhances its reactivity and selectivity, making it valuable for constructing complex biaryl structures. Its boronic acid group facilitates efficient coupling with aryl halides under mild conditions, while the bromobenzyloxy moiety offers additional functionalization opportunities. This compound is particularly useful in pharmaceutical and materials science research, where precise molecular assembly is critical. Its stability under standard handling conditions and compatibility with diverse reaction environments further contribute to its utility in advanced synthetic applications.
3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid structure
849062-27-7 structure
Product Name:3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid
CAS No:849062-27-7
MF:C13H11BBr2O3
MW:385.843642473221
MDL:MFCD06411319
CID:716697
PubChem ID:24883037
Update Time:2025-06-13

3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • (3-Bromo-2-((3-bromobenzyl)oxy)phenyl)boronic acid
    • 3-BROMO-2-(3'-BROMOBENZYLOXY)PHENYLBORONIC ACID
    • 3-Bromo-2-(3-bromobenzyloxy)phenylboronic acid
    • Boronic acid,B-[3-bromo-2-[(3-bromophenyl)methoxy]phenyl]-
    • [3-bromo-2-[(3-bromophenyl)methoxy]phenyl]boronic acid
    • 3-BROMO-2-(3'-BROMOBENZYLOXY)PHENYLBORO&
    • Boronic acid, B-[3-bromo-2-[(3-bromophenyl)methoxy]phenyl]-
    • (3-Bromo-2-((3-bromobenzyl)oxy)phenyl)boronicacid
    • 849062-27-7
    • {3-Bromo-2-[(3-bromophenyl)methoxy]phenyl}boronic acid
    • MFCD06411319
    • AKOS015888511
    • SCHEMBL9893995
    • DTXSID40584551
    • BS-22497
    • 3-Bromo-2-(3''-bromobenzyloxy)phenylboronic Acid
    • C13H11BBr2O3
    • AB25227
    • 3-BROMO-2-[(3-BROMOPHENYL)METHOXY]PHENYLBORONIC ACID
    • CS-0175212
    • 3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid
    • MDL: MFCD06411319
    • Inchi: 1S/C13H11BBr2O3/c15-10-4-1-3-9(7-10)8-19-13-11(14(17)18)5-2-6-12(13)16/h1-7,17-18H,8H2
    • InChI Key: JWOHGYXQGYSJMX-UHFFFAOYSA-N
    • SMILES: B(C1=CC=CC(Br)=C1OCC1=CC=CC(Br)=C1)(O)O

Computed Properties

  • Exact Mass: 383.91700
  • Monoisotopic Mass: 383.91680g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 4
  • Complexity: 281
  • 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

  • Density: 1.79
  • Melting Point: 107-112?°C (lit.)
  • Boiling Point: 520.5°C at 760 mmHg
  • Flash Point: 268.6°C
  • Refractive Index: 1.662
  • PSA: 49.69000
  • LogP: 2.47040
  • Vapor Pressure: 0.0±1.4 mmHg at 25°C
  • pka: 7.56±0.53(Predicted)

3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid Security Information

  • Signal Word:warning
  • Hazard Statement: H413
  • Warning Statement: P264+P280+P305+P351+P338+P337+P313
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Safety Instruction: H303+H313+H333
  • Storage Condition:storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)

3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid Customs Data

  • HS CODE:2931900090
  • Customs Data:

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

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Additional information on 3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid

Comprehensive Overview of 3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid (CAS No. 849062-27-7)

3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid (CAS No. 849062-27-7) is a specialized boronic acid derivative widely utilized in organic synthesis, pharmaceutical research, and material science. This compound features a unique molecular structure combining bromine substituents and a boronic acid functional group, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions. Its dual reactivity enables the formation of complex biaryl structures, a critical step in developing drug candidates and advanced materials.

The growing demand for boronic acid-based compounds in medicinal chemistry has spotlighted 3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid as a key building block. Researchers frequently search for "boronic acid applications in drug discovery" or "Suzuki coupling reagents 2024," reflecting its relevance in cutting-edge science. This compound’s stability and compatibility with diverse reaction conditions align with trends favoring sustainable chemistry and high-yield synthetic routes.

From a structural perspective, the bromine atoms at the 3-position of the phenyl ring and the benzyloxy group enhance electrophilic reactivity, facilitating selective modifications. The boronic acid moiety (–B(OH)2) further allows for palladium-catalyzed transformations, a feature highly sought after in API manufacturing. Recent studies emphasize its role in synthesizing fluorescent probes and polymeric materials, addressing queries like "how to optimize boronic acid reactions" or "new boron-containing polymers."

In the context of green chemistry, 3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid exemplifies efficiency, as its byproducts are often non-toxic and recyclable. This aligns with industry shifts toward eco-friendly synthesis, a topic dominating forums such as "green alternatives for cross-coupling." Its compatibility with microwave-assisted synthesis also caters to labs prioritizing time-efficient protocols.

Handling and storage recommendations for this compound emphasize inert atmospheres and moisture-free conditions to preserve its reactivity. While not classified as hazardous, proper laboratory safety practices remain essential, echoing searches for "best practices for handling boronic acids." Its shelf stability and commercial availability (e.g., under catalog numbers like 849062-27-7) make it accessible for both academic and industrial projects.

In summary, 3-Bromo-2-(3'-bromobenzyloxy)phenylboronic acid bridges gaps between traditional organic synthesis and modern materials engineering. Its adaptability to high-throughput screening and catalysis research ensures continued relevance, answering trending questions like "what’s next in boron chemistry." As innovation accelerates, this compound will undoubtedly remain a cornerstone in molecular design.

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