Cas no 849052-24-0 (3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid)

3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, a key methodology in synthetic organic chemistry. Its structure features both a boronic acid group, enabling efficient palladium-catalyzed couplings, and a bromo substituent, offering additional reactivity for further functionalization. The 3-methoxybenzyloxy moiety enhances solubility and stability, facilitating handling and storage. This compound is particularly valuable in pharmaceutical and materials science research for constructing complex biaryl and heteroaryl systems. Its high purity and well-defined reactivity make it a reliable intermediate for synthesizing advanced organic frameworks.
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid structure
849052-24-0 structure
Product Name:3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
CAS No:849052-24-0
MF:C14H14BBrO4
MW:336.973563671112
MDL:MFCD06411374
CID:716662
PubChem ID:24883405
Update Time:2025-08-05

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

Names and Identifiers

    • (3-Bromo-2-((3-methoxybenzyl)oxy)phenyl)boronic acid
    • 3-BROMO-2-(3'-METHOXYBENZYLOXY)PHENYLBORONIC ACID
    • 3-Bromo-2-(3-methoxybenzyloxy)phenylboronic acid
    • Boronic acid,B-[3-bromo-2-[(3-methoxyphenyl)methoxy]phenyl]-
    • MFCD06411374
    • [3-bromo-2-[(3-methoxyphenyl)methoxy]phenyl]boronic acid
    • {3-Bromo-2-[(3-methoxyphenyl)methoxy]phenyl}boronic acid
    • 849052-24-0
    • 3-BROMO-2-[(3-METHOXYPHENYL)METHOXY]PHENYLBORONIC ACID
    • 3-Bromo-2-(3''-methoxybenzyloxy)phenylboronic Acid
    • SCHEMBL9905525
    • 3-BROMO-2-(3'-METHOXYBENZYLOXY)PHENYLBO&
    • BS-23050
    • CS-0174334
    • C14H14BBrO4
    • AB25296
    • (3-Bromo-2-((3-methoxybenzyl)oxy)phenyl)boronicacid
    • ZIB05224
    • DTXSID70584589
    • AKOS015888891
    • G68004
    • 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
    • MDL: MFCD06411374
    • Inchi: 1S/C14H14BBrO4/c1-19-11-5-2-4-10(8-11)9-20-14-12(15(17)18)6-3-7-13(14)16/h2-8,17-18H,9H2,1H3
    • InChI Key: JNPYQBOHAURAQI-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC(B(O)O)=C1OCC1C=CC=C(C=1)OC

Computed Properties

  • Exact Mass: 336.01700
  • Monoisotopic Mass: 336.01685g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 5
  • Complexity: 292
  • 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: 58.9?2

Experimental Properties

  • Density: 1.5
  • Melting Point: 86-91?°C (lit.)
  • Boiling Point: 503.9°C at 760 mmHg
  • Flash Point: 258.6°C
  • Refractive Index: 1.615
  • PSA: 58.92000
  • LogP: 1.71650

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

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • 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

3-Bromo-2-(3'-methoxybenzyloxy)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%

3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
abcr
AB271670-250 mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid; 95%
849052-24-0
250mg
€140.60 2023-04-26
Alichem
A019115891-5g
(3-Bromo-2-((3-methoxybenzyl)oxy)phenyl)boronic acid
849052-24-0 95%
5g
$400.00 2023-08-31
Chemenu
CM137220-1g
(3-Bromo-2-((3-methoxybenzyl)oxy)phenyl)boronic acid
849052-24-0 95%
1g
$228 2023-02-01
TRC
B694613-25mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
25mg
$ 64.00 2023-04-18
TRC
B694613-50mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
50mg
$ 69.00 2023-04-18
TRC
B694613-100mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
100mg
$ 92.00 2023-04-18
TRC
B694613-250mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
250mg
$ 161.00 2023-04-18
Apollo Scientific
OR360791-100mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
100mg
£87.00 2025-02-19
Apollo Scientific
OR360791-250mg
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
250mg
£151.00 2025-02-19
Apollo Scientific
OR360791-1g
3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid
849052-24-0
1g
£396.00 2025-02-19

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

Introduction to 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic Acid (CAS No. 849052-24-0)

3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid is a sophisticated organic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound, identified by its unique Chemical Abstracts Service (CAS) number 849052-24-0, is a boronic acid derivative with a brominated aromatic ring and a methoxybenzyl ether side chain. Its structural features make it a valuable intermediate in the synthesis of various bioactive molecules, particularly in the development of targeted therapeutics and advanced materials.

The utility of 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid stems from its ability to participate in diverse chemical transformations, including Suzuki-Miyaura cross-coupling reactions, which are pivotal in constructing complex molecular architectures. The presence of both a boronic acid moiety and a bromine substituent on the phenyl ring provides multiple handles for further functionalization, enabling chemists to tailor the compound for specific applications.

In recent years, boronic acids have emerged as critical components in drug discovery due to their role as key intermediates in the synthesis of protease inhibitors and other therapeutic agents. The bromine atom in this compound allows for further modifications via palladium-catalyzed reactions, making it an attractive building block for medicinal chemists. Additionally, the methoxybenzyl ether group enhances solubility and stability, which are essential properties for pharmaceutical intermediates.

One of the most compelling aspects of 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid is its potential application in the development of novel materials. Boronic acids are known for their ability to form reversible covalent bonds with diols, a property that has been exploited in self-healing polymers and smart materials. The bromine substituent further extends these possibilities by enabling additional cross-linking reactions, thereby expanding the range of material properties that can be engineered.

Recent research has highlighted the role of this compound in the synthesis of kinase inhibitors, which are widely used in cancer therapy. The structural motif present in 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid closely resembles scaffolds found in several FDA-approved drugs. By leveraging its reactivity, researchers have been able to develop new analogs with improved pharmacokinetic profiles and enhanced target specificity. This underscores the importance of boronic acid derivatives as versatile tools in modern drug design.

The synthesis of 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid involves multi-step organic transformations that require precise control over reaction conditions. The introduction of the boronic acid functionality typically involves halogenation followed by lithiation and subsequent quenching with an aldehyde or ketone derivative. The subsequent methoxybenzyl ether formation adds another layer of complexity but is crucial for achieving the desired molecular architecture.

In terms of industrial applications, 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid has found use in the production of advanced electronic materials. Boron-containing compounds are integral to semiconductor manufacturing due to their ability to form stable crystalline structures at high temperatures. The bromine atom facilitates further functionalization via metal-catalyzed reactions, allowing for the creation of complex thin films and coatings that exhibit unique electronic properties.

The pharmaceutical industry has also explored the use of this compound in the development of diagnostic agents. Boron neutron capture therapy (BNCT) is an emerging modality for treating cancer that relies on boron-containing compounds to selectively target malignant cells. The high affinity of boronic acids for certain biomolecules makes them ideal candidates for BNCT applications. While further research is needed to fully realize this potential, preliminary studies suggest that derivatives like 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid could play a significant role in next-generation cancer treatments.

Another area where this compound has shown promise is in the field of green chemistry. The ability to perform multiple functionalizations under mild conditions reduces waste and energy consumption, aligning with sustainable practices. Researchers have demonstrated that 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid can be synthesized using catalytic amounts of palladium without generating harmful byproducts. This approach not only improves efficiency but also minimizes environmental impact.

The future prospects for 3-Bromo-2-(3'-methoxybenzyloxy)phenylboronic acid are vast and multifaceted. As our understanding of molecular interactions deepens, so too does our ability to harness its potential for innovative applications. Whether it is through drug discovery, material science, or diagnostic imaging, this compound represents a cornerstone of modern chemical research. Its unique structural features continue to inspire new methodologies and applications, ensuring its relevance across multiple disciplines.

Recommended suppliers
Essenoi Fine Chemical Co., Limited
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Nantong Boya Environmental Protection Technology Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Nantong Boya Environmental Protection Technology Co., Ltd
Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Reagent
Amadis Chemical Company Limited
Tiancheng Chemical (Jiangsu) Co., Ltd
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Shandong Jing Kun Chemical Co.,Ltd.
Gold Member
Audited Supplier Audited Supplier
CN Supplier
Bulk
Shandong Jing Kun Chemical Co.,Ltd.