Cas no 1086381-34-1 (2-bromo-4-(tert-butoxy)pyridine)

2-Bromo-4-(tert-butoxy)pyridine is a halogenated pyridine derivative featuring a tert-butoxy substituent at the 4-position and a bromine atom at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig aminations, owing to the reactivity of the bromine moiety. The tert-butoxy group enhances steric and electronic properties, making it useful for modifying reaction pathways or stabilizing intermediates. Its well-defined structure and functional group compatibility make it valuable for pharmaceutical and agrochemical applications, where precise molecular modifications are required. The compound is typically handled under inert conditions to preserve its stability.
2-bromo-4-(tert-butoxy)pyridine structure
1086381-34-1 structure
Product Name:2-bromo-4-(tert-butoxy)pyridine
CAS No:1086381-34-1
MF:C9H12BrNO
MW:230.10168170929
CID:2121879
PubChem ID:45787869
Update Time:2025-05-23

2-bromo-4-(tert-butoxy)pyridine Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-4-tert-butoxypyridine
    • 2-bromo-4-(tert-butoxy)pyridine
    • DA-15760
    • 2-bromo-4-[(2-methylpropan-2-yl)oxy]pyridine
    • DTXSID401281841
    • SCHEMBL14840716
    • 2-Bromo-4-(1,1-dimethylethoxy)pyridine
    • AKOS015942513
    • CS-0440917
    • 1086381-34-1
    • LTB38134
    • Inchi: 1S/C9H12BrNO/c1-9(2,3)12-7-4-5-11-8(10)6-7/h4-6H,1-3H3
    • InChI Key: RDPZXZISRGBKME-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=CN=1)OC(C)(C)C

Computed Properties

  • Exact Mass: 229.01023g/mol
  • Monoisotopic Mass: 229.01023g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 144
  • 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
  • XLogP3: 2.8
  • Topological Polar Surface Area: 22.1?2

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2-bromo-4-(tert-butoxy)pyridine Related Literature

Additional information on 2-bromo-4-(tert-butoxy)pyridine

2-Bromo-4-(tert-butoxy)Pyridine: A Comprehensive Overview

2-Bromo-4-(tert-butoxy)pyridine, also known by its CAS number 1086381-34-1, is a heterocyclic aromatic compound with significant applications in organic synthesis and materials science. This compound belongs to the pyridine family, a class of six-membered aromatic rings containing one nitrogen atom. The presence of a bromine atom at the 2-position and a tert-butoxy group at the 4-position imparts unique electronic and steric properties to the molecule, making it a valuable building block in various chemical reactions.

The synthesis of 2-bromo-4-(tert-butoxy)pyridine typically involves multi-step processes, often starting from pyridine derivatives. One common approach is the bromination of 4-(tert-butoxy)pyridine using brominating agents such as bromine (Br?) in the presence of a suitable catalyst or under specific reaction conditions. The tert-butoxy group is introduced via nucleophilic substitution or coupling reactions, depending on the starting material and desired regiochemistry. Recent advancements in catalytic methods have enabled more efficient and selective syntheses of this compound, reducing production costs and environmental impact.

In terms of physical properties, 2-bromo-4-(tert-butoxy)pyridine is a crystalline solid with a melting point around 150°C. Its solubility in organic solvents such as dichloromethane and THF is moderate, while it is poorly soluble in water due to its hydrophobic nature. The molecule exhibits strong UV absorption characteristics, which are attributed to its conjugated π-system. These properties make it suitable for applications in optoelectronic materials and sensors.

The electronic structure of 2-bromo-4-(tert-butoxy)pyridine has been extensively studied using computational chemistry methods. Density functional theory (DFT) calculations reveal that the bromine atom at the 2-position significantly affects the electron distribution within the ring, enhancing the electrophilic reactivity at certain positions. The tert-butoxy group, being an electron-donating substituent, stabilizes the molecule through resonance effects and provides steric bulk, which can influence reaction selectivity in subsequent transformations.

2-Bromo-4-(tert-butoxy)pyridine finds applications in various fields, including pharmaceuticals, agrochemicals, and advanced materials. In drug discovery, this compound serves as a key intermediate in the synthesis of bioactive molecules targeting cancer, inflammation, and infectious diseases. Recent studies have highlighted its potential as a lead compound for developing kinase inhibitors due to its ability to bind to specific protein domains.

In materials science, 2-bromo-4-(tert-butoxy)pyridine has been employed as a precursor for constructing coordination polymers and metal-organic frameworks (MOFs). Its bromine atom facilitates metal coordination, while the tert-butoxy group contributes to thermal stability and mechanical robustness of the resulting materials. Researchers have demonstrated that MOFs derived from this compound exhibit high surface areas and excellent gas adsorption capabilities, making them promising candidates for catalysis and energy storage applications.

The environmental impact of 2-bromo-4-(tert-butoxy)pyridine has also been a topic of interest. Studies on its biodegradation pathways indicate that under aerobic conditions, the compound undergoes microbial transformation through hydrolysis and oxidation mechanisms. However, further research is needed to assess its long-term persistence in natural ecosystems and potential risks to aquatic life.

In conclusion, 2-bromo-4-(tert-butoxy)pyridine (CAS No: 1086381-34-1) is a versatile compound with diverse applications across multiple disciplines. Its unique chemical properties, combined with recent advancements in synthesis and application techniques, position it as an important tool in modern chemistry research. Continued exploration into its reactivity, stability, and functionality will undoubtedly unlock new opportunities for innovation in both academic and industrial settings.

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