Cas no 1227489-63-5 (3-Bromo-4-(trifluoromethyl)pyridin-2-amine)

3-Bromo-4-(trifluoromethyl)pyridin-2-amine is a halogenated pyridine derivative featuring both bromine and trifluoromethyl functional groups, which enhance its reactivity and utility in synthetic chemistry. The presence of the electron-withdrawing trifluoromethyl group and the bromine substituent makes it a valuable intermediate for cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the synthesis of complex heterocyclic compounds. Its amine functionality further allows for derivatization, expanding its applications in pharmaceutical and agrochemical research. The compound’s structural features contribute to its stability and selectivity in nucleophilic substitution reactions, making it a versatile building block for advanced chemical synthesis.
3-Bromo-4-(trifluoromethyl)pyridin-2-amine structure
1227489-63-5 structure
Product Name:3-Bromo-4-(trifluoromethyl)pyridin-2-amine
CAS No:1227489-63-5
MF:C6H4BrF3N2
MW:241.008570671082
CID:2619064
PubChem ID:98040679
Update Time:2025-05-21

3-Bromo-4-(trifluoromethyl)pyridin-2-amine Chemical and Physical Properties

Names and Identifiers

    • MFCD16606112
    • W16508
    • 1227489-63-5
    • KYUIKQXADNCVHA-UHFFFAOYSA-N
    • 3-Bromo-4-(trifluoromethyl)pyridin-2-amine
    • SY261369
    • 2-amino-3-bromo-4-(trifluoromethyl)pyridine
    • Inchi: 1S/C6H4BrF3N2/c7-4-3(6(8,9)10)1-2-12-5(4)11/h1-2H,(H2,11,12)
    • InChI Key: KYUIKQXADNCVHA-UHFFFAOYSA-N
    • SMILES: BrC1C(N)=NC=CC=1C(F)(F)F

Computed Properties

  • Exact Mass: 239.951
  • Monoisotopic Mass: 239.951
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 161
  • 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: 38.9A^2
  • XLogP3: 2.1

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Additional information on 3-Bromo-4-(trifluoromethyl)pyridin-2-amine

3-Bromo-4-(trifluoromethyl)pyridin-2-amine: A Comprehensive Overview

The compound with CAS No. 1227489-63-5, commonly referred to as 3-Bromo-4-(trifluoromethyl)pyridin-2-amine, is a fascinating molecule that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound is a derivative of pyridine, a six-membered aromatic heterocycle, and features a bromine atom at the 3-position and a trifluoromethyl group at the 4-position. The presence of these substituents imparts unique electronic and steric properties to the molecule, making it a valuable building block for various applications.

Pyridine derivatives have long been recognized for their versatility in chemical synthesis. The 3-bromo substitution in this compound introduces a reactive bromine atom, which can undergo nucleophilic substitution reactions under appropriate conditions. This makes it an ideal precursor for the synthesis of other pyridine derivatives with diverse functional groups. The trifluoromethyl group at the 4-position, on the other hand, contributes to the molecule's stability and enhances its lipophilicity, which is particularly advantageous in drug design.

Recent studies have highlighted the potential of 3-Bromo-4-(trifluoromethyl)pyridin-2-amine in medicinal chemistry. Researchers have explored its role as a lead compound for developing novel therapeutics targeting various diseases. For instance, its ability to modulate kinase activity has been investigated in preclinical models, showing promising results in inhibiting enzymes associated with cancer progression. The compound's unique structure allows for further functionalization, enabling the creation of more potent and selective drug candidates.

In addition to its pharmaceutical applications, 3-Bromo-4-(trifluoromethyl)pyridin-2-amine has found utility in materials science. Its aromaticity and electron-withdrawing groups make it a suitable candidate for designing advanced materials such as organic semiconductors and sensors. Recent advancements in nanotechnology have leveraged this compound's electronic properties to develop high-performance devices with applications in electronics and energy storage.

The synthesis of 3-Bromo-4-(trifluoromethyl)pyridin-2-amine typically involves multi-step reactions that require precise control over reaction conditions. Common methods include nucleophilic aromatic substitution and coupling reactions, often utilizing palladium catalysts to achieve high yields and selectivity. The development of efficient synthetic routes has been a focal point of recent research, driven by the increasing demand for this compound in both academic and industrial settings.

From an analytical standpoint, this compound can be characterized using a variety of techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and X-ray crystallography. These methods provide critical insights into its molecular structure, purity, and crystallinity, ensuring its suitability for downstream applications.

In conclusion, 3-Bromo-4-(trifluoromethyl)pyridin-2-amine is a versatile compound with a wide range of applications across multiple disciplines. Its unique chemical properties, combined with recent advancements in synthesis and application development, position it as an important tool in modern chemistry. As research continues to uncover new possibilities for this molecule, its role in advancing science and technology is expected to grow significantly.

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