Cas no 851178-96-6 (4-bromo-2,3,5-trifluoro-pyridine)

4-Bromo-2,3,5-trifluoropyridine is a halogenated pyridine derivative with significant utility in pharmaceutical and agrochemical synthesis. Its key structural features—a bromo substituent at the 4-position and trifluorination at the 2, 3, and 5-positions—enhance reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, while the electron-withdrawing fluorine atoms improve stability and influence regioselectivity. This compound serves as a versatile intermediate for constructing complex heterocyclic frameworks. Its high purity and well-defined reactivity profile make it suitable for precision applications in medicinal chemistry and material science. Proper handling under inert conditions is recommended due to its sensitivity to moisture and potential lability under strong nucleophilic conditions.
4-bromo-2,3,5-trifluoro-pyridine structure
851178-96-6 structure
Product Name:4-bromo-2,3,5-trifluoro-pyridine
CAS No:851178-96-6
MF:C5HBrF3N
MW:211.967350721359
MDL:MFCD08436092
CID:990027
PubChem ID:26986296
Update Time:2025-06-22

4-bromo-2,3,5-trifluoro-pyridine Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-2,3,5-trifluoropyridine
    • PC9693
    • QC-6964
    • 4-bromo-2,3,5-trifluoro-pyridine
    • MFCD08436092
    • 851178-96-6
    • FT-0706384
    • DTXSID70650531
    • AKOS022187453
    • CS-0437011
    • DB-082026
    • MDL: MFCD08436092
    • Inchi: 1S/C5HBrF3N/c6-3-2(7)1-10-5(9)4(3)8/h1H
    • InChI Key: FSEIUJXQVPRMHU-UHFFFAOYSA-N
    • SMILES: BrC1C(=CN=C(C=1F)F)F

Computed Properties

  • Exact Mass: 210.92400
  • Monoisotopic Mass: 210.924
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 124
  • 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: 12.9A^2
  • XLogP3: 2.2

Experimental Properties

  • Density: 1.901
  • Boiling Point: 158.2°C at 760 mmHg
  • Flash Point: 49.5°C
  • Refractive Index: 1.486
  • PSA: 12.89000
  • LogP: 2.26140

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Additional information on 4-bromo-2,3,5-trifluoro-pyridine

4-Bromo-2,3,5-Trifluoro-Pyridine (CAS No. 851178-96-6): An Overview of Its Synthesis, Applications, and Recent Research

4-Bromo-2,3,5-trifluoro-pyridine (CAS No. 851178-96-6) is a versatile and important compound in the field of organic chemistry and pharmaceutical research. This compound is characterized by its unique bromo and trifluoro substituents on the pyridine ring, which confer it with a range of valuable properties. In this article, we will delve into the synthesis methods, applications, and recent research developments surrounding 4-bromo-2,3,5-trifluoro-pyridine.

Synthesis of 4-Bromo-2,3,5-Trifluoro-Pyridine

The synthesis of 4-bromo-2,3,5-trifluoro-pyridine has been a topic of significant interest due to its utility as an intermediate in the preparation of various pharmaceuticals and agrochemicals. One of the most common methods involves the bromination of 2,3,5-trifluoropyridine. This process typically starts with the preparation of 2,3,5-trifluoropyridine through a series of reactions involving fluorination and cyclization steps. The bromination can be achieved using bromine or a brominating agent such as N-bromosuccinimide (NBS) in an appropriate solvent.

Recent advancements in synthetic methodologies have focused on improving the efficiency and selectivity of these reactions. For instance, a study published in the Journal of Organic Chemistry reported a novel method using transition-metal catalysis to achieve high yields and excellent regioselectivity in the bromination step. This approach not only enhances the overall yield but also reduces the formation of by-products, making it more suitable for large-scale production.

Applications of 4-Bromo-2,3,5-Trifluoro-Pyridine

4-Bromo-2,3,5-trifluoro-pyridine finds extensive use as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure makes it an ideal building block for constructing complex molecules with specific biological activities. One notable application is in the development of antiviral agents. The presence of bromo and trifluoro substituents allows for fine-tuning of the pharmacological properties of the final drug molecules.

In addition to its role in pharmaceuticals, 4-bromo-2,3,5-trifluoro-pyridine is also utilized in the synthesis of agrochemicals. Its ability to form stable complexes with metal ions makes it useful in designing pesticides and herbicides with enhanced efficacy and reduced environmental impact.

Recent Research Developments

The ongoing research on 4-bromo-2,3,5-trifluoro-pyridine has led to several significant findings that have broadened its applications and improved its synthetic routes. A recent study published in Angewandte Chemie explored the use of this compound as a precursor for novel fluorinated materials with potential applications in electronics and materials science. The researchers demonstrated that by modifying the substitution pattern on the pyridine ring, they could achieve materials with tailored electronic properties.

In another study published in Chemical Communications, scientists investigated the use of 4-bromo-2,3,5-trifluoro-pyridine in the development of new catalysts for asymmetric synthesis. The unique electronic properties of this compound allowed for the design of highly efficient catalysts that could selectively produce enantiomerically pure products. This breakthrough has significant implications for the pharmaceutical industry, where enantiomeric purity is crucial for drug efficacy and safety.

Safety Considerations

Safety is a paramount concern when handling any chemical compound. While 4-bromo-2,3,5-trifluoro-pyridine is not classified as a hazardous material under current regulations, it is important to follow standard laboratory safety protocols when working with this compound. Proper personal protective equipment (PPE), such as gloves and goggles, should be worn at all times. Additionally, fume hoods should be used to minimize exposure to vapors.

In conclusion, 4-bromo-2,3,5-trifluoro-pyridine (CAS No. 851178-96-6) is a valuable compound with diverse applications in organic chemistry and pharmaceutical research. Its unique structure and properties make it an essential building block for synthesizing complex molecules with specific biological activities. Ongoing research continues to expand its potential uses and improve its synthetic methods.

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