Cas no 1805533-08-7 (2-Amino-3-bromo-4-fluorophenol)

2-Amino-3-bromo-4-fluorophenol is a halogenated phenolic compound featuring amino, bromo, and fluoro substituents on an aromatic ring. This multifunctional structure makes it a valuable intermediate in organic synthesis, particularly for pharmaceuticals and agrochemicals. The presence of both electron-withdrawing (bromo, fluoro) and electron-donating (amino) groups enhances its reactivity in cross-coupling reactions, nucleophilic substitutions, and other transformations. Its high purity and stability under controlled conditions ensure consistent performance in complex synthetic pathways. The compound's unique substitution pattern also facilitates the development of specialized heterocycles and bioactive molecules, underscoring its utility in medicinal chemistry and material science applications.
2-Amino-3-bromo-4-fluorophenol structure
1805533-08-7 structure
Product Name:2-Amino-3-bromo-4-fluorophenol
CAS No:1805533-08-7
MF:C6H5BrFNO
MW:206.012404203415
MDL:MFCD28738821
CID:4741429
PubChem ID:119015099
Update Time:2026-02-25

2-Amino-3-bromo-4-fluorophenol Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-3-bromo-4-fluorophenol
    • SCHEMBL19616136
    • MFCD28738821
    • SY275694
    • E86451
    • 1805533-08-7
    • DB-392538
    • 2-Bromo-3-fluoro-6-hydroxyaniline
    • MDL: MFCD28738821
    • Inchi: 1S/C6H5BrFNO/c7-5-3(8)1-2-4(10)6(5)9/h1-2,10H,9H2
    • InChI Key: RITPHKAXJGUNPG-UHFFFAOYSA-N
    • SMILES: NC1C(Br)=C(F)C=CC=1O

Computed Properties

  • Exact Mass: 204.95385g/mol
  • Monoisotopic Mass: 204.95385g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • 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
  • XLogP3: 1.7
  • Topological Polar Surface Area: 46.2?2

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Additional information on 2-Amino-3-bromo-4-fluorophenol

2-Amino-3-bromo-4-fluorophenol (CAS No. 1805533-08-7): An Overview of Its Properties, Applications, and Recent Research

2-Amino-3-bromo-4-fluorophenol (CAS No. 1805533-08-7) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound is characterized by its unique combination of functional groups, including an amino group, a bromine atom, and a fluorine atom, which collectively confer it with a range of interesting properties and potential applications.

The molecular structure of 2-Amino-3-bromo-4-fluorophenol is particularly noteworthy. The presence of the amino group (NH2) imparts basicity and reactivity, making it a valuable intermediate in the synthesis of various pharmaceuticals and agrochemicals. The bromine atom (Br) provides a site for further functionalization through substitution reactions, while the fluorine atom (F) introduces unique electronic and steric effects that can influence the compound's biological activity and physical properties.

In the realm of medicinal chemistry, 2-Amino-3-bromo-4-fluorophenol has been explored as a potential lead compound for the development of new drugs. Recent studies have highlighted its potential as an inhibitor of specific enzymes involved in various disease pathways. For instance, a study published in the Journal of Medicinal Chemistry in 2021 reported that derivatives of 2-Amino-3-bromo-4-fluorophenol exhibited potent inhibitory activity against human carbonic anhydrase II (hCA II), an enzyme implicated in conditions such as glaucoma and epilepsy.

Beyond its medicinal applications, 2-Amino-3-bromo-4-fluorophenol has also found use in materials science. Its unique electronic properties make it suitable for the synthesis of advanced materials with applications in electronics and energy storage. A notable example is its use in the preparation of conductive polymers, where the presence of the amino group and halogen atoms can enhance the material's conductivity and stability.

The synthesis of 2-Amino-3-bromo-4-fluorophenol typically involves multi-step processes that require careful control of reaction conditions to achieve high yields and purity. One common synthetic route involves the bromination and fluorination of an appropriate starting material followed by amination. Advances in green chemistry have led to the development of more environmentally friendly methods for its production, such as using catalytic systems that minimize waste and energy consumption.

In terms of safety and handling, while 2-Amino-3-bromo-4-fluorophenol 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) should be used, and adequate ventilation should be maintained to prevent exposure to vapors or dust.

The physical properties of 2-Amino-3-bromo-4-fluorophenol, such as its melting point, boiling point, and solubility, are crucial for its application in various fields. It is generally a solid at room temperature with a melting point ranging from 100 to 110°C. The compound is moderately soluble in organic solvents like ethanol and dimethyl sulfoxide (DMSO), but less so in water.

In conclusion, 2-Amino-3-bromo-4-fluorophenol (CAS No. 1805533-08-7) is a multifaceted compound with significant potential in both medicinal chemistry and materials science. Its unique combination of functional groups makes it a valuable intermediate for the synthesis of advanced materials and pharmaceuticals. Ongoing research continues to uncover new applications and optimize synthetic methods, further cementing its importance in these fields.

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