Cas no 1227601-75-3 (2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine)

2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine is a halogenated pyridine derivative with a hydroxymethyl functional group at the 4-position, offering versatile reactivity for synthetic applications. The presence of both bromo and fluoro substituents enhances its utility as a building block in pharmaceutical and agrochemical synthesis, enabling selective cross-coupling and nucleophilic substitution reactions. The hydroxymethyl group provides an additional site for further functionalization, such as oxidation or esterification. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules due to its balanced reactivity and stability. Its well-defined structure ensures consistent performance in multi-step synthetic routes.
2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine structure
1227601-75-3 structure
Product Name:2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine
CAS No:1227601-75-3
MF:C6H5BrFNO
MW:206.012404203415
MDL:MFCD16606993
CID:1057764
PubChem ID:74892526
Update Time:2025-10-30

2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine Chemical and Physical Properties

Names and Identifiers

    • 2-BROMO-3-FLUORO-4-(HYDROXYMETHYL)PYRIDINE
    • (2-Bromo-3-fluoropyridin-4-yl)methanol
    • (2-Bromo-3-fluoro-4-pyridinyl)methanol
    • AK174173
    • 2-Bromo-3-fluoropyridine-4-methanol
    • FCH1343693
    • 4-Pyridinemethanol, 2-bromo-3-fluoro-
    • DS-8613
    • DB-200092
    • MFCD16606993
    • AKOS025396404
    • 1227601-75-3
    • SB55285
    • s10012
    • SCHEMBL20607540
    • SY026534
    • 2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine
    • MDL: MFCD16606993
    • Inchi: 1S/C6H5BrFNO/c7-6-5(8)4(3-10)1-2-9-6/h1-2,10H,3H2
    • InChI Key: PESRNDDYOHOPPV-UHFFFAOYSA-N
    • SMILES: BrC1C(=C(C=CN=1)CO)F

Computed Properties

  • Exact Mass: 204.95385g/mol
  • Monoisotopic Mass: 204.95385g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 114
  • 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: 33.1
  • XLogP3: 1.1

Experimental Properties

  • Boiling Point: 292.7±35.0°C at 760 mmHg

2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine Security Information

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Additional information on 2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine

Professional Introduction to 2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine (CAS No: 1227601-75-3)

2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. With the CAS number 1227601-75-3, this compound represents a critical intermediate in the synthesis of various biologically active molecules. Its unique structural features, including a bromo and fluoro substituent on a pyridine ring with a hydroxymethyl group, make it an attractive scaffold for drug discovery and development.

The< strong>pyridine core is a well-documented pharmacophore in medicinal chemistry, contributing to the biological activity of numerous therapeutic agents. The presence of both< strong>bromo and< strong>fluoro atoms introduces electrophilic and nucleophilic sites, respectively, which can be exploited for further functionalization. This dual reactivity makes< strong>2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine a valuable building block for constructing complex molecular architectures.

In recent years, there has been a surge in research focused on developing novel treatments for various diseases, including cancer, infectious diseases, and neurological disorders. The< strong>hydroxymethyl group in this compound provides a handle for further derivatization, enabling the creation of diverse analogs with tailored biological properties. For instance, hydroxymethyl groups can be oxidized to aldehydes or carboxylic acids, or reduced to alcohols, offering multiple pathways for structural diversification.

The< strong>bromo substituent on the pyridine ring is particularly useful for cross-coupling reactions such as Suzuki-Miyaura, Buchwald-Hartwig, and Negishi couplings. These reactions are fundamental in constructing carbon-carbon bonds and have been widely employed in the synthesis of complex organic molecules. Similarly, the< strong>fluoro atom can participate in various chemical transformations, including nucleophilic substitution reactions, which are crucial for modifying molecular structures.

A notable application of< strong>2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine is in the development of kinase inhibitors. Kinases are enzymes that play a pivotal role in cell signaling pathways and are often implicated in disease processes. By incorporating this compound into drug candidates, researchers can target specific kinases with high selectivity. Recent studies have demonstrated its utility in generating inhibitors that exhibit potent activity against oncogenic kinases, highlighting its potential as a lead compound in oncology drug discovery.

The< strong>hydroxymethyl group also allows for the introduction of sugar moieties or other polar functional groups, which can enhance solubility and bioavailability. This feature is particularly relevant in drug design, where pharmacokinetic properties are as important as biological activity. By leveraging the reactivity of this group, researchers can develop prodrugs or conjugates that improve delivery and efficacy.

In addition to its role in small-molecule drug discovery, 2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine has found applications in materials science and agrochemical research. Its ability to undergo diverse chemical transformations makes it a valuable precursor for synthesizing advanced materials with unique properties. For example, it can be used to create ligands for metal-organic frameworks (MOFs) or to develop novel agrochemicals that exhibit improved pest control properties.

The growing interest in< strong>2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine is reflected in the increasing number of patents and scientific publications reporting its use in synthetic chemistry and drug development. Researchers are continuously exploring new ways to utilize this compound to overcome challenges in medicinal chemistry and materials science. As our understanding of its reactivity and applications deepens, we can expect to see even more innovative uses emerge.

In conclusion,< strong>2-Bromo-3-fluoro-4-(hydroxymethyl)pyridine(CAS No: 1227601-75-3) is a multifaceted compound with significant potential across multiple domains of chemical research. Its unique structural features and reactivity make it an indispensable tool for synthetic chemists and pharmaceutical researchers alike. As advancements continue to be made in drug discovery and materials science, this compound will undoubtedly play an increasingly important role in shaping the future of these fields.

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