Cas no 190273-81-5 (5-Fluoroquinazolin-2-amine)

5-Fluoroquinazolin-2-amine is a fluorinated quinazoline derivative characterized by the presence of an amine group at the 2-position and a fluorine substituent at the 5-position. This structural motif imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical research. The fluorine atom enhances metabolic stability and bioavailability, while the amine group offers versatility for further functionalization. Its rigid heterocyclic core contributes to strong binding affinity in target interactions, particularly in kinase inhibition studies. The compound is commonly employed in the synthesis of bioactive molecules, including potential anticancer and antimicrobial agents, due to its favorable physicochemical profile and reactivity.
5-Fluoroquinazolin-2-amine structure
5-Fluoroquinazolin-2-amine structure
Product Name:5-Fluoroquinazolin-2-amine
CAS No:190273-81-5
MF:C8H6FN3
MW:163.151744365692
MDL:MFCD09998881
CID:115780
PubChem ID:10487209
Update Time:2025-10-09

5-Fluoroquinazolin-2-amine Chemical and Physical Properties

Names and Identifiers

    • 5-Fluoroquinazolin-2-amine
    • 2-Amino-5-fluoroquinazoline
    • 2-Quinazolinamine,5-fluoro-
    • 5-Fluoro-quinazolin-2-ylamine
    • 2-Quinazolinamine,5-fluoro-(9CI)
    • FCH880104
    • SY224207
    • PC430547
    • AX8070451
    • A924536
    • 2-Quinazolinamine, 5-fluoro-
    • CS-0155650
    • 5-Fluoroquinazolin-2-amin
    • BP-20078
    • MFCD09998881
    • AC5050
    • AKOS006302407
    • AS-59317
    • FT-0751369
    • 190273-81-5
    • DTXSID40440648
    • SCHEMBL558627
    • DB-081916
    • MDL: MFCD09998881
    • Inchi: 1S/C8H6FN3/c9-6-2-1-3-7-5(6)4-11-8(10)12-7/h1-4H,(H2,10,11,12)
    • InChI Key: NXHNWFRDSLYMON-UHFFFAOYSA-N
    • SMILES: FC1=CC=CC2C1=CN=C(N)N=2

Computed Properties

  • Exact Mass: 163.05500
  • Monoisotopic Mass: 163.05457537g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 164
  • 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: 51.8
  • XLogP3: 1.3

Experimental Properties

  • Density: 1.401
  • Boiling Point: 373.659 ℃ at 760 mmHg
  • Flash Point: 179.783°C
  • Refractive Index: 1.69
  • PSA: 51.80000
  • LogP: 1.93230

5-Fluoroquinazolin-2-amine Security Information

  • Storage Condition:Sealed in dry,2-8°C

5-Fluoroquinazolin-2-amine Pricemore >>

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Additional information on 5-Fluoroquinazolin-2-amine

Recent Advances in the Study of 5-Fluoroquinazolin-2-amine (CAS: 190273-81-5) and Its Applications in Chemical Biology and Medicine

The compound 5-Fluoroquinazolin-2-amine (CAS: 190273-81-5) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential as a versatile scaffold for drug development. This heterocyclic compound, characterized by a quinazoline core substituted with a fluorine atom at the 5-position and an amino group at the 2-position, exhibits promising pharmacological properties. Recent studies have explored its role as a kinase inhibitor, particularly targeting the epidermal growth factor receptor (EGFR) family, which is implicated in various cancers. The unique structural features of 5-Fluoroquinazolin-2-amine enable it to interact selectively with specific kinase domains, making it a valuable candidate for targeted cancer therapies.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the synthesis and biological evaluation of 5-Fluoroquinazolin-2-amine derivatives as potent EGFR inhibitors. The study employed a combination of computational docking and in vitro assays to identify the most promising candidates. Results demonstrated that certain derivatives exhibited nanomolar inhibitory activity against EGFR-TK (tyrosine kinase), with notable selectivity over other kinases. Furthermore, these compounds showed significant antiproliferative effects in non-small cell lung cancer (NSCLC) cell lines, suggesting their potential as lead compounds for further preclinical development. The study also highlighted the importance of the fluorine substitution in enhancing binding affinity and metabolic stability, underscoring the compound's utility in drug design.

Another recent advancement involves the application of 5-Fluoroquinazolin-2-amine in the development of fluorescent probes for biological imaging. A 2022 study in Chemical Communications reported the synthesis of a novel quinazoline-based fluorescent probe derived from 5-Fluoroquinazolin-2-amine. This probe demonstrated high selectivity for detecting reactive oxygen species (ROS) in live cells, providing a valuable tool for studying oxidative stress-related diseases. The probe's excellent photostability and low cytotoxicity make it suitable for long-term imaging applications, opening new avenues for diagnostic and therapeutic research.

Beyond its applications in oncology and imaging, 5-Fluoroquinazolin-2-amine has also been explored as a building block for antimicrobial agents. A 2023 study in Bioorganic & Medicinal Chemistry Letters described the synthesis of quinazoline derivatives with potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed the enhanced activity to the fluorine atom's electron-withdrawing effects, which improved the compounds' interaction with bacterial targets. These findings highlight the compound's potential in addressing the growing challenge of antibiotic resistance.

In conclusion, recent research on 5-Fluoroquinazolin-2-amine (CAS: 190273-81-5) underscores its versatility and promise in chemical biology and medicine. From its role as a kinase inhibitor in cancer therapy to its applications in imaging and antimicrobial development, this compound continues to inspire innovative research. Future studies are expected to further elucidate its mechanisms of action and optimize its derivatives for clinical translation, solidifying its position as a key player in drug discovery.

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