Cas no 151600-02-1 (6-Bromo-2-naphthyl Trifluoromethanesulfonate)

6-Bromo-2-naphthyl Trifluoromethanesulfonate is a versatile aryl triflate derivative commonly employed in cross-coupling reactions, such as Suzuki and Stille couplings, due to its high reactivity as an electrophile. The presence of both a bromo substituent and a trifluoromethanesulfonate (triflate) group on the naphthalene ring enhances its utility in sequential functionalization, enabling selective transformations. Its stability under standard conditions and compatibility with a range of catalysts make it a valuable intermediate in pharmaceutical and materials science research. The electron-withdrawing triflate group facilitates efficient nucleophilic displacement, while the bromo moiety offers additional reactivity for further derivatization. This compound is particularly useful for constructing complex polycyclic aromatic systems.
6-Bromo-2-naphthyl Trifluoromethanesulfonate structure
151600-02-1 structure
Product Name:6-Bromo-2-naphthyl Trifluoromethanesulfonate
CAS No:151600-02-1
MF:C11H6BrF3O3S
MW:355.12775182724
MDL:MFCD03093642
CID:99494
PubChem ID:87577607
Update Time:2025-06-26

6-Bromo-2-naphthyl Trifluoromethanesulfonate Chemical and Physical Properties

Names and Identifiers

    • Methanesulfonic acid,1,1,1-trifluoro-, 6-bromo-2-naphthalenyl ester
    • 6-Bromo-2-naphthyl Trifluoromethanesulfonate
    • (6-bromonaphthalen-2-yl) trifluoromethanesulfonate
    • 6-BROMO-2-NAPHTHYL TRIFLUOROMETHANESULPHONATE
    • 2-Trifluoromethanesulfonyloxy-6-bromonaphthalene
    • 6-bromo-2-naphthalenyl trifluoromethanesulfonate
    • 6-bromo-2-naphthalenyl trifluoromethanesulphonate
    • 6-Bromo-2-naphthyl Triflate
    • 6-bromonaphthalen-2-yl trifluoromethanesulfonate
    • PC2463
    • Trifluoromethanesulfonic Acid 6-Bromo-2-naphthyl Ester
    • trifluoromethanesulfonic acid 6-bromonaphthalen-2-yl ester
    • 6-Bromo-2-naphthyl Triflate Trifluoromethanesulfonic Acid 6-Bromo-2-naphthyl Ester
    • FT-0725553
    • SCHEMBL1195896
    • trifluoro-methanesulfonic acid 6-bromo-naphthalen-2-yl ester
    • Methanesulfonic acid, 1,1,1-trifluoro-, 6-bromo-2-naphthalenyl ester
    • CS-0182178
    • 151600-02-1
    • MFCD03093642
    • A809195
    • trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester
    • SY050830
    • BS-21540
    • T1894
    • 6-bromonaphthalen-2-yltrifluoromethanesulfonate
    • AKOS025294572
    • D92541
    • 6-bromo-2-naphtalenyl trifluoromethanesulphonate
    • DTXSID80571263
    • DA-44158
    • MDL: MFCD03093642
    • Inchi: 1S/C11H6BrF3O3S/c12-9-3-1-8-6-10(4-2-7(8)5-9)18-19(16,17)11(13,14)15/h1-6H
    • InChI Key: FRNRXKFDZXFNKG-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2C=C(C=CC=2C=1)OS(C(F)(F)F)(=O)=O

Computed Properties

  • Exact Mass: 353.91700
  • Monoisotopic Mass: 353.91731g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 3
  • Complexity: 418
  • 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
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 4.6
  • Topological Polar Surface Area: 51.8?2

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 52.0 to 56.0 deg-C
  • PSA: 51.75000
  • LogP: 4.91150
  • Solubility: Not determined

6-Bromo-2-naphthyl Trifluoromethanesulfonate Security Information

6-Bromo-2-naphthyl Trifluoromethanesulfonate Customs Data

  • HS CODE:2906299090
  • Customs Data:

    China Customs Code:

    2906299090

    Overview:

    2906299090 Other aromatic alcohols. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2906299090 other aromatic alcohols.Supervision conditions:None.VAT:17.0%.Tax rebate rate:9.0%.MFN tariff:5.5%.General tariff:30.0%

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6-Bromo-2-naphthyl Trifluoromethanesulfonate Production Method

Additional information on 6-Bromo-2-naphthyl Trifluoromethanesulfonate

Introduction to 6-Bromo-2-naphthyl Trifluoromethanesulfonate (CAS No. 151600-02-1)

6-Bromo-2-naphthyl Trifluoromethanesulfonate, with the CAS number 151600-02-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the class of naphthalene derivatives, characterized by the presence of a bromine substituent at the 6-position and a trifluoromethanesulfonate (triflate) group at the 2-position. The unique structural features of this molecule make it a valuable intermediate in synthetic chemistry, particularly in the development of biologically active molecules.

The trifluoromethanesulfonate group is a key functional moiety that enhances the reactivity and stability of the compound, making it particularly useful in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. These reactions are fundamental in constructing complex organic frameworks, which are often required in the synthesis of pharmaceuticals and agrochemicals. The bromine substituent at the 6-position of the naphthalene ring further contributes to its utility as a synthetic building block, allowing for further functionalization via palladium-catalyzed reactions.

In recent years, there has been a surge in research focused on developing novel therapeutic agents derived from naphthalene derivatives. The structural motif of naphthalene is known for its ability to interact with biological targets such as enzymes and receptors, making it a privileged scaffold in drug discovery. Specifically, 6-Bromo-2-naphthyl Trifluoromethanesulfonate has been explored in the synthesis of small-molecule inhibitors targeting various diseases, including cancer and inflammatory disorders. Its versatility in serving as a precursor for more complex molecules has made it a staple in medicinal chemistry libraries.

One of the most compelling applications of 6-Bromo-2-naphthyl Trifluoromethanesulfonate is in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and their dysregulation is often associated with diseases such as cancer. By designing molecules that selectively inhibit specific kinases, researchers can develop targeted therapies with improved efficacy and reduced side effects. The triflate group in this compound facilitates its conversion into boronic acids or azides, which are commonly used in kinase inhibitor synthesis. For instance, recent studies have demonstrated its utility in generating novel inhibitors of tyrosine kinases, which have shown promise in preclinical trials.

Another area where 6-Bromo-2-naphthyl Trifluoromethanesulfonate has found utility is in the synthesis of fluorescent probes for biological imaging. Fluorescent compounds are essential tools in biomedical research for visualizing cellular processes and diagnosing diseases. The naphthalene core of this molecule can be modified to produce luminescent probes that emit light at specific wavelengths, allowing researchers to track biological events with high precision. Recent advancements in this field have shown that derivatives of 6-Bromo-2-naphthyl Trifluoromethanesulfonate can be used to develop probes that selectively label specific proteins or nucleic acids, providing new insights into cellular mechanisms.

The synthetic methodologies involving 6-Bromo-2-naphthyl Trifluoromethanesulfonate have also seen significant advancements. Modern synthetic techniques, such as flow chemistry and microwave-assisted synthesis, have enabled more efficient and scalable production of this compound. These methods not only improve yield but also reduce waste, aligning with the growing emphasis on green chemistry principles. For example, recent studies have reported the use of flow chemistry to perform cross-coupling reactions involving 6-Bromo-2-naphthyl Trifluoromethanesulfonate under mild conditions, resulting in high yields and minimal byproducts.

The pharmaceutical industry has been particularly keen on exploring derivatives of 6-Bromo-2-naphthyl Trifluoromethanesulfonate due to their potential therapeutic applications. Several drug candidates derived from this compound have entered clinical trials, demonstrating their safety and efficacy in treating various conditions. One notable example is its use in developing antiviral agents. The ability of naphthalene derivatives to interfere with viral replication has been exploited to create novel antiviral drugs. Preliminary studies have shown that compounds based on 6-Bromo-2-naphthyl Trifluoromethanesulfonate exhibit potent antiviral activity against several strains of RNA viruses.

In conclusion, 6-Bromo-2-naphthyl Trifluoromethanesulfonate (CAS No. 151600-02-1) is a versatile and valuable compound with numerous applications in pharmaceutical research and chemical synthesis. Its unique structural features make it an excellent intermediate for constructing biologically active molecules, particularly kinase inhibitors and fluorescent probes. The ongoing research into its derivatives continues to uncover new possibilities for treating diseases such as cancer and viral infections. As synthetic methodologies continue to evolve, the utility of 6-Bromo-2-naphthyl Trifluoromethanesulfonate is expected to expand even further, solidifying its place as a cornerstone in modern chemical biology.

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