Description

6-Bromo-2-naphthyl Trifluoromethanesulfonate (CAS No. 151600-02-1) is a high-purity organic compound with the molecular formula C₁₁H₆BrF₃O₃S, widely used in advanced synthetic chemistry and pharmaceutical research. This compound features a naphthalene core substituted with a bromine atom at the 6-position and a reactive trifluoromethanesulfonate (triflate) group at the 2-position, making it a versatile intermediate for nucleophilic substitution reactions, cross-coupling reactions (e.g., Suzuki, Stille, and Negishi couplings), and other palladium-catalyzed transformations. Its triflate group is an excellent leaving group, enhancing reactivity in C-C bond-forming reactions. Suitable for laboratory-scale synthesis, this product is rigorously tested for purity and stability, ensuring optimal performance in demanding applications. Packaged under inert conditions to maintain integrity, it is ideal for researchers requiring reliable and consistent reagents for complex organic syntheses.

Properties

• CAS Number: 151600-02-1
• Complexity: 418
• IUPAC Name: (6-bromo-2-naphthyl) trifluoromethanesulfonate
• InChI: 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
• Exact Mass: 353.91731
• Molecular Formula: C11H6BrF3O3S
• Molecular Weight: 355.13
• SMILES: C1=CC2=C(C=CC(=C2)Br)C=C1OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 353.91731
• Synonyms: 6-Bromo-2-naphthyl Trifluoromethanesulfonate, 677-588-6, 151600-02-1, 6-bromonaphthalen-2-yl trifluoromethanesulfonate, (6-bromonaphthalen-2-yl) trifluoromethanesulfonate, Trifluoromethanesulfonic Acid 6-Bromo-2-naphthyl Ester, MFCD03093642, Methanesulfonic acid, 1,1,1-trifluoro-, 6-bromo-2-naphthalenyl ester, 6-Bromo-2-naphthyl trifluoromethanesulphonate, 6-bromo-2-naphthalenyl trifluoromethanesulfonate, 6-bromo-2-naphthalenyl Trifluoromethanesulphonate, 6-Bromo-2-naphthyl Triflate, SCHEMBL1195896, DTXSID80571263, AKOS025294572, BS-21540, DA-44158, SY050830, CS-0182178, T1894, 6-bromonaphthalen-2-yltrifluoromethanesulfonate, D92541, 6-bromo-2-naphtalenyl trifluoromethanesulphonate, trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester, trifluoro-methanesulfonic acid 6-bromo-naphthalen-2-yl ester

Application

6-Bromo-2-naphthyl Trifluoromethanesulfonate is a critical intermediate in the synthesis of pharmaceuticals, agrochemicals, and functional materials. Its triflate group enables efficient participation in cross-coupling reactions, facilitating the construction of complex aromatic systems. Researchers utilize this compound in palladium-catalyzed transformations to introduce naphthyl motifs into target molecules. It is also employed in the development of liquid crystals, OLED materials, and other advanced organic electronic components. The bromine substituent offers additional functionalization opportunities for further derivatization.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.