Description

1,1′-(2,7-Naphthalenediyl) bis(1,1,1-trifluoromethanesulfonate) (CAS No. 151391-00-3) is a high-purity, specialized organic compound with the molecular formula C₁₂H₆F₆O₆S₂. This bifunctional triflate derivative features a naphthalene core symmetrically substituted with two trifluoromethanesulfonate (triflate) groups at the 2- and 7-positions, making it an excellent electrophilic reagent for advanced organic synthesis and cross-coupling reactions. Its IUPAC name is [7-(trifluoromethylsulfonyloxy)naphthalen-2-yl] trifluoromethanesulfonate. The compound is supplied as a crystalline solid with exceptional stability under inert conditions, ensuring reliable performance in sensitive applications. Ideal for researchers in pharmaceuticals, materials science, and catalysis, this product undergoes rigorous QC testing (HPLC, NMR) to guarantee ≥98% purity. Store in a cool, dry place under argon to maintain reactivity.

Properties

• CAS Number: 151391-00-3
• Complexity: 642
• IUPAC Name: [7-(trifluoromethylsulfonyloxy)-2-naphthyl] trifluoromethanesulfonate
• InChI: InChI=1S/C12H6F6O6S2/c13-11(14,15)25(19,20)23-9-3-1-7-2-4-10(6-8(7)5-9)24-26(21,22)12(16,17)18/h1-6H
• InChI Key: NWUWLVCEYBABOV-UHFFFAOYSA-N
• Exact Mass: 423.95099923
• Molecular Formula: C12H6F6O6S2
• Molecular Weight: 424.3
• SMILES: C1=CC(=CC2=C1C=CC(=C2)OS(=O)(=O)C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Topological: 104
• Monoisotopic Mass: 423.95099923
• Synonyms: 151391-00-3, 2,7-Naphthalenebis(trifluoromethanesulfonate), DTXSID701174194, DTXCID301605581, 1,1′-(2,7-Naphthalenediyl) bis(1,1,1-trifluoromethanesulfonate), 834-003-0, naphthalene-2,7-diyl bis(trifluoromethanesulfonate), 2,7-Bis(trifluoromethanesulfonyloxy)naphthalene, methanesulfonic acid, trifluoro-, 2,7-naphthalenediyl ester, [7-(trifluoromethylsulfonyloxy)naphthalen-2-yl] trifluoromethanesulfonate, MFCD20260329, 2,7-Naphthaleneditriflate, SCHEMBL598333, AKOS040768589, BS-45860, N1071, D91778, 2,7-bis(trifluoromethane sulfonyloxy)naphthalene, 2,7-bis(trifluoromethanesulfonyloxy) naphthalene, naphthalene-2,7-diylbis(trifluoromethanesulfonate), naphthalene-2,7-diyl bis(trifluoromethane sulfonate), [7-(trifluoromethylsulfonyloxy)-2-naphthyl] trifluoromethanesulfonate, 1,1a(2)-(2,7-Naphthalenediyl) bis(1,1,1-trifluoromethanesulfonate), Trifluoro-methanesulfonic acid 7-(trifluoro-methanesulfonyloxy)-naphthalene-2-yl ester

Application

This compound serves as a versatile building block in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Heck) due to its highly reactive triflate leaving groups. It enables the synthesis of extended π-conjugated systems for organic electronics such as OLEDs and OFETs. The naphthalene backbone facilitates rigid, planar architectures in polymer and small-molecule semiconductors. Researchers also employ it to create fluorescent probes and ligands for metal-organic frameworks (MOFs).

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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