Description

(S)-(+)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate) (CAS No. 126613-06-7) is a highly specialized chiral reagent with the molecular formula C₂₂H₁₂F₆O₆S₂. This enantiomerically pure compound is derived from (S)-(+)-1,1′-Bi-2-naphthol (BINOL) and features two trifluoromethanesulfonate (triflate) groups, making it an excellent chiral catalyst or auxiliary in asymmetric synthesis. Its rigid binaphthyl backbone ensures high stereoselectivity, while the triflate groups serve as excellent leaving groups for nucleophilic substitution reactions. This compound is widely utilized in organic synthesis, pharmaceuticals, and materials science due to its ability to induce chirality in complex molecular frameworks. Packaged under inert conditions to ensure stability and purity, it is ideal for researchers requiring precise enantiomeric control.

Properties

• CAS Number: 126613-06-7
• Complexity: 904
• IUPAC Name: [1-[2-(trifluoromethylsulfonyloxy)-1-naphthyl]-2-naphthyl] trifluoromethanesulfonate
• InChI: InChI=1S/C22H12F6O6S2/c23-21(24,25)35(29,30)33-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)34-36(31,32)22(26,27)28/h1-12H
• InChI Key: OYJLCOSEYYZULE-UHFFFAOYSA-N
• Exact Mass: 549.99794942
• Molecular Formula: C22H12F6O6S2
• Molecular Weight: 550.5
• SMILES: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)OS(=O)(=O)C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Topological: 104
• Monoisotopic Mass: 549.99794942
• Synonyms: (S)-(+)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate), 1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate), 2,2′-bis(trifluoromethanesulfonyloxy)-1,1′-binaphthyl, 603-279-2, 603-283-4, 126613-06-7, 128544-05-8, 128575-34-8, (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), (R)-(-)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate), (S)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), [1,1′-binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), MFCD00274615, (R)-(-)-1,1′-Binaphthol-2,2′-bis(trifluoromethanesulfonate), C22H12F6O6S2, [1-[2-(trifluoromethylsulfonyloxy)naphthalen-1-yl]naphthalen-2-yl] trifluoromethanesulfonate, NSC686511, NSC 686511, (S)-[1,1-Binaphthalene]-2,2-diyl bis(trifluoromethanesulfonate), (R)-(-)-1,1′-Binaphthyl-2,2′-diyl Bis(trifluoromethanesulfonate), (S)-(+)-1,1′-Binaphthyl-2,2′-diyl Bis(trifluoromethanesulfonate), Methanesulfonic acid, trifluoro-, (1,1′-binaphthalene)-2,2′-diyl ester, Methanesulfonic acid, 1,1,1-trifluoro-, 1,1′-(1S)-[1,1′-binaphthalene]-2,2′-diyl ester, (S)-(+)-1,1/’-Binaphthol-2,2/’-bis(trifluoromethanesulfonate), (R)-(-)-1,1/’-Binaphthol-2,2/’-bis(trifluoromethanesulfonate), (S)-(+)-1,1′-Binaphthol-2,2′-bis(trifluoromethanesulfonate), Methanesulfonic acid, trifluoro-, [1,1′-binaphthalene]-2,2′-diyl ester, (S)-(+)-1,1-Binaphthol-2,2-Bis(Trifluoromethanesulfonate), (R)-1,1′-Binaphthyl-2,2′-diyl bis(trifluoromethane)sulphonate, (R)-(-)-1,1′-Bi-2-naphthyl bis-trifluoromethanesulfonate, SCHEMBL635407, (S)-1,1′-Bi(2-naphthol) bis(trifluoromethanesulfonate), CHEMBL1984394, DTXSID10155257, BCP32264, AKOS015889276, AC-8072, AC-8073, CS-W013808, NSC-686511, [1-[2-(trifluoromethylsulfonyloxy)-1-naphthyl]-2-naphthyl] trifluoromethanesulfonate, BS-14878, NCI60_031201, B2230, B2231, CS-0031304, D88910, E77910, F81722, A805933, 1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate), 97%, 2,2′-bis(trifluoromethanesulfonyl-oxy)-1,1′-binaphthyl, 1,1′-Binaphthyl-2,2′-diyl bis(trifluoromethanesulphonate), 2,2′-bis(trifluoromethanesulfonyloxy)-1,1′-binaphthalene, (R)-(-)-1,1”-Binaphthol-2,2”-bis(trifluoromethanesulfonate), (R)-(-)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate), 97%, (R)-(-)-1,1′-Binaphthol-2,2′-bis(trifluoromethanesulfonate), (R)-(-9-1,1′-Binaphthyl-2,2′-diyl bis(trifluoromethanesulfonate), (S)-(+)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate), 97%, (S)-1,1′-Binaphthalene-2,2′-diyl bis(trifluoromethanesulfonate), (R)-(-)-1,1′-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE), Methanesulfonic acid, 1,1,1-trifluoro-, 1,1′-[1,1′-binaphthalene]-2,2′-diyl ester, Methanesulfonic acid,1,1,1-trifluoro-,1,1′-[1,1′-binaphthalene]-2,2′-diyl ester, [1-[2-(trifluoromethylsulfonyloxy)naphthalen-1-yl]naphthalen-2-yl] tris(fluoranyl)methanesulfonate, trifluoromethanesulfonic acid [1-[2-(trifluoromethylsulfonyloxy)-1-naphthalenyl]-2-naphthalenyl] ester

Application

This compound is extensively used as a chiral catalyst or ligand in asymmetric synthesis, particularly in C-C bond-forming reactions. It is valuable in pharmaceutical research for the synthesis of enantiomerically pure drugs and intermediates. Additionally, it serves as a precursor for chiral polymers and advanced materials requiring optical activity.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1B (100%)
• Eye Dam. 1 (100%)

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