(S)-(+)-1,1′-Binaphthol-2,2′-bis(trifluoromethanesulfonate)
(S)-(+)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate) (CAS 128544-05-8) is a white to light yellow crystalline powder melting at about 83 to 85 degrees Celsius, classified as corrosive to skin, eyes and metals and described as stable only when protected from moisture. It is the bis(triflate) ester of (S)-1,1′-bi-2-naphthol, a C2-symmetric axially chiral scaffold in which both naphthol oxygens have been converted into highly electrophilic trifluoromethanesulfonate leaving groups. That activation makes the ring positions excellent electrophiles and coupling partners while the single-enantiomer form delivers perfectly defined axial chirality. Because the binaphthyl axis is the only chiral element, the compound is prized as a versatile chiral building block, derivatising reagent and ligand precursor for asymmetric synthesis.
1. Chiral ligand and catalyst synthesis: it is the key precursor for BINAP, BINOL-derived phosphoramidites, monophosphites and other axially chiral ligand libraries used in asymmetric hydrogenation, allylic substitution, hydroformylation, Pauson-Khand and organocatalytic transformations.
2. Cross-coupling and functionalisation partner: the reactive triflate groups allow palladium- or nickel-catalysed coupling, borylation, cyanation, amination, alkynylation and carbonylation to install substituents directly on the binaphthyl core without racemisation, opening access to bulky chiral scaffolds that are difficult to build otherwise.
3. Analytical and separation applications: used to prepare chiral derivatising agents, chiral stationary phase precursors and NMR shift reagents for determining the enantiomeric purity of alcohols, amines and diols, and as a reference compound in chiral method development and enantioselective assay validation.
4. Handling and storage: corrosive, moisture sensitive and lachrymatory; manipulate in a glovebox or under dry nitrogen, keep containers sealed and refrigerated, use anhydrous solvents, and store away from water, alcohols, amines, bases and oxidising agents to avoid hydrolysis of the triflate groups.
Product Name: (S)-(+)-1,1′-Binaphthol-2,2′-bis(trifluoromethanesulfonate)
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