TCI D4663 N-[(11bS)-4,5-Dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-2-yl]trifluoromethanesulfonamide is a high-molecular-weight chiral compound built on a dinaphthoazepine framework — a binaphthyl system bridged by an azepine ring — and carrying a trifluoromethanesulfonamide group as its principal functional group. The (11bS) stereochemical descriptor indicates that the material is supplied as a single enantiomer with axial chirality. In the laboratory, compounds of this class generally serve in asymmetric chemistry, acting as organocatalysts, as pre-catalysts, or as intermediates for the preparation of advanced-generation chiral catalysts.
The characteristic that makes this material valuable is the combination of a rigid binaphthyl backbone with a trifluoromethyl-substituted sulfonamide group. The binaphthyl framework provides a clearly defined steric environment around the reaction centre, so that it can differentiate between the two faces of a substrate and deliver products with enantiomeric excess. The trifluoromethanesulfonamide group, meanwhile, is strongly electron-withdrawing, making the N–H proton considerably more acidic and allowing it to act as a strong hydrogen-bond donor or as a weak Brønsted acid — two activation modes that form the backbone of modern organocatalysis.
In Indonesian laboratories, a reagent of this type is typically used in academic and industrial research groups working on asymmetric synthesis, methodology development, and the preparation of enantiomerically enriched building blocks. It is generally handled on a small scale at the bench, weighed out under controlled conditions, and used in exploratory catalyst screening or in reaction optimisation work where control of stereochemistry is the primary objective rather than bulk production volume.
- Asymmetric organocatalysis — the single-enantiomer binaphthyl framework creates a defined chiral pocket that allows the catalyst to differentiate substrate faces and generate products with enantiomeric excess.
- Chiral catalyst synthesis — the compound serves as an intermediate or pre-catalyst from which more elaborate, advanced-generation chiral catalyst systems can be constructed in the laboratory.
- Hydrogen-bond-donor activation — the strongly electron-withdrawing trifluoromethanesulfonamide group makes the N–H proton acidic enough to bind and activate substrates through strong hydrogen bonding.
- Brønsted acid catalysis — because the sulfonamide N–H behaves as a weak Brønsted acid, the material supports proton-transfer activation modes widely used in modern asymmetric methodology.
- Methodology and screening studies — research groups developing new enantioselective reactions use this reagent in catalyst screening panels to evaluate stereochemical control across different substrate classes.
| Brand | TCI |
|---|---|
| CAS number | 871915-77-4 |
| Molecular formula | — |
| Purity | — |
| Category | TCI |
| Pack sizes | please refer to the manufacturer's catalogue listing and the accompanying label for the pack sizes available and the recommended storage condition |
| Physical form | — |
| Storage | — |
- Chemical name: N-[(11bS)-4,5-Dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-2-yl]trifluoromethanesulfonamide
- Stereochemistry: supplied as a single enantiomer, (11bS) configuration, axially chiral
Store the container tightly closed in a cool, dry, well-ventilated place, away from direct sunlight, moisture, and sources of heat or ignition, and follow the storage condition stated on the product label and Safety Data Sheet. Keep the material in its original manufacturer container, or in a clean, chemically compatible, clearly labelled vessel if transfer is necessary. Handle in a fume hood using appropriate personal protective equipment, including safety goggles, gloves, and a laboratory coat. Avoid raising dust, and avoid contact with skin, eyes, and clothing. Weigh out only the quantity required, close the container promptly afterwards to limit exposure to atmospheric moisture, and dispose of residues and contaminated materials in accordance with the applicable chemical waste procedures of your institution.
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![871915-77-4 N-[(11bS)-4,5-Dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-2-yl]trifluoromethanesulfonamide - AMI Scientific](http://amiscientific.com/cdn/shop/files/TCI2510D4663.jpg?v=1767107810&width=1445)