(S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide

Base Information

• Chemical Name: (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide
• CAS No.: 1010800-00-6
• Molecular Formula: C₄₁H₂₅F₃NO₅PS
• Molecular Weight: 731.688
• Mol file: 1010800-00-6.mol

Synonyms:

Chemical Property of (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: (S)-[3,3’-di(1-naphthyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide is a chiral BINOL-based N-triflylphosphoramide, recognized as a highly acidic, metal-free Bronsted acid catalyst. Its strong acidity and structural rigidity, derived from the binaphthyl backbone and triflyl group, make it effective for asymmetric catalysis, particularly in reactions requiring robust chiral acid promoters. (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide’s design leverages the steric and electronic properties of the naphthyl substituents to enhance enantioselectivity and reactivity.

Technology Process of (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide

There total 3 articles about (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(S)-[2,2':4',1'':3'',2'''-quaternaphthalene]-2'',3'-diol (851615-07-1,863659-88-5) + (N-trichlorophosphoranylidene)trifluoromethanesulfonamide (28048-16-0) → (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide (1010800-00-6)

Guidance literature:

(S)-[2,2':4',1'':3'',2'''-quaternaphthalene]-2'',3'-diol; (N-trichlorophosphoranylidene)trifluoromethanesulfonamide; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

With water; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1055/s-0036-1588782

Reference yield:

Trifluoromethanesulfonamide (421-85-2) + (S)-[2,2':4',1'':3'',2'''-quaternaphthalene]-2'',3'-diol (851615-07-1,863659-88-5) → (S)-[3,3’-di(1-naphtyl)-1,1’-binaphthalen-2,2’-yl]-N-triflyl phosphoramide (1010800-00-6)

Guidance literature:

(S)-[2,2':4',1'':3'',2'''-quaternaphthalene]-2'',3'-diol; With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.166667h;

With trichlorophosphate; In dichloromethane; at 20 ℃; for 1.083h;

Trifluoromethanesulfonamide; In dichloromethane; acetonitrile; for 12h; Reflux;

DOI:10.1002/cjoc.201900544

Reference yield:

Trifluoromethanesulfonamide (421-85-2) + (R)-3,3'-di(1-naphthyl)-1,1'-binaphthyl-2,2'-diyl phosphoryl chloride → C41H25F3NO5PS (1010800-00-6)

Guidance literature:

In propiononitrile; Reflux;

DOI:10.1002/chem.201001438

upstream raw materials:

(S)-[2,2':4',1'':3'',2'''-quaternaphthalene]-2'',3'-diol

(N-trichlorophosphoranylidene)trifluoromethanesulfonamide

Trifluoromethanesulfonamide