80655-81-8 Usage
Description
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol is a chiral compound derived from 1,1'-bi-2-naphthol, featuring two bromine atoms at the 6,6' positions. It exhibits specific stereochemistry, with the S configuration, which is crucial for its applications in various chemical reactions and synthesis processes.
Uses
Used in Pharmaceutical Synthesis:
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol is used as a key intermediate in the synthesis of (2R,3S)-3-phenylisoserine hydrochloride, a compound with potential pharmaceutical applications. Its unique stereochemistry and bromine substituents enable selective reactions and the formation of desired chiral products.
Used in Chiral Ligand Synthesis:
In the field of asymmetric catalysis, (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol is used as a precursor for the synthesis of BINOL-derived chiral ligands with aryl substituents in the 6,6-positions. These ligands are essential for enantioselective reactions, allowing the production of chiral molecules with high selectivity and purity, which are vital in the development of pharmaceuticals and agrochemicals.
Used in Chemical Research:
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol serves as a valuable compound for research purposes, particularly in the study of stereochemistry, asymmetric synthesis, and the development of new synthetic methodologies. Its unique structural features and reactivity make it an attractive candidate for exploring novel chemical reactions and applications.
Reactions
Ligand used to prepare a chiral zirconium catalyst useful in asymmetric Strecker reactions.
Ligand used in the zinc-catalyzed enantioselective Hetero Diels-Alder reaction.
Ligand used in asymmetric Friedel-Crafts reactions of pyrroles with glyoxylates.
Check Digit Verification of cas no
The CAS Registry Mumber 80655-81-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,0,6,5 and 5 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 80655-81:
(7*8)+(6*0)+(5*6)+(4*5)+(3*5)+(2*8)+(1*1)=138
138 % 10 = 8
So 80655-81-8 is a valid CAS Registry Number.
80655-81-8Relevant articles and documents
Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
Yu, Jeong Jae,Ryoo, Jae Jeong
, p. 587 - 596 (2022/01/20)
Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols
Liu, Wen-Bo,Usman, Muhammad,Wu, Lin-Yang
, (2020/02/25)
An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.
Novel π-expanded chrysene-based axially chiral molecules: 1,1′-bichrysene-2,2′-diols and thiophene analogs
An, Shujie,Liu, Qiancai,Ma, Li,Tang, Guofeng,Zhong, Yaling
, p. 641 - 645 (2020/05/25)
1,1′-Bichrysene-2,2′-diol and its thiophene analogs, 6,6′-biphenanthro-[1,2-b]thiophene-7,7′-diols, as a series of novel π-expanded chrysene-/phenanthro[1,2-b]thiophene-based axially chiral molecules are synthesized from 1,1′-bi-2-naphthols with key steps
