229177-78-0

Basic information

• Product Name: (S)-5,5',6,6',7,7',8,8'-Octahydro-[1,1'-binaphthalene]-2,2'-diamine
• Synonyms: (S)-5,5',6,6',7,7',8,8'-Octahydro-[1,1'-binaphthalene]-2,2'-diamine;(1S)-5,5',6,6',7,7',8,8'-octahydro-[1,1'-Binaphthalene]-2,2'-diamine
• CAS NO: 229177-78-0
• Molecular Formula: C₂₀H₂₄N₂
• Molecular Weight: 292
• Mol File: 229177-78-0.mol

Chemical Properties

• Appearance: /
• Density: 1.156
• CAS DataBase Reference: (S)-5,5',6,6',7,7',8,8'-Octahydro-[1,1'-binaphthalene]-2,2'-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5,5',6,6',7,7',8,8'-Octahydro-[1,1'-binaphthalene]-2,2'-diamine(229177-78-0)
• EPA Substance Registry System: (S)-5,5',6,6',7,7',8,8'-Octahydro-[1,1'-binaphthalene]-2,2'-diamine(229177-78-0)

Safety Data

• Hazardous Substances Data: 229177-78-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Chiral 1,1'-binaphthyl-2,2'-diamine is utilized as a chiral ligand for the synthesis of enantiomerically pure compounds, which is essential in the development of single-enantiomer drugs. (S)-5,5',6,6',7,7',8,8'-Octahydro-[1,1'-binaphthalene]-2,2'-diamine's ability to dictate the stereochemistry of reactions ensures that the desired enantiomer is selectively produced, contributing to the efficacy and safety of pharmaceutical products.
Used in Agrochemical Industry:
In agrochemicals, chiral 1,1'-binaphthyl-2,2'-diamine is employed as a chiral catalyst to produce enantiomerically pure pesticides and other agrochemicals. This selective synthesis is vital for enhancing the effectiveness of these compounds while minimizing potential side effects on non-target organisms and the environment.
Used in Fine Chemicals Industry:
Chiral 1,1'-binaphthyl-2,2'-diamine is also used in the synthesis of fine chemicals, where the purity and stereochemistry of the product are critical. Its application in this field aids in the production of high-quality specialty chemicals used in various applications, including fragrances, dyes, and other high-value products.
Used in Organic Chemistry Research:
As a significant compound in organic chemistry, chiral 1,1'-binaphthyl-2,2'-diamine is widely used in research for the development of new synthetic methods and the exploration of asymmetric catalysis. Its unique properties make it a popular choice for studying reaction mechanisms and advancing the understanding of stereoselective processes in chemical reactions.

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 

Downstream Products

• 229177-79-1 (R)-2,2'-bis(diphenylphosphinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl 

Relevant articles and documents

Method for resolving chiral compound

The invention relates to the field of organic chemistry, in particular to a method for resolving a chiral compound. The method for splitting the chiral compound provided by the invention comprises thestep of carrying out addition reaction on a racemic compound shown as a formula A and azodicarbonic acid ester in the presence of a catalyst so as to provide an S-configuration compound shown as theformula A and an S-configuration compound shown as the formula C. According to the method, chiral phosphoric acid is used as a catalyst; good catalytic effect is achieved, and very wide substrate applicability is also achieved; the product and the recovered raw material can be obtained with excellent enantioselectivity, the selectivity coefficient of kinetic resolution can reach 371, and the method has an excellent kinetic resolution effect on various N-monosubstituted and N-unsubstituted binaphthalene diamines, H8-binaphthalene diamines and biphenyl diamines.

A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation

A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.

Process for the preparation of Binaphthylderivaten

The production of H8-1,1'-bi-2-naphthyl derivatives is by selective reduction of a binaphthyl derivative with hydrogen, together with a catalyst containing at least one metal of Pt, Ir, Os, Pd, Rh, Ru, Ni, Co and Fe on a carrier. The production of H8-1,1'

Chiral aminophosphines

This invention relates to (R)- and (S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (R-1 and S-1) and (R)- and (S)-2,2'-bis(diarylphospinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R-2 and S-2) and (R)- and (S)-2,2'-bis(dialkylphospinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R-3 and S-3); to a process for the preparation of R-1 and S-1 in which (R) or (S)-1,1'-binaphthyl-2,2'-diamine is partially hydrogenated in the presence of Adam's catalyst (5-20 wt % of starting material) at 20-100° C. for 20-100 hours in glacial acetic acid (solvent); to a process for the preparation of R-2, S-2, R-3 and S-3 in which R-1 or S-1 is reacted with chlorodiarylphosphine or chlorodialkylphosphine in the presence of n-butyllithium; and to the rhodium complexes containing 2 or 3 as effective catalysts for the asymmetric hydrogenation of prochiral substrates such as olefins to produce higher valued chiral products; and to the asymmetric catalytic hydrogenation of enamides under mild conditions using the Rh-(2) or Rh-(3) as catalyst with chemical yields as high as 100% and enantiomeric excess (e.e.) as high as 99%.