666175-40-2

Basic information

• Product Name: (S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ--diamine
• Synonyms: (R)-N,Nμ-Dimethyl-1,1μ-binaphthyldiamine;(S)-N,Nμ-Dimethyl-1,1μ-binaphthyldiamine;(S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ--diamine;(1S)-N,N'-Dimethyl-[1,1'-binaphthalene]-2,2'-diamine;(S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-biphthyl, (S)-N,Nμ-Dimethyl-1,1μ-biphthalene-2,2μ--diamine;(S)-N,N'-Dimethyl-1,1'-binaphthyldiamine,99%e.e.;(S)-[1,1'-Binaphthalene]-2,2'-diamine, N,N'-dimethyl
• CAS NO: 666175-40-2
• Molecular Formula: C₂₂H₂₀N₂
• Molecular Weight: 312.414
• Mol File: 666175-40-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 147-150 °C
• Boiling Point: 516.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.193±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.89±0.40(Predicted)
• CAS DataBase Reference: (S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ--diamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ--diamine(666175-40-2)
• EPA Substance Registry System: (S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ--diamine(666175-40-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 666175-40-2(Hazardous Substances Data)

Usage

General Description

(S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ--diamine are both organic chemicals known as chiral amines. They are commonly used as chiral ligands in asymmetric catalysis, particularly in the synthesis of pharmaceuticals, agrochemicals, and materials. These compounds have been found to be effective in promoting asymmetric reactions, enhancing the selectivity and efficiency of various chemical transformations. Their unique structure and stereochemistry make them valuable tools in the field of organic synthesis, enabling the production of enantiomerically pure compounds with high yields.

Upstream product

• 134627-20-6 N-(benzotriazol-1-ylmethyl)-2-naphthylamine 
• 580-13-2 2-bromonaphthalene 
• 2216-67-3 2-N-methylaminonaphthalene 
• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 93621-63-7 (R)-2,2'-bis(ethoxycarbonylamino)-1,1'-binaphthyl 

Relevant articles and documents

Electrochemical dehydrogenative cross-coupling of two anilines: Facile synthesis of unsymmetrical biaryls

A new, general ortho/para-selective anodic dehydrogenative cross-coupling of two aryl amines, naphthalen-2-amine derivatives and anilines, is described. This electrochemical protocol assembles a wide range of unsymmetrical biaryls in good to excellent yields under mild, additional-metal-catalyst-free, oxidant-free conditions with excellent selectivity, broad substrate scope, and wide functional group tolerance. This electrochemical technology is highlighted with facile incorporation of important pharmacophores into the resulting biaryls, and is applicable to the homocoupling of anilines for producing symmetrical biaryls.

Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.

Axially dissymmetric binaphthyldiimine chiral Salen-type ligands for catalytic asymmetric addition of diethylzinc to aldehyde

The axially dissymmetric chiral Schiff base ligand 10, prepared by the reaction of (R)-(+)-1,1′-binaphthyl-2,2′-diamine with (R)-(+)-2,2′-dihydroxy-[1,1′]-binaphthalenyl-3-carbaldehyde, is a fairly effective chiral ligand for the catalytic asymmetric addition reaction of diethylzinc to aldehydes.