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

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

Uses

Used in Pharmaceutical Industry:
(S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are used as chiral ligands in asymmetric catalysis for the synthesis of pharmaceuticals. They promote asymmetric reactions, enhancing the selectivity and efficiency of chemical transformations, which is crucial for the production of enantiomerically pure compounds with high yields. This ensures the desired biological activity and minimizes potential side effects of the resulting pharmaceuticals.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are employed as chiral ligands in asymmetric catalysis for the synthesis of agrochemicals. Their ability to promote asymmetric reactions allows for the selective production of enantiomerically pure compounds, which is essential for the development of effective and environmentally friendly agrochemicals with minimal off-target effects.
Used in Materials Science:
(S)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (S)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are also used in materials science as chiral ligands in asymmetric catalysis for the synthesis of chiral materials. Their unique structure and stereochemistry enable the production of enantiomerically pure materials with specific properties, such as optical activity, chiral recognition, and self-assembly capabilities. These materials have potential applications in various fields, including sensors, catalysts, and chiral separation techniques.

Upstream product

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

Downstream Products

• 173847-41-1 2,2'-bis-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.

Aerobic oxidative homocoupling of aryl amines using heterogeneous rhodium catalysts

The first heterogeneous catalyzed oxidative coupling of aryl amines is reported. Aryl amines were dimerized at room temperature under air using a heterogeneous Rh/C catalyst in the presence of acids. By choosing a suitable acidic solvent, biaryl compounds and carbazoles were selectively prepared in good yields. This reaction is operationally simple and provides an effi cient synthetic methodology for the preparation of biaryl diamines via oxidative C - H activation.

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.

An efficient intermolecular C(aryl)-S bond forming reaction catalyzed by BINAM-copper(II) complex

A wide range of diaryl thioethers and aryl alkyl thioethers are synthesized from the corresponding aryl iodides and aromatic/aliphatic thiols through Ullmann type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-Cu(OTf)2 complex. Less reactive aryl bromides have also been shown to react with thiols under identical reaction conditions to give good yields of the thioethers without increasing the reaction temperature and time.

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.

Solution Conformation of Two C2-Symmetric Amino Derivatives of 1,1'-Binaphthalene by Circular Dichroism and Liquid Crystal Technique

The solution conformation of two C2-symmetric 1,1'-binaphthyl compounds (N,N,N',N'-tetramethyl--2,2'-diamine (1) and N,N'-dimethyl--2,2'-diamine (2)) has been studied by MMX calculations, analysis of the adsorption and CD spectra, and induction of cholesteric mesophases in nematic liquid crystals.All these methods indicate that 1 prefers a cisoid conformation and that 2 assumes a conformation where the two naphthyl moieties are quasi-perpendicular.

Use of Carboxylic Acids as Chiral Solvating Agents for the Determination of Optical Purity of Chiral Amines by NMR Spectroscopy

Optically pure mandelic acid, Mosher's acid, and N-(3,5-dinitrobenzoyl)phenylglycine have been used as chiral solvating agents to induce nonequivalence in the 1H NMR spectra of several diamines, amino acid esters, amino alcohols, and other amines.The identity of the chiral solvating agent and the stoichiometry of the solvation complexes that yield the greatest nonequivalence varies with the nature of the substrate.

AXIALLY DISSYMMETRIC bis(AMINOPHOSPHINE)S DERIVED FROM 2,2 prime -DIAMINO-1,1 prime -BINAPHTHYL. SYNTHESIS AND APPLICATION TO RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATIONS.

Axially dissymmetric bisphosphine ligands, (R)- and (S)-2,2 prime -bis(diphenylphosphinoamino)-1,1 prime -binaphthyl (BDPAB) and (R)-2,2 prime -bis left bracket N-(diphenylphosphino)methylamino right bracket -1,1 prime -binaphthyl (Me-BDPAB) were conveniently prepared from 2,2 prime -diamino-1,1 prime -binaphthyl. The rhodium(I)-catalyzed asymmetric hydrogenation of alpha -acylamidoacrylic acids and esters gave the corresponding amino acids of up to 95% optical purity. The sign of the centro-chirality of the product amino acids was always the same to that of axial chirality of the ligand in both cases of BDPAB and Me-BDPAB.