93713-30-5

Basic information

• Product Name: (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine
• Synonyms: (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine;(1R)-N,N'-Dimethyl-[1,1'-binaphthalene]-2,2'-diamine;(R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-biphthyl, (R)-N,Nμ-Dimethyl-1,1μ-biphthalene-2,2μ-diamine;(R)-[1,1'-Binaphthalene]-2,2'-diamine, N,N'-dimethyl
• CAS NO: 93713-30-5
• Molecular Formula: C₂₂H₂₀N₂
• Molecular Weight: 312.4076
• Mol File: 93713-30-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• BRN: 5588762
• CAS DataBase Reference: (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine(93713-30-5)
• EPA Substance Registry System: (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine(93713-30-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 93713-30-5(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
(R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are used as chiral ligands for [their role in asymmetric synthesis] because of [their ability to catalyze the formation of chiral products with high enantiomeric purity].
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are used as [chiral building blocks or catalysts] for [their potential to contribute to the development of enantiomerically pure drugs, which can have significant implications for drug efficacy and safety].
Used in Materials Science:
(R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are utilized in materials science as [chiral dopants or components] for [their unique structural and chiral properties that can enhance or modify the properties of various materials].

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 74538-22-0 α-bromo N-methyl propionamide 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 
• 134627-20-6 N-(benzotriazol-1-ylmethyl)-2-naphthylamine 
• 580-13-2 2-bromonaphthalene 
• 2216-67-3 2-N-methylaminonaphthalene 
• 93621-63-7 (R)-2,2'-bis(ethoxycarbonylamino)-1,1'-binaphthyl 

Relevant articles and documents

Synthesis and Conformational Studies of a Chiral Octadentate Ligand Derived from (R)-1,1′-Binaphthyl-2,2′-diamine and its Dinuclear Zinc(II) and Nickel(II) Complexes

The synthesis of the octadentate ligand (R)-(-)-N,N′ -dimethyl-N,N′-bis{3-[bis(1-methyl-2-benzimidazolylmethyl)]-aminopropyl} -1,1′-binaphthyl-2,2′-diamine (L), containing a central 1,1′-binaphthalenediamine core connected to two aminobis(benzimidazole) arms by flexible trimethylene carbon chains, and its dinuclear complexes [Zn2L](ClO4)4 and [Ni2L](ClO 4)4 is reported. The structural features of the free ligand and the metal complexes have been investigated by NMR, UV/Visible, CD, and computational methods, including simulated annealing-molecular mechanics and semiempirical PM3 calculations. The preferred conformation of the free ligand is characterized by a relatively small dihedral angle of about 75° between the two naphthyl rings, which is imposed by favorable stacking interactions between benzimidazole rings from different arms. In the dinuclear zinc(II) complex each metal ion is pseudotetrahedral and bound to three N donors of one aminobis(benzimidazole) arm and one N donor of the binaphthalenediamine residue. Coordination of the benzimidazole groups to the metal ions prevents the stacking interactions seen in the free ligand and, consequently, the dihedral angle between the naphthyl groups increases to the more usual ca. 90°. In the dinuclear nickel(II) complex, the hgand still provides four nitrogen donors to each metal centers, but the stereochemical preference of the nickel(II) ions imposes a ligand field of tetragonal symmetry, with pseudo-octahedral metal centers, and this occurs with pronounced flattening of the dihedral angle between the naphthyl groups. The change in conformation, from L to [Zn2L]4+ to [Ni2L] 4+, of the critical 1,1′-binaphthalenediamine residue is clearly indicated by CD spectra. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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.

Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination

Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec

Chiral aromatic amine compounds and preparation method thereof

The invention discloses chiral aromatic amine compounds and a preparation method thereof. The chiral aromatic amine compounds are characterized in that under the alkaline condition, compounds I reactwith compounds II to obtain corresponding products, namely chiral aromatic amine compounds labeled by compounds with structural formulas III, IV and V or enantiomers, despinners, diastereoisomers or isotopes thereof: (the formula is shown in the description), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and R17 are separately selected from any group, and X is chlorine or bromine. The chiral aromatic amine compounds with high optical purity (an ee value is greater than 99 percent) have wide application in the fields of bioactivity, materials, chiral ligands, chiral catalysts and the like, and can be further derived to prepare recemic or chiral aromatic amine ligands serving as catalyst for asymmetric catalytic reaction. The invention lays a foundation for developing novel catalysts for the asymmetric catalytic reaction and has economic practicality and industrial application prospect.

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.