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
• Article Data: 12

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

General Description

The chemicals (R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl and (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamine are organic compounds with similar structures, both containing two methyl groups and diamino groups attached to binaphthyl or binaphthalene backbones. These chemicals are commonly used as chiral ligands in asymmetric synthesis reactions, as they can effectively catalyze the formation of chiral products with high enantiomeric purity. Additionally, they have been studied for their potential applications in pharmaceuticals and materials science due to their unique structural and chiral properties. Their ability to selectively influence the stereochemistry of chemical reactions makes them valuable tools in the production of important compounds with specific and desirable properties.

Upstream product

• 2216-67-3 2-N-methylaminonaphthalene 
• 580-13-2 2-bromonaphthalene 
• 134627-20-6 N-(benzotriazol-1-ylmethyl)-2-naphthylamine 
• 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 
• 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

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.

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.