4488-22-6

Usage

Uses

Used in Chemical Synthesis:
(S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE is used as a ligand in the synthesis of novel axially chiral Rh N-heterocyclic carbene complexes. These complexes are applied in the Rh-catalyzed enantioselective hydrosilylation of methyl ketones, a process that is crucial for creating chiral molecules with specific configurations.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE is used as a catalyst in the enantioselective direct aldol reaction. This reaction, organocatalyzed by recoverable BINAM-prolinamide derivatives, can be highly accelerated by a catalytic amount of a carboxylic acid without compromising the obtained enantioselectivities. This application is significant for the development of chiral drugs with improved efficacy and reduced side effects.
Used in Enantioselective Catalysis:
(S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE is used as a chiral ligand in enantioselective catalysis, which is essential for producing chiral molecules with specific three-dimensional structures. This is particularly important in the synthesis of pharmaceuticals and agrochemicals, where the stereochemistry of the molecules can significantly impact their biological activity and selectivity.

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. When heated todecomposition it emits toxic fumes of NOx.

Upstream product

• 581-89-5 2-nitronaphthalene 
• 76905-82-3 2,2'-dinitro-[1,1']binaphthyl 
• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 2243-57-4 2-hydrazinonaphthalene 
• 613-64-9 1,2-di(naphthalen-2-yl)hydrazine 
• 71-43-2 benzene 
• 582-08-1 2,2'-azonaphthalene 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 21597-54-6 Methyl 3-amino-2-naphthoate 
• 188-55-6 benzo[f]naphtho[2,1-c]cinnoline 
• 64-19-7 acetic acid 
• 7803-57-8 hydrazine hydrate 
• 100-63-0 phenylhydrazine 

Downstream Products

• 194-59-2 7H-dibenzo[c,g]carbazole 
• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 18741-86-1 N,N'-(1,1'-binaphthyl-2,2'-diyl)dibenzamide 
• 76905-80-1 (S)-2,2'-diiodo-1,1'-binaphthyl 
• 10147-27-0 4,5-diphenyl-dinaphtho[2,1-e;1',2'-g][1,4]diazocine 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 
• 18531-95-8 (S)-2,2'-diamino-1,1'-binaphthalene 
• 93621-65-9 2,2'-bis(acetamido)-1,1'-binaphthyl 
• 194718-21-3 2,2′-bis-(isothiocyanato)binaphthyl 
• 847174-15-6 (S)-2,2'-bis(3-pyridylcarbonylamino)-1,1'-binaphthyl 

Relevant academic research and scientific papers

Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene

The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.

AROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICE USING THE SAME

The present invention relates to an organic electronic device wherein an organic substance layer has a novel compound which improves the service life, efficiency, driving voltage reduction, and stability of the organic electronic device. More specifically, in the present invention, the organic electronic device is an electrode using holes and/or electrons and a device which needs the exchange of electric charges between organic substances. The organic electronic device is divided largely into two devices by an operation principle.

Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes

A catalytic, enantioselective, Lewis base-catalyzed α-sulfenylation of silyl enol ethers has been developed. To avoid acidic hydrolysis of the silyl enol ether substrates, a sulfenylating agent that did not require additional Br?nsted acid activation, namely N-phenylthiosaccharin, was developed. Three classes of Lewis bases - tertiary amines, sulfides, and selenophosphoramides - were identified as active catalysts for the α-sulfenylation reaction. Among a wide variety of chiral Lewis bases in all three classes, only chiral selenophosphoramides afforded α-phenylthio ketones in generally high yield and with good enantioselectivity. The selectivity of the reaction does not depend on the size of the silyl group but is highly sensitive to the double bond geometry and the bulk of the substituents on the double bond. The most selective substrates are those containing a geminal bulky substituent on the enoxysilane. Computational analysis revealed that the enantioselectivity arises from an intriguing interplay among sterically guided approach, distortion energy, and orbital interactions.

Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) via C-C bond cleavage and nitrogen migration: A versatile synthesis of U-shaped azaacenes

An oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) that involves the cleavage of a strong C-C single bond of the binaphthalene unit and the nitrogen migration has been discovered. The unprecedented rearrangement enables access to a series of U-shaped azaacenes otherwise difficult to prepare in a selective manner by classical methods. Moreover, physicochemical properties of the unique azaacenes have been comprehensively investigated. This journal is the Partner Organisations 2014.

CuCl2 and FeCl3 as a new and efficient catalyst for the oxidative coupling of aryl amines into 1,1′-binaphthalene-2,2 /-diamines in the ionic liquid media

A practical synthesis of 1,1′-binaphthalene-1,1′-diamines (BINAM) from a-naphthylamine is described here. The facile purification procedure of the method makes it amenable to gram scale synthesis of 1,1′-binaphthalene-1,1′-diamines with fairly high optical purity and yield of product.

Iron(III)-promoted oxidative coupling of naphthylamines: Synthetic and mechanistic investigations

A facile route to the synthesis of 1,1′-binaphthyl-4,4′- diamines (naphthidines) and 1,1′-binaphthyl-2,2′-diamines (BINAMs) was developed by the oxidative homocoupling of 1- and 2-naphthylamines, respectively, using FeCl3 as oxidant and K2CO3 as base in 1,2-dichloroethane under ambient conditions. A preliminary mechanistic investigation was performed by the ESR spectroscopy and intermediate-trapping technique.

A simple and neutral receptor acting as a sensitive and switch-on fluorescent chemosensor for H2PO4-

A novel artificial anion chemosensor 1 based on 2, 2'-di (4-nitrophenylurea-β-N-yl) -1, 1'-binaphthyl is designed and synthesized for sensing anions including halide ions and oxoanions. The fluorescent emission of the binaphthyl of receptor 1, forming the hydrogen bonding with anions as the sensing mechanism, is monitored in DMSO for detecting anions. In brief, while most of the anion chemosensors are switch-off fluorescent chemosensor, or non-fluorescent sensor, receptor 1 exhibits obviously the switch-on emission during the complexation with H2PO4-. Springer Science+Business Media, LLC 2009.

Acid-catalyzed [3,3] sigmatropic rearrangement of N-Cbz-diaryl hydrazide for the synthesis of mono-N-Cbz-1,1′-biaryl-2,2′-diamine

N-Cbz-Diaryl hydrazides undergo acid-catalyzed [3,3] sigmatropic rearrangement to afford N-Cbz-1,1′-biaryl-2,2′-diamines. The resultant products can be versatile synthetic platforms for a wide variety of C2- and/or nonsymmetric axially chiral ligands and organocatalysts. N-Cbz-Diaryl hydrazides bearing either a neutral or electron-donating group underwent highly efficient acid-catalyzed [3,3] sigmatropic rearrangement to afford N-Cbz-1,1′-biaryl-2,2′-diamines. The resultant products allow elaboration of various new C2- and/or nonsymmetric axially chiral ligands or organocatalysts.

M-CPBA/TFA: An efficient nonmetallic reagent for oxidative coupling of 1,2-diarylethylenes

A mild synthesis of a series of phenanthrenes with different substituents on the phenanthrene ring is described. The method involves intramolecular oxidative coupling of a variety of 1,2-diarylethylene derivatives in the presence of m-chloroperoxybenzoic acid (m-CPBA) in trifluoroacetic acid (TFA) to yield phenanthrenes in high yields. The present approach solves a key step for the synthesis of polycyclic structures related to an alkaloid tylophorine.

A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide

Oxidative intramolecular coupling of the aryl rings of various stilbenes for direct construction of the phenanthrene ring system is promoted efficiently by manganese dioxide-trifluoroacetic acid at room temperature in excellent yields. This approach is also applied to the intermolecular biaryl coupling of 2-naphthols, 2-naphthalenethiol, 2-naphthylamine, a phenol ether and a phenol under very mild conditions. An electron-transfer mechanism is proposed in which manganese dioxide acts as a two-electron oxidant.