10546-24-4

Usage

Safety Profile

Suspected carcinogen with experimental carcinogenic and tumorigenic data. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C11H11N/c1-8-6-9-4-2-3-5-10(9)7-11(8)12/h2-7H,12H2,1H3

Upstream product

• 1204-72-4 2-Methyl-3-nitronaphthalene 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 30159-70-7 3-hydroxymethyl-2-naphthol 
• 1589038-47-0 tert-butyl (3-methylnaphthalen-2-yl)carbamate 
• 39110-32-2 3-hydroxynaphthalene-2-carboxylic acid 
• 91-57-6 2-Methylnaphthalene 
• 2969-53-1 3-methyl-5,6,7,8-tetrahydronaphthalen-2-ol 
• 5959-52-4 2-Amino-3-naphthoic acid 
• 17324-04-8 3-methyl-naphthalen-2-ol 

Downstream Products

• 1204-72-4 2-Methyl-3-nitronaphthalene 
• 857488-49-4 N-(3-methyl-[2]naphthyl)-benzamide 
• 174141-05-0 3-Methylnaphthalin-2-carbonitril 
• 91-57-6 2-Methylnaphthalene 

Relevant academic research and scientific papers

Asymmetric Activation/Deactivation of Racemic Ru Catalysts for Highly Enantioselective Hydrogenation Irrespective of Ketonic Substrates: Molecular Design of Dimethylbinaphthylamine for Enantiomeric Catalysts Discrimination

Asymmetric activation and deactivation of racemic catalysts are two extremes in asymmetric catalysis. In a combination of these two protocols, higher enantioselectivity can be achieved by maximizing the difference in catalytic activity between the enantiomers of racemic catalysts through selective activation and deactivation of enantiomeric catalysts. 3,3′-Dimethyl-2,2′-diamino-1,1′-binaphthyl (DM-DABN) is thus designed as a chiral poison (deactivator) for complete enantiomer resolution of racemic BINAP-Ru(II) catalysts. The catalyst system of DM-DABN, 1,2-diphenylethylenediamine (DPEN), and racemic BINAP-Ru(II) led to great success in highly enantioselective hydrogenation irrespective of the ketonic substrates. The lower catalytic activity of the BINAP-Ru(II)/DM-DABN complex stems from the electron delocalization from the Ru center to the diamine moiety in contrast to the BINAP-Ru(II)/DPEN complex where the highest electron densities are localized on the Ru-N region. The present 'asymmetric activation/deactivation protocol' can provide a guiding principle for the rational design of a molecule for enantiomeric discrimination between racemic catalysts.

Asymmetric catalysis of homo-coupling of 3-substituted naphthylamine and hetero-coupling with 3-substituted naphthol leading to 3,3′-dimethyl-2, 2′-diaminobinaphthyl and -2-amino-2′-hydroxybinaphthyl

Optically active 3,3′-dimethyl-2,2′-diamino-1,1′- binaphthyl (DM-DABN) and 3,3′-dimethyl-2-amino-2′-hydroxybinaphthyl (DM-NOBIN) derivatives were synthesized by Cu-(-)-sparteine complex-catalyzed enantioselective homo- and hetero-coupling of 2-naphthylami

Phenyl substituted fused tricyclic compound and uses thereof

The present invention relates to a phenyl substituted fused tricyclic compound and uses thereof, further to a pharmaceutical composition containing the compound. According to the present invention, the compound or the pharmaceutical composition can be use

Nickel-catalyzed reductive and borylative cleavage of aromatic carbon-nitrogen bonds in N-aryl amides and carbamates

The nickel-catalyzed reaction of N-aryl amides with hydroborane or diboron reagents resulted in the formation of the corresponding reduction or borylation products, respectively. Mechanistic studies revealed that these reactions proceeded via the activation of the C(aryl)-N bonds of simple, electronically neutral substrates and did not require the presence of an ortho directing group.

Organocatalytic aryl-aryl bond formation: An atroposelective [3,3]-rearrangement approach to BINAM derivatives

Herein we disclose an organocatalytic aryl-aryl bond-forming process for the regio- and atroposelective synthesis of 2,2′-diamino-1,1′- binaphthalenes (BINAMs). In the presence of catalytic amounts of axially chiral phosphoric acids, achiral N,N′-binaphthyl hydrazines undergo a facile [3,3]-sigmatropic rearrangement to afford enantiomerically enriched BINAM derivatives in good to excellent yield. This transformation represents the first example of a metal-free, catalytic C(sp2)-C(sp2) bond formation between two aromatic rings with concomitant de novo atroposelective installation of an axis of chirality. Density functional calculations reveal that, in the transition state for C-C bond formation, the phosphoric acid proton of the catalyst is fully transferred to one of the N-atoms of the substrate, and the resulting phosphate acts as a chiral counterion.

Process for producing an optically active ruthenium-phosphine complex and process for producing an optically active alcohol by using the complex

Provided is a process for preparing an optically active ruthenium-phosphine complex represented by the following formula (1): wherein L represents a bidentate ligand compound of a tertiary phosphine; X represents a halogen atom; and * means chiral center (L* is an optically active substance), which comprises reacting a ruthenium-phosphine complex represented by: RumXnLpAq or [RuX(D)(L)]X wherein, X and L have the same meanings as described above (L is a racemic modification); A represents triethylamine (Et3N), etc.; and m, n, p and q each stands for an integer and D represents benzene, etc. with ? equivalent of a specific optically active chiral diamine, thereby inactivating one of the enantiomers; and then with a specific optically active diamine derivative, thereby activating the other enantiomer.

Chemical process

Aromatic amines (e.g., aniline) are selectively alkylated in an ortho nuclear position by reaction with an olefin (e.g., ethylene) in the presence of an aluminum anilide catalyst. Hydrogen halides (e.g., HCl) are added to increase the reaction rate.