1183962-77-7

Basic information

• Product Name: 4-methyl-2-(naphthalen-1-yl)aniline
• Synonyms: 4-methyl-2-(naphthalen-1-yl)aniline
• CAS NO: 1183962-77-7
• Molecular Weight: 233.313
• Mol File: 1183962-77-7.mol

Chemical Properties

• CAS DataBase Reference: 4-methyl-2-(naphthalen-1-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-2-(naphthalen-1-yl)aniline(1183962-77-7)
• EPA Substance Registry System: 4-methyl-2-(naphthalen-1-yl)aniline(1183962-77-7)

Safety Data

• Hazardous Substances Data: 1183962-77-7(Hazardous Substances Data)

Upstream product

• 583-68-6 2-bromo-p-toluidine 
• 13922-41-3 1-Naphthylboronic acid 

Downstream Products

• 1426812-93-2 4-methyl-N-(4-methyl-2-(naphthalen-1-yl)phenyl)benzenesulfonamide 
• 1232133-56-0 C₁₉H₁₇NO 
• 1426813-16-2 2-methyl-5-tosylbenzo[k]phenanthridin-6(5H)-one 

Relevant articles and documents

Palladium(II)-catalyzed mono-and bis-alkenylation of N-acetyl-2-aminobiaryls through regioselective C-H bond activation

We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C-H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono-and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety of functional groups to unactivated olefins.

Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via base-promoted homolytic aromatic substitution

A transition-metal-free phenanthrene synthesis starting from readily accessible ortho-amino-biaryls is presented. The biarylamines are in situ transformed into the corresponding diazonium salts which upon single electron reduction give the corresponding a

Synthesis of Axially Chiral Biaryl-2-amines by PdII-Catalyzed Free-Amine-Directed Atroposelective C?H Olefination

A simple and ubiquitously present group, free amine, is used as a directing group to synthesize axially chiral biaryl compounds by PdII-catalyzed atroposelective C?H olefination. A broad range of axially chiral biaryl-2-amines can be obtained in good yields with high enantioselectivities (up to 97 % ee). Chiral spiro phosphoric acid (SPA) proved to be an efficient ligand and the loading could be reduced to 1 mol % without erosion of enantiocontrol in gram-scale synthesis. The resulting axially chiral biaryl-2-amines also provide a platform for the synthesis of a set of chiral ligands.

Palladium-Catalyzed Benzofulvenation of o-Arylanilines through C?H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene

We report the first example of Pd(II)-catalyzed highly step- and atom-economical benzofulvenation through free amine-directed ortho C?H bond activation of o-arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o-arylaniline substrates through C?H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics. (Figure presented.).

Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.

Palladium-Catalyzed C-H Bond Activation by Using Iminoquinone as a Directing Group and an Internal Oxidant or a Co-oxidant: Production of Dihydrophenanthridines, Phenanthridines, and Carbazoles

A palladium-catalyzed C-H bond activation reaction, via a redox-neutral pathway, for the preparation of dihydrophenanthridine, phenanthridine, and carbazole derivatives from biaryl 2-iminoquinones is developed. The preinstalled iminoquinone was designed to act as a directing group for ortho C-H activation and an internal oxidant or a co-oxidant. This catalysis proceeded through the following sequence: C-H bond activation, coordination and insertion of activated olefins, β-hydride elimination, H-shift, insertion, and protonation or β-hydride elimination. In addition, carbazoles can be prepared efficiently by using this method without the addition of external oxidants.

Palladium-Catalyzed Selective Aryl Ring C–H Activation of N-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes

Palladium-catalyzed cycloaromatization of N-acyl-2-aminobiaryls, through a sequence of ortho C?H bond activation/alkyne insertion/meta C?H bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl-substituted naphthalenes, N-[2-(5,6,7,8-tetraarylnaphthalen-1-yl)aryl]acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic protocol, two compounds were converted into corresponding fluorescent carbazoles in 30–40% yield by intramolecular C?N bond formation. (Figure presented.).

Metal-free synthesis of 6-phosphorylated phenanthridines: Synthetic and mechanistic insights

A novel and efficient method for the generation of phosphinoyl radicals from the combination of diphenyliodonium salt (Ph2I+,-OTf) with triethylamine (Et3N) in the presence of secondary phosphine oxides is reported. By employing this practical and simple approach, a large variety of 6-phosphorylated phenanthridines have been synthesized through the addition of phosphinoyl radicals to isonitriles as radical acceptors. The reaction works smoothly in the absence of any transition metal or photocatalyst. On the basis of electron paramagnetic resonance (EPR) and density functional theory (DFT) calculations, the mechanism of this reaction is discussed.

Palladium-catalyzed oxidative insertion of carbon monoxide to N -sulfonyl-2-aminobiaryls through C-H bond activation: Access to bioactive phenanthridinone derivatives in one pot

Palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C-H bond activation and C-C, C-N bond formation under TFA-free and milder conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important phenanthridinone derivatives in yields up to 94%.

Palladium-catalyzed and hybrid acids-assisted synthesis of [60]fulleroazepines in one pot under mild conditions: Annulation of N-sulfonyl-2-aminobiaryls with [60]fullerene through sequential C-H bond activation, C-C and C-N bond formation

An extraordinarily efficient hybrid acids-assisted, palladium-catalyzed and chelating-group-assisted C-H bond activation of N-sulfonyl-2-aminobiaryls and their annulations with [60]fullerene via sequential C-C and C-N bond formation at room temperature to