29601-75-0

Basic information

• Product Name: 2-Amino-1-phenylnaphthalene
• Synonyms: 2-Amino-1-phenylnaphthalene
• CAS NO: 29601-75-0
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.28112
• Mol File: 29601-75-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Amino-1-phenylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-1-phenylnaphthalene(29601-75-0)
• EPA Substance Registry System: 2-Amino-1-phenylnaphthalene(29601-75-0)

Safety Data

• Hazardous Substances Data: 29601-75-0(Hazardous Substances Data)

Usage

Chemical compound

2-Amino-1-phenylnaphthalene

Type of compound

Polycyclic aromatic hydrocarbon

Uses

Building block in the synthesis of organic compounds, precursor in the production of dyes, pigments, and pharmaceuticals

Structure

Contains a naphthalene ring with an attached amino group and a phenyl group

Potential applications

Organic electronics and materials science

Upstream product

• 581-89-5 2-nitronaphthalene 
• 71-43-2 benzene 
• 624-38-4 para-diiodobenzene 
• 91-59-8 naphthalen-2-ylamine 
• 589-87-7 1,4-bromoiodobenzene 
• 93-09-4 naphthalene-2-carboxylate 
• 90016-93-6 2-Amino-1-iodonaphthalene 
• 98-80-6 phenylboronic acid 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 462-06-6 fluorobenzene 
• 20191-75-7 1-bromo-2-naphthylamine 
• 607-23-8 2-nitro-1-naphthylamine 
• 94256-73-2 N-<1-Phenyl-naphth-2-yl>-carbaminsaeure-aethylester 

Downstream Products

• 1283747-47-6 7-(phenylsulfonyl)-7H-benzo[c]carbazole 
• 1283747-12-5 2-benzenesulfonylamido-1-phenylnaphthalene 
• 109812-54-6 N-(1-phenyl-[2]naphthyl)-acetamide 
• 195-29-9 Benzophenanthridin 

Relevant articles and documents

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.

"transition-metal-free" synthesis of carbazoles by photostimulated reactions of 2′-halo[1,1′-biphenyl]-2-amines

An efficient and simple protocol for the preparation of a series of 9H-carbazoles by photostimulated SRN1 substitution reactions is presented. Substituted 9H-carbazoles were synthesized in low to excellent yields (up to 96%) through an intramolecular C-N bond formation of 2′-halo[1,1′-biphenyl]-2-amines by the photoinitiated SRN1 mechanism under mild and "transition-metal-free" conditions. The biphenylamines used as substrates were obtained with isolated yields ranging from 21% to 84% by two approaches: (A) the cross-coupling Suzuki-Miyaura reaction and (B) the radical arylation of anilines. Some key aspects of the proposed mechanism were evaluated at the B3LYP/6-311+G? level.

Direct intermolecular aniline ortho- arylation via benzyne intermediates

A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.