634-43-5

Basic information

• Product Name: 1-(P-TOLUIDINO)NAPHTHALENE
• Synonyms: N-(P-TOLYL)-1-NAPHTHYLAMINE;1-(P-TOLUIDINO)NAPHTHALENE;N-p-tolylnaphthalen-1-amine;1-Naphthalenamine, N- (4-methylphenyl)-;(4-methylphenyl)-(1-naphthyl)amine;N-(4-methylphenyl)naphthalen-1-amine;N-4-Tolyl-1-naphthylamine;NSC 37610
• CAS NO: 634-43-5
• Molecular Formula: C₁₇H₁₅N
• Molecular Weight: 233.31
• Mol File: 634-43-5.mol

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 360 °C / 528mmHg
• Flash Point: 201.6 °C
• Appearance: /
• Density: 1.0782 (rough estimate)
• Vapor Pressure: 3.14E-06mmHg at 25°C
• Refractive Index: 1.5515 (estimate)
• Solubility: soluble in Methanol
• PKA: 1.33±0.30(Predicted)
• CAS DataBase Reference: 1-(P-TOLUIDINO)NAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(P-TOLUIDINO)NAPHTHALENE(634-43-5)
• EPA Substance Registry System: 1-(P-TOLUIDINO)NAPHTHALENE(634-43-5)

Safety Data

• Hazardous Substances Data: 634-43-5(Hazardous Substances Data)

Usage

Uses

N-(p-Tolyl)-1-naphthylamine (cas# 634-43-5) is a compound useful in organic synthesis.

InChI:InChI=1/C17H15N/c1-13-9-11-15(12-10-13)18-17-8-4-6-14-5-2-3-7-16(14)17/h2-12,18H,1H3

Upstream product

• 7664-93-9 sulfuric acid 
• 106-49-0 p-toluidine 
• 90-13-1 1-Chloronaphthalene 
• 13922-41-3 1-Naphthylboronic acid 
• 10075-72-6 1-(methylthio)naphthalene 
• 86-53-3 1-Cyanonaphthalene 
• 86-57-7 1-Nitronaphthalene 
• 5720-05-8 4-methylphenylboronic acid 
• 134-32-7 1-amino-naphthalene 
• 78-32-0 tri-p-cresyl phosphate 
• 585526-04-1 N-(4-methoxy-4-methylcyclohexa-2,5-dien-1-ylidene)-4-methylbenzenesulfonamide 
• 599-86-0 4-methyl-N-(4-methylphenyl)benzenesulfonamide 
• 90-11-9 1-Bromonaphthalene 
• 68211-49-4 1-naphthyl tosylate 

Downstream Products

• 59520-68-2 [1]naphthyl-p-tolyl-vinyl-amine 
• 19670-55-4 (9-dimethylamino-benzo[a]phenoxazin-5-ylidene)-p-tolyl-amine 
• 192461-90-8 (rac)-N-p-tolyl-1,2,3,4-tetrahydronaphthalen-1-amine 
• 174081-58-4 N,N′-bis(4-tolyl)-1,1′-binaphthalene-4,4′-diamine 
• 63039-89-4 7-ethyl-9-methyl-benz[c]acridine 
• 13493-36-2 7-Chlor-9-methyl-7,12-dihydro-benzophenarsazin 

Relevant articles and documents

Nickel-Catalyzed Amination of Aryl Nitriles for Accessing Diarylamines through C?CN Bond Activation

A nickel-catalyzed amination to access diarylamines has been developed through C?CN bond activation of aryl nitriles with anilines. In this developed catalytic protocol, various aromatic and heteroaromatic nitriles could be utilized as the electrophiles to couple with substituted anilines. A diversity of diarylamines were obtained in 15–95% yields. (Figure presented.).

Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling

Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines

The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.

Palladium-catalyzed c(sp2)-n bond cross-coupling with triaryl phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(?-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Insights on bimetallic micellar nanocatalysis for buchwald-hartwig aminations

A nanocatalyst for micellar Buchwald-Hartwig aminations is developed, thoroughly characterized, and applied on a variety of substrates. The catalyst is stable under ambient conditions for at least six months. The catalyst retained its activity after several cycles, and its structure remained intact as confirmed by NMR spectroscopy. Association of Pd nanoparticles with Cu by a phosphine ligand is revealed by 31P NMR spectroscopy, and their linkage with the activated carbon surface is revealed by XAS analysis. Control NMR experiments revealed the binding of the ligand with both Cu and Pd, and all phosphine molecules are under the same environment. In addition to NMR and XAS analysis, the catalyst is characterized by SEM, HRTEM, XPS, and TGA. Reactions are highly reproducible at variable scales. Environmentally benign, proline-based amphiphile PS-750-M is critical for catalytic activity, which is achieved under mild conditions in water as the reaction medium. The inherent sustainability of these conditions coupled with a low E factor achievable through robust recycling of catalyst and reaction medium demonstrates the significant utility of this technology.

Method for synthesizing diarylamine by optical/nickel concerted catalysis

The invention discloses a method for synthesizing diarylamine by optical/nickel concerted catalysis. According to the method, a ligand does not need to be added, and simple and cheap nickel salt is directly used as a metal catalyst to cooperate with a photosensitizer to catalyze arylamine and aryl bromide to generate cross-coupling. The method has the following advantages: (1) the use amount of BODIPY type organic photocatalyst is low, and the BODIPY type organic photocatalyst has a better catalysis effect in comparison with metal iridium and ruthenium photocatalysts reported in the literature; (2) the BODIPY type organic photocatalyst is easy for synthesis; (3) the use amount of nickel salt is few, and the ligand does not need to be added; and (4) the reaction conditions are mild, and theyield of most coupling products is higher than 90%. According to the method disclosed by the invention, high temperature and high pressure equipment is not needed, temperature change scope is small,experimental procedure is simple and easy to operate, and the method has a relatively high application value and industrial popularization potential.

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