4316-53-4

Basic information

• Product Name: 4-Methyltriphenylamine
• Synonyms: 4—METHYLTRIPHENYLAMINE;4-Tolyldiphenylamine;4-METHYLTRIPHENYLAMINE,98.0+%(GC);N,N-Diphenyl-p-toluidine;N-(4-Methylphenyl)diphenylamine;Diphenyl p-tolylamine;Diphenyl(4-methylphenyl)amine;Diphenyl(p-methylphenyl)amine
• CAS NO: 4316-53-4
• Molecular Formula: C₁₉H₁₇N
• Molecular Weight: 259.34
• EINECS: 1533716-785-6
• Product Categories: electronic;Acid Anhydrides, etc. (Reagents for Conducting Polymer Research);Functional Materials;Reagents for Conducting Polymer Research
• Mol File: 4316-53-4.mol

Chemical Properties

• Melting Point: 67 °C
• Boiling Point: 393.8 °C at 760 mmHg
• Flash Point: 171.8 °C
• Appearance: /
• Density: 1.095 g/cm³
• Vapor Pressure: 2.08E-06mmHg at 25°C
• Refractive Index: 1.636
• Solubility: soluble in Toluene
• PKA: -2.62±0.30(Predicted)
• CAS DataBase Reference: 4-Methyltriphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyltriphenylamine(4316-53-4)
• EPA Substance Registry System: 4-Methyltriphenylamine(4316-53-4)

Safety Data

• Hazardous Substances Data: 4316-53-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Methyltriphenylamine is used as a reactant and reagent in organic synthesis for its ability to participate in a wide range of chemical reactions. Its unique structure allows it to act as a building block for the creation of more complex organic molecules, which can be utilized in various applications across different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methyltriphenylamine is used as a reactant for the synthesis of various drug molecules. Its reactivity and structural properties make it a valuable component in the development of new medications, potentially contributing to the treatment of various diseases and health conditions.
Used in Chemical Research:
4-Methyltriphenylamine is also used in chemical research as a reagent for studying the properties and behavior of organic compounds. Its involvement in various chemical reactions provides valuable insights into the mechanisms and pathways of organic synthesis, which can be applied to the development of new materials and technologies.
Used in Material Science:
In the field of material science, 4-Methyltriphenylamine can be used as a component in the development of advanced materials with specific properties. Its incorporation into the molecular structure of these materials can lead to enhanced performance characteristics, such as improved conductivity, stability, or reactivity, depending on the desired application.

InChI:InChI=1/C19H17N/c1-16-12-14-19(15-13-16)20(17-8-4-2-5-9-17)18-10-6-3-7-11-18/h2-15H,1H3

Upstream product

• 624-31-7 4-tolyl iodide 
• 122-39-4 diphenylamine 
• 591-50-4 iodobenzene 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 106-49-0 p-toluidine 
• 106-38-7 para-bromotoluene 
• 106-43-4 para-chlorotoluene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 591-17-3 meta-bromotoluene 
• 1177-35-1 2,4,6-Tris(4-methylphenoxy)-1,3,5-triazine 
• 86-74-8 9H-carbazole 
• 108-90-7 chlorobenzene 
• 108-94-1 cyclohexanone 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 404825-34-9 N,N-di(4-iodophenyl)-4-tolylamine 
• 1233934-04-7 4-methyl-N,N-bis(4-(9-(3,4,5-trifluorophenyl)-9H-fluoren-9-yl)phenyl)aniline 
• 1233933-99-7 4-methyl-N,N-bis(4-(9-(4-fluorophenyl)-9H-fluoren-9-yl)phenyl)aniline 
• 1235971-60-4 4-methyl-N,N-bis-(4-(9-p-tolyl-9H-fluoren-9-yl)phenyl)aniline 
• 1235971-59-1 4-methyl-N,N-bis-(4-(9-(naphthalen-1-yl)-9H-fluoren-9-yl)phenyl)aniline 
• 1233934-00-3 4-methyl-N,N-bis-(4-(9-(4-tert-butylphen-yl)-9H-fluoren-9-yl)phenyl)aniline 
• 1233934-02-5 4-methyl-N,N-bis(4-(9-(4-(trifluoromethyl)-phenyl)-9H-fluoren-9-yl)phenyl)aniline 
• 100308-67-6 4,4′-dibromo-4′′-methyltriphenylamine 
• 122112-54-3 4-[(4-formylphenyl)(4-methylphenyl)amino]benzaldehyde 
• 65181-78-4 4,4'-bis(m-tolylphenylamino)biphenyl 
• 1643872-88-1 1-(2,5-dimethylthiophen-3-yl)-3-(4-(N-phenyl-N-(4-methylphenyl)amino)phenyl)prop-2-en-1-one 
• 19264-73-4 9-(4-methylphenyl)-9H-carbazole 
• 1202362-88-6 3-methyl-9-phenyl-9H-carbazole 
• 199868-62-7 C₆₃H₅₅N₃ 

Relevant articles and documents

A copper(ii) complex as an intermediate of copper(i)-catalyzed C-N cross coupling of N-phenylaniline with aryl halide by in situ ESI-MS study

Complexes [Cu(NPh2)2]-, [Cu(NPh 2)I]- and K[Cu(phen)(NPh2) (p-tolyl)] + were observed by in situ electrospray ionization mass spectrometry (ESI-MS) analysis of the copper(i)-cata

Design of Benzimidazolyl Phosphines Bearing AlterableP,OorP,N-Coordination: Synthesis, Characterization, and Insights into Their Reactivity

A new series of hemilabile benzimidazolyl phosphines is reported. Entities in this ligand family can be easily assembled and prepared on a large scale via a simple one-pot procedure. X-ray crystallographic analyses show that the Pd metal center can coordinate in different fashions, where it relies on the size of the ?PR2group. With the same ligand scaffold, the ligand having a ?PCy2moiety displays better efficiency in expediting aromatic C-C bond-coupling reactions, while the ligand associated with a ?P-t-Bu2group, in contrast, promotes C-N bond-forming reactions.

A Tetraarylpyrrole-Based Phosphine Ligand for the Palladium-Catalyzed Amination of Aryl Chlorides

A tetraarylpyrrole-based phosphine ligand L1 in combination with Pd(dba)2 provided a catalyst for the Buchwald-Hartwig amination reaction. A variety of amines were rapidly coupled with aryl chlorides at a Pd loading of 0.5 mol%. The selective monoarylation of aliphatic primary amines was achieved in the presence of 0.8 equiv. water. Comparison experiments were also conducted, which revealed that the catalytic activity of L1 is superior to representative phosphine ligands in the Pd-catalyzed C?N coupling of various amines. (Figure presented.).

DIARYL AMINE COMPOUND AND METHOD FOR PRODUCING THE SAME

The present invention relates to a process for the preparation of diaryl amine compounds. A compound represented by chemical formula 1, a compound represented by chemical formula 2, and a synthetic reagent in a solvent, the synthetic reagent being CsF, KF, 18 - crown -6, K. 2 CO3, [TBAT] The present invention relates to a process for the preparation of diaryl amine compounds comprising a material selected from the group consisting of a (tetrabutylammonium difluorotriphenylsilicate), TBAF (tetrabutylammonium fluoride) and combinations thereof. Chemical Formula 1. Chemical Formula 2. The diaryl amine compound can be synthesized under the absence of a transition metal to be used to synthesize diaryl amine compounds having various substituents.

Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions

A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.

PHOSPHINE COMPOUND, CROSSLINKED COMPOSITION, AND MANUFACTURING METHOD OF AROMATIC AMINE COMPOUND

PROBLEM TO BE SOLVED: To provide a phosphine compound capable of constituting a transition metal complex excellent in reaction speed and selectivity as a catalyst. SOLUTION: There is provided a phosphine compound represented by the formula (I). In the formula Ar represents each independently an aryl group which may be substituted, R1 represents each independently a linear, branched or cyclic alkyl group, R2 represents each independently a linear, branched or cyclic alkyl group, alkoxy group or aryl group which may be substituted, or neighboring 2 R2 are bound each other to form a ring, and n represents an integer of 0 to 4. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Transition-Metal-Free Diarylation of Isocyanates with Arynes

A facile method for the transition-metal-free diarylation of isocyanates with arynes in the presence of cesium fluoride has been developed, which affords functionalized diaryl amines in moderate to excellent yields. This reaction has good functional group tolerance and provides excellent regioselectivity by utilizing a methoxy-substituted aryne precursor.

Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates

A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.

Chitosan-Supported Ni particles: An Efficient Nanocatalyst for Direct Amination of Phenols

A practical method for the direct amination of phenols using 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient promotor for the activation of phenols in the presence of an efficient and recyclable heterogeneous catalyst prepared by immobilization of nickel particles on triazole modified chitosan is described. This heterogeneous catalyst has demonstrated a promising activity for the conversion of phenolic compounds to their corresponding amine under mild conditions. Moreover, the obtained catalyst can be reused in five consecutive runs with consistent catalytic activity.

Palladium-catalyzed Selective Amination of Aryl(haloaryl)amines with 9H-Carbazole Derivatives

Palladium-catalyzed amination of aryl(haloaryl)amines with 9H-carbazole derivatives was investigated. In the amination of (4-bromophenyl)phenylamine with 9H-carbazole by the use of Pd2(dba)3/PtBu3/NaOtBu catalyst, the main product was desired 9-[4-(phenylamino)phenyl]-9H-carbazole in 60% yield with conversion of (4-bromophenyl)phenylamine >99%, and the concomitant formation of 9-[4-[phenyl[4-(phenylamino)phenyl]amino]phenyl]-9H-carbazole (15% yield), which is the consecutive by-product, was observed. When XPhos was used instead of PtBu3, the desired product was provided in 81% yield and the consecutive by-product was suppressed to 7.7%. The yield of the desired product reached 98% by the use of tBu-XPhos. Such excellent yields of the desired product were also obtained with other 2-di-tert-butyl- or 2-di(1-adamantyl)phosphino-1,1’-biaryls. Various 9-(arylamino)aryl-9H-carbazoles could be synthesized from aryl(haloaryl)amines and 9H-carbazole derivatives in high yields by the use of tBu-XPhos. The amination of 4-bromotoluene with a mixture of diphenylamine and 9H-carbazole gave only 9-o-tolyl-9H-carbazole with tBu-XPhos, while the use of PtBu3 or XPhos afforded the mixture of 9-o-tolyl-9H-carbazole and diphenyl(o-tolyl)amine, indicating that Pd2(dba)3/tBu-XPhos/NaOtBu catalyst high selectively favors 9H-carbazole over diphenylamine as an amination substrate. (Figure presented.).