32446-14-3

Usage

Uses

Used in Chemical Industry:
2,5-dimethyl-N-phenylaniline is used as a key intermediate in the synthesis of dyes and pigments, contributing to the coloration and stability of these products in various applications.
Used in Pharmaceutical Manufacturing:
2,5-dimethyl-N-phenylaniline serves as an intermediate in the production of pharmaceuticals, playing a crucial role in the development of new medications and therapeutic agents.
Used in Agricultural Chemical Production:
2,5-dimethyl-N-phenylaniline is utilized in the manufacturing process of agricultural chemicals, potentially contributing to the effectiveness of these products in crop protection and enhancement.
Used in Textile Industry:
Due to its properties, 2,5-dimethyl-N-phenylaniline is employed in the textile sector, particularly for dyeing and finishing processes, to achieve desired colorfastness and aesthetic qualities in fabrics.
It is important to handle 2,5-dimethyl-N-phenylaniline with care, as it may present health risks if not properly controlled and managed.

Upstream product

• 51786-47-1 N-phenyl-2,5-dimethylacetanilide 
• 1122-42-5 2-iodo-p-xylene 
• 62-53-3 aniline 
• 106-42-3 para-xylene 
• 100-65-2 N-Phenylhydroxylamine 
• 100-63-0 phenylhydrazine 
• 95-72-7 2-chloro-1,4-dimethyl-benzene 
• 95-78-3 2,5-Dimethylaniline 
• 108-90-7 chlorobenzene 
• 103-84-4 Acetanilid 
• 52512-26-2 4,5-dimethyl-N-phenyl-4-oxazolin-2-one 
• 78-94-4 methyl vinyl ketone 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines

A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.

A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters

A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used. Wiley-VCH Verlag GmbH & Co. KGaA.

A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides

A new class of one-component Pd precatalysts bearing biarylphosphine ligands is described. These precatalysts are air- and thermally stable, are easily activated under normal reaction conditions at or below room temperature, and ensure the formation of the highly active monoligated Pd(0) complex necessary for oxidative addition. The use of these precatalysts as a convenient source of LPd(0) in C-N cross-coupling reactions is explored. The reactivity that is demonstrated in this study is unprecedented in palladium chemistry. Copyright

Water-mediated catalyst preactivation: An efficient protocol for C-N cross-coupling reactions

(Figure Presented) A protocol for forming a highly active Pd(O) catalyst from Pd(OAc)2, water, and biaryldialkylphosphine ligands has been developed. This protocol generates a catalyst system, which exhibits excellent reactivity and efficiency in the coupling of a variety of amides and anilines with aryl chlorides.

Carbene adduct of cyclopalladated ferrocenylimine as an efficient catalyst for the amination of aryl chlorides

A novel air- and moisture-stable carbene adduct of cyclopalladated ferrocenylimine has been synthesized and characterized. The structure of this compound was determined by X-ray crystal structure analysis. This adduct has been applied as an efficient catalyst for the amination of aryl chlorides.

Amination of aryl chlorides in water catalyzed by cyclopalladated ferrocenylimine complexes with commercially available monophosphinobiaryl ligands

The easily accessible, air- and moisture-stable cyclopalladated ferrocenylimine complex 3 was found to be a highly active one-component precatalyst for the amination of aryl chlorides in water in the presence of inexpensive KOH and t-BuOH as a base and an additive, respectively.

Triazole-based monophosphine ligands for palladium-catalyzed cross-coupling reactions of aryl chlorides

A variety of triazole-based monophosphines (ClickPhos) have been prepared via efficient 1,3-dipolar cycloaddition of readily available azides and acetylenes. Their palladium complexes provided excellent yields in the amination reactions and Suzuki-Miyaura coupling reactions of unactivated aryl chlorides. Ligand 7i, which has a 2,6-dimethoxybenzene moiety, provided good results in Suzuki-Miyaura reaction to form hindered biaryls. A CAChe model for the Pd/7i complex shows that the likelihood of a Pd-arene interaction might be a rationale for its high catalytic reactivity.

CLICKPHOSPHINES FOR TRANSITION METAL-CATALYZED REACTIONS

Phosphine triazole ligand compounds, prepared through click chemistry, complex with transition metals to form transition metal-phosphine triazole ligand complexes. These complexes are useful catalysts in coupling reactions such as Suzuki-Miyaura coupling, Stille coupling, Negishi coupling, Sonagashira coupling, carbon-heteroatom bond-forming reactions (C-O and C-N), alpha alkylation of carbonyls, Heck coupling reactions, and hydrogenation reactions.

Reaction of phenylhydrazines with arenes in the presence of aluminium trichloride

Phenylnitrenium ions are generated from phenylhydrazines by treatment with AlCl3. Reaction of a phenylnitrenium ion with arenes results in both aromatic N-substitution and C-substitution. In contrast, an N-methylphenylnitrenium ion undergoes exclusively aromatic C-substitution. Reaction of a phenylnitrenium ion with arenes present only in slight excess produces anilinated products in moderate to good yields.

N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride

A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.