25078-04-0

Basic information

• Product Name: 2,4-Dimethyldiphenylamine
• Synonyms: 2,4-DIMETHYLDIPHENYLAMINE;PHENYL(2,4-XYLYL)AMINE;N-PHENYL-2,4-XYLIDINE;TRIS(4-BROMOPHENYL)2,4-DIMETHYL DIPHENYLAMINE;2,4-DiMethyl-N-phenylbenzenaMine;N-Phenyl-2,4-xylidine Phenyl(2,4-xylyl)amine;2,4-DiMethyl-N-phenylaniline
• CAS NO: 25078-04-0
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.28
• EINECS: 1533716-785-6
• Mol File: 25078-04-0.mol

Chemical Properties

• Melting Point: 43°C
• Boiling Point: 170°C 3mm
• Flash Point: 0°C
• Appearance: /
• Density: 1.049g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 1.11±0.40(Predicted)
• CAS DataBase Reference: 2,4-Dimethyldiphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethyldiphenylamine(25078-04-0)
• EPA Substance Registry System: 2,4-Dimethyldiphenylamine(25078-04-0)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 25078-04-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4-Dimethyldiphenylamine is used as a key intermediate in the synthesis of various organic compounds. Its chemical structure allows for a range of reactions, making it a versatile building block in the creation of different molecules.
Used in Pharmaceutical Intermediates:
In the pharmaceutical industry, 2,4-Dimethyldiphenylamine serves as an essential intermediate for the development of various drugs. Its unique properties enable the formation of new drug candidates with potential therapeutic applications.
Overall, 2,4-Dimethyldiphenylamine is a valuable compound in both the organic synthesis and pharmaceutical sectors, playing a crucial role in the development of new molecules and drug candidates.

InChI:InChI=1/C14H15N/c1-11-8-9-14(12(2)10-11)15-13-6-4-3-5-7-13/h3-10,15H,1-2H3

Synthetic route

bromobenzene (108-86-1) + 2,4-Xylidine (95-68-1) → N-(2,4-dimethylphenyl)aniline (25078-04-0)

Conditions	Yield
With sodium t-butanolate at 110℃; for 18h;	98%

chlorobenzene (108-90-7) + 2,4-Xylidine (95-68-1) → N-(2,4-dimethylphenyl)aniline (25078-04-0)

Conditions	Yield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In toluene at 100℃; for 3h; Inert atmosphere;	95%
With C33H40ClN3O2Pd; potassium tert-butylate In toluene at 130℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	95%

Upstream product

• 303051-44-7 N-Acetyl-N-(2,4-dimethylphenyl)aniline 
• 108-38-3 m-xylene 
• 622-37-7 Phenyl azide 
• 142-04-1 aniline hydrochloride 
• 95-68-1 2,4-Xylidine 
• 98-11-3 benzenesulfonic acid 
• 591-50-4 iodobenzene 
• 1122-42-5 2-iodo-p-xylene 
• 103-84-4 Acetanilid 
• 108-86-1 bromobenzene 
• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 108-90-7 chlorobenzene 
• 89-87-2 2,4-dimethylnitrobenzene 
• 108-94-1 cyclohexanone 

Downstream Products

• 944330-26-1 4-(4-methyldiphenylamino)-4'-(2,4-dimethyldiphenylamino)-p-terphenyl 
• 944330-25-0 4,4'-bis(2,4-dimethyldiphenylamino)-p-terphenyl 
• 122738-25-4 N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine 
• 1131890-87-3 5-methyl-1,2-diphenyl-1H-indole 

Relevant articles and documents

Chitosan nanoparticles functionalized poly-2-hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N-arylation of amines with phenylboronic acid at ambient temperature

The present study aims to prepare an effective and eco-friendly nanocatalyst for the Chan–Lam coupling reaction of phenylboronic acid and amine in aerobic conditions. For this purpose, chitosan was extracted from shrimp shells waste by demineralization, deproteinization, and deacetylation processes and then converted to chitosan nanoparticles (CSN) by the ionic gelation with tripolyphosphate anions. Afterward, poly-2-hydroxyaniline (P2-HA) was grafted to chitosan nanoparticles (NPs) to employ as the support for CuO NPs. Characterization of the nanocatalyst was done using Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), mapping, energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The CuO NPs were identified in the spherical shape with an average size of 17 nm. The prepared nanocatalyst exhibited excellent catalytic performance with a high turnover number (TON) and turnover frequency (TOF) for the Chan–Lam coupling reaction of phenyl boronic acid and amines with different electronic properties. The prepared catalyst could be readily recovered and reused for at least five runs without any noticeable change in structure and catalytic performance. Chitosan (CS) was prepared via demineralization, deproteinization, and deacetylation of shrimp shell and chitosan nanoparticles (CSN) were prepared via ionic gelation process. Polymerization of 2-HA on the CSN surface was done to increase functional groups and create active sites for CuO NPs attachments. CuO NPs-P2-HA-CSN nanocomposite has been shown high efficiently for the Chan–Lam coupling reaction.

Reductive C?N Coupling of Nitroarenes: Heterogenization of MoO3 Catalyst by Confinement in Silica

The construction of C?N bonds with nitroaromatics and boronic acids using highly efficient and recyclable catalysts remains a challenge. In this study, nanoporous MoO3 confined in silica serves as an efficient heterogeneous catalyst for C?N cross-coupling of nitroaromatics with aryl or alkyl boronic acids to deliver N-arylamines and with desirable multiple reusability. Experimental results suggest that silica not only heterogenizes the Mo species in the confined mesoporous microenvironment but also significantly reduces the reaction induction period and regulates the chemical efficiency of the targeted product. The well-shaped MoO3@m?SiO2 catalyst exhibits improved catalytic performance both in yield and turnover number, in contrast with homogeneous Mo catalysts, commercial Pd/C, or MoO3 nanoparticles. This approach offers a new avenue for the heterogeneous catalytic synthesis of valuable bioactive molecules.

Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores

The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.

PHOTOSENSITIVE RESIN COMPOSITION, PHOTOSENSITIVE RESIN LAYER USING THE SAME AND COLOR FILTER

A photosensitive resin composition, a photosensitive resin layer, and a color filter, the composition including a colorant including a first green dye having a core-shell structure and a second green dye in a weight ratio of about 1:9 to about 7:3; a binder resin; a photopolymerizable compound; a photopolymerization initiator; and a solvent.

Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane

The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.

NOVEL COMPOUND, CORE-SHELL DYE, PHOTOSENSITIVE RESIN COMPOSITION INCLUDING THE SAME, AND COLOR FILTER

Provided are: a compound represented by chemical formula 1; a core comprising the same; a core-shell dye comprising a shell surrounding a core; a photosensitive resin composition comprising the same; and a color filter manufactured by using the photosensitive resin composition. In the chemical formula 1, each substituent is as defined in the specification. By using the compound according to an embodiment or the core-shell dye, it is possible to realize the color filter excellent in brightness and a contrast ratio.COPYRIGHT KIPO 2019

Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles

Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.

Copper-(II) Catalyzed N-Formylation and N-Acylation of Aromatic, Aliphatic, and Heterocyclic Amines and a Preventive Study in the C-N Cross Coupling of Amines with Aryl Halides

A Cu-(II) catalyzed N-formylation and N-acylation of amines with moderate to excellent yields, using N, N-dimethyl formamide (DMF) and N, N-dimethyl acetamide (DMA) as a formyl and acylating sources in the presence of 1,2,4-triazole is reported. This novel, highly efficient and simple protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines. In addition, the conditions to prevent N-formylation and N-acylation impurities in the C?N cross coupling of amines and aryl halides are described typically when DMF and DMA are used as solvents, with various catalysts, ligands, and bases.

Synthesis of N-heterocyclic carbene-Pd(II) complexes and their catalytic activity in the Buchwald-Hartwig amination of aryl chlorides

Novel N-heterocyclic carbene-palladium(II) complexes using 2-picolinic acid as the ancillary ligand have been successfully developed under mild conditions. Their catalytic activity in organic synthesis has been initially tested in the Buchwald-Hartwig amination of secondary and primary amines with aryl chlorides. Various substituents on both substrates can be tolerated, giving the desired coupling products in good to almost quantitative yields. The minimum catalyst loading can be 0.01 mol%, implying their potential application toward industrial processes.

The solid copper-mediated C-N cross-coupling of phenylboronic acids under continuous flow conditions

We have developed two general methods for the C-N cross-coupling of phenylboronic acids with amines using solid copper flow reactors, in combination with an oxidant. We have developed one method for a C-N arylation reaction which employs a solid copper coil reactor, in combination with tert-butyl peroxybenzoate, to give products in moderate isolated yields. We have also developed a general method for the C-N cross coupling of phenylboronic acids using a column packed with solid copper powder, in combination with acetic acid and TEMPO, to give products in isolated yields in excess of 75+%. We have also applied our general copper powder method to generate a library of products which highlights the utility of solid copper flow reactors for C-N cross coupling reactions, generating 16 examples in good yields. Mechanistic implications and future directions are also discussed.