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
• Article Data: 20

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

Description

2,4-Dimethyldiphenylamine is an organic compound characterized by its white crystalline appearance. It is a derivative of diphenylamine with two methyl groups attached at the 2nd and 4th positions, which contributes to its unique chemical properties and applications.

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.

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.

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.