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

Chemical Properties

white crystalline.

Uses

2,4-Dimethyldiphenylamine is mainly used in organic synthesis and pharmaceutical intermediates.

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 
• 95-68-1 2,4-Xylidine 
• 98-11-3 benzenesulfonic acid 
• 591-50-4 iodobenzene 
• 89-87-2 2,4-dimethylnitrobenzene 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 62-53-3 aniline 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 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

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.

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.