95-78-3

Basic information

• Product Name: 2,5-Dimethylaniline
• Synonyms: 2,5-dimethyl-anilin;2,5-dimethyl-benzenamin;2,5-Dimethylbenzenamine;2,5-dimethyl-Benzenamine;2,5-Dimethylbenzeneamine;2,5-Dimethylphenylamine;2-amino-1,4-dimethyl-benzen;2-Amino-1,4-xylene
• CAS NO: 95-78-3
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• EINECS: 202-451-0
• Product Categories: Intermediates;Anilines, Aromatic Amines and Nitro Compounds;Amines;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 95-78-3.mol
• Article Data: 48

Chemical Properties

• Melting Point: 11.5 °C(lit.)
• Boiling Point: 218 °C(lit.)
• Flash Point: 201 °F
• Appearance: Clear yellow to red-brown/Liquid
• Density: 0.973 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.152mmHg at 25°C
• Refractive Index: n20/D 1.559(lit.)
• Storage Temp.: Store below +30°C.
• PKA: pK1:4.53(+1) (25°C)
• Water Solubility: <0.1 g/100 mL at 18℃
• Merck: 14,10084
• BRN: 2205178
• CAS DataBase Reference: 2,5-Dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethylaniline(95-78-3)
• EPA Substance Registry System: 2,5-Dimethylaniline(95-78-3)

Safety Data

• Hazard Codes: T,N,Xn
• Statements: 23/24/25-33-51/53-48/20
• Safety Statements: 28-36/37-45-61-28A
• RIDADR: UN 1711 6.1/PG 2
• WGK Germany: 3
• RTECS: ZE9100000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 95-78-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2,5-Dimethylaniline is used as a raw material for the production of organic dyes and pigments, which are essential for coloring various materials and products.
Used in Pharmaceutical Industry:
It serves as a precursor for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Agriculture:
2,5-Dimethylaniline is used in the production of agricultural chemicals, helping to improve crop protection and yield.
Used in Rubber Industry:
2,5-Dimethylaniline is utilized in the synthesis of rubber chemicals, which are vital for enhancing the properties and performance of rubber products.
Used in Antioxidant Production:
2,5-Dimethylaniline is employed in the creation of antioxidants, which are crucial for preventing the degradation of materials and extending their lifespan.
Used in Synthesis of Nanocomposites:
2,5-Dimethylaniline has been used in the synthesis of nanocomposites, such as multi-walled carbon nanotubes embedded in poly(2,5-dimethylaniline), for potential applications in various fields.
Used in Laccase Activity Studies:
It has been utilized to study the effect of metabolites formed from 2,5-xylidine by fungi on laccase activity, providing insights into its potential applications in biotechnology.
Used in Spectroscopic Studies:
The Fourier transform infrared (FTIR) and Raman spectra of 2,5-dimethylaniline have been studied, contributing to the understanding of its molecular structure and properties.
Used in Gene Expression Research:
2,5-Dimethylaniline has been found to induce the transcription of lccIV, a gene involved in laccase production, which may have implications for biotechnological applications.

Air & Water Reactions

2,5-Dimethylaniline may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2,5-Dimethylaniline ignites on contact with fuming nitric acid . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

2,5-Dimethylaniline is combustible.

Safety Profile

Suspected carcinogen. A poison. Moderately toxic by ingestion. Quesuonable carcinogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also other xylidme entries.

Purification Methods

Convert p-xylidine to a derivative (see below) which, after recrystallisation, is decomposed with alkali to give the free base. Dry over KOH and fractionally distil. The acetyl derivative has m 142o (from H2O or toluene), and the benzoyl derivative has m 140o (from EtOH). [Beilstein 12 H 1135, 12 IV 2567.]

InChI:InChI=1/C8H11N.ClH/c1-6-3-4-7(2)8(9)5-6;/h3-5H,9H2,1-2H3;1H

Upstream product

• 109-74-0 propyl cyanide 
• 553-94-6 4-bromo-m-xylene 
• 110-59-8 pentanonitrile 
• 75-05-8 acetonitrile 
• 106-42-3 para-xylene 
• 71-23-8 propan-1-ol 
• 35774-21-1 2,5-dimethylphenyl azide 
• 7647-01-0 hydrogenchloride 
• 53877-41-1 4-(2,5-dimethyl-phenylazo)-2,5-dimethyl-aniline 
• 123-51-3 i-Amyl alcohol 
• 89-58-7 mononitro-p-xylene 
• 7732-18-5 water 
• 3096-64-8 N-(2,5-dimethylphenyl)hydroxylamine 
• 330469-49-3 phenyl-methanesulfonic acid-(2,5-dimethyl-anilide) 

Downstream Products

• 87282-11-9 N,N-dibutyl-2,5-dimethyl-aniline 
• 57206-69-6 sym N,N'-bis(2,5-xylyl)thiourea 
• 6629-44-3 N-(2,5-dimethyl-anilinomethyl)-phthalimide 
• 872266-62-1 N,N'-bis-(2,5-dimethyl-phenyl)-methylenediamine 
• 5339-30-0 bis-(4-amino-2,5-dimethyl-phenyl)-methane 
• 80793-39-1 (4-amino-2,5-dimethyl-phenyl)-(4-amino-phenyl)-diazene 
• 61808-03-5 (2,5-Dimethylphenyl)-ethyl-ether 
• 860747-82-6 bis-(4-amino-2,5-dimethyl-phenyl)-(3-nitro-phenyl)-methane 
• 112523-36-1 N-(p-nitrobenzylidene)-2,5-xylidine 
• 6311-53-1 1-(2,5-dimethylphenyl)-3-phenylthiourea 
• 5177-35-5 2-chloro-N-(2,5-dimethylphenyl)acetamide 
• 132593-60-3 3-benzyl-5,8-dimethyl-quinoline-2,4-diol 
• 60453-85-2 N-(2,5-dimethylphenyl)-3-hydroxynaphthalene-2-carboxamide 
• 91181-09-8 N-(2,5-dimethyl-phenyl)-malonamide 

Relevant articles and documents

Single-atom Fe-N4site for the hydrogenation of nitrobenzene: theoretical and experimental studies

The hydrogenation of nitrobenzene to aniline is an important process in the industry of fine chemicals, but developing inexpensive catalysts with expected activity and selectivity still remains a challenge. By using density functional theory calculations, we demonstrated that the isolated Fe atom not only can weaken the adsorption of reactants and reaction intermediates as compared to Fe nanoparticles, but also remarkably decrease the reaction barrier for the hydrogenation of nitrobenzene to aniline. Thus, the Fe single-atom (Fe SA) catalyst is considered as an ideal catalyst for this reaction. This theoretical prediction has been subsequently confirmed by experimental results obtained for the Fe SAs loaded on N-doped hollow carbon spheres (Fe SAs/NHCSs) which achieved a conversion of 99% with a selectivity of 99% for the hydrogenation of nitrobenzene. The results significantly outperformed the Fe nanoparticles for this reaction. This work provides theoretical insight for the rational design of new catalytic systems with excellent catalytic properties.

C-H Amination of Arenes with Hydroxylamine

This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.

Superfine CoNi alloy embedded in Al2O3 nanosheets for efficient tandem catalytic reduction of nitroaromatic compounds by ammonia borane

Aromatic amino compounds are important and universally used chemical intermediates in a wide range of industrial fields. Thus, their production with high efficiency and selectivity under ambient conditions is expected and demanded in modern industry. Herein, a series of superfine CoNi alloy nanoparticles embedded in Al2O3 nanosheet (CoxNi1-x/Al2O3, where x represents the content of Co in the precursor) catalysts was fabricated from CoNiAl-LDH and used to catalyze the tandem dehydrogenation of ammonia borane (AB) and hydrogenation of nitroaromatics to the corresponding amines. Systematic experiments indicate that the composition, size, morphology and catalytic performance of the CoxNi1-x/Al2O3 catalysts can be easily controlled by changing the content of Ni in the CoNiAl-LDH precursor. Particularly, Co0.67Ni0.33/Al2O3 exhibited the best tandem catalytic performance among the six samples. This as-prepared catalyst not only showed a moderate turn-over-frequency value (TOF: 34.5 molH2 molCo0.67Ni0.33-1 min-1 at 298 K without base or additives) and relatively low activation energy (32.4 kJ mol-1) for the dehydrogenation of AB, but also superior catalytic activity (conversion yield reaching up to 100%) and selectivity (>99%) for the tandem reductive transformation of in excess of sixteen types of nitroaromatics to aromatic amines. Density functional theory (DFT) calculations suggest that the construction of the CoNi alloy optimized the electronic structure with respect to the pure component, promoting its activity for AB hydrolysis and nitroaromatics hydrogenation. Finally, the catalyst could be easily recycled using a magnet due to the magnetic properties of the Co0.67Ni0.33 alloy.

Pyridyl Radical Cation for C?H Amination of Arenes

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp2)?H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N?X pyridinium reagents mediated by visible light.

Solvent-Driven Selectivity Control to Either Anilines or Dicyclohexylamines in Hydrogenation of Nitroarenes over a Bifunctional Pd/MIL-101 Catalyst

The hydrogenation of nitroarenes is one of the most important strategies to produce the corresponding anilines and dicyclohexylamines, both of which are the fundamental raw materials in the synthesis of various pharmaceuticals and fine chemicals. Nevertheless, it is still a great challenge to develop a highly versatile and flexible catalytic system to selectively generate desired amines. Herein, we report the solvent-driven selectivity control over a bifunctional Pd/MIL-101 catalyst for the hydrogenation of nitrobenzene. An almost full selectivity of 99.9% to aniline or a surprising selectivity of 99.1% to dicyclohexylamine is achieved by using dimethylformamide (DMF, a polar solvent) or n-hexane (an apolar solvent) as the solvents, respectively. It is proposed that the polarity of solvents can effectively regulate the linkage between reactants/intermediates and Pd/MIL-101, affording controllable selectivities of aniline or dicyclohexylamine at will. In addition, the Lewis acid sites in Pd/MIL-101 can also effectively activate the aromatic ring and accelerate the cross-coupling reaction of amine. This solvent-driven catalytic system also exhibits good recyclability and compatibility for a wide substrate scope in both DMF and n-hexane, showing great promise for industrial applications. This study might open an avenue for the hydrogenation of nitroarenes to selectively produce anilines or dicyclohexylamines by simply regulating the solvent polarity over a bifunctional catalyst system.

Intrinsic Hydrophobicity versus Intraguest Interactions in Hydrophobically Driven Molecular Recognition in Water

Molecular recognition of water-soluble molecules is challenging but can be achieved if the receptor possesses a hydrophobic binding interface complementary to the guest. When the guest molecule contains more than one hydrophobic group, intrahost interactions between the hydrophobes could strongly influence the binding of the guest by its host. In a series of ornithine derivatives functionalized with aromatic hydrophobes, the most electron-rich compound displayed the strongest binding, despite its lowest intrinsic hydrophobicity.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.

Formal arylation of NH3 to produce diphenylamines over supported Pd catalysts

In the presence of supported Pd nanoparticle catalysts, e.g., Pd/Al2O3, various diphenylamines could be synthesized through acceptorless formal arylation using NH3 or its surrogates, e.g., urea, as nitrogen sources and cyclohexanones as arylation sources. The observed catalysis was truly heterogeneous, and the catalyst was reusable with retention of its high catalytic performance.

Selective synthesis of primary anilines from cyclohexanone oximes by the concerted catalysis of a Mg-Al layered double hydroxide supported Pd catalyst

Although the selective conversion of cyclohexanone oximes to primary anilines would be a good complement to the classical synthetic methods for primary anilines, which utilize arenes as the starting materials, there have been no general and efficient methods for the conversion of cyclohexanone oximes to primary anilines until now. In this study, we have successfully realized the efficient conversion of cyclohexanone oximes to primary anilines by utilizing a Mg-Al layered double hydroxide supported Pd catalyst (Pd(OH)x/LDH) under ligand-, additive-, and hydrogen-acceptor-free conditions. The substrate scope was very broad with respect to both cyclohexanone oximes and cyclohexenone oximes, which gave the corresponding primary anilines in high yields with high selectivities (17 examples, 75% to >99% yields). The reaction could be scaled up (gram-scale) with a reduced amount of the catalyst (0.2 mol %). Furthermore, the one-pot synthesis of primary anilines directly from cyclohexanones and hydroxylamine was also successful (five examples, 66-99% yields). The catalysis was intrinsically heterogeneous, and the catalyst could be reused for the conversion of cyclohexanone oxime to aniline at least five times with keeping its high catalytic performance. Kinetic studies and several control experiments showed that the high activity and selectivity of the present catalyst system were attributed to the concerted catalysis of the basic LDH support and the active Pd species on LDH. The present transformation of cyclohexanone oximes to primary anilines proceeds through a dehydration/dehydrogenation sequence, and herein the plausible reaction mechanism is proposed on the basis of several pieces of experimental evidence.

Highly chemoselective reduction of azides to amines by Fe(0) nanoparticles in water at room temperature

A highly chemoselective reduction of aryl, heteroaryl, acyl and sulfonyl azides to the corresponding amines has been achieved by Fe(0) nanoparticles in water at room temperature in the absence of external hydride source. Several readily reducible functionalities including alkene, alkyne, S-S linkage, OTBDMS remain unaffected during reduction.