2,6-Diethyl-4-methylaniline
[CAS 24544-08-9]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: 2,6-Diethyl-4-methylaniline
• Synonyms: 2,6-Diethyl-p-toluidine
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.26
• CAS Registry Number: 24544-08-9
• EC Number: 246-307-5
• SMILES: CCC1=CC(=CC(=C1N)CC)C

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Boiling point: 259.1±9.0 °C 760 mmHg (Calc.)^*
• Flash point: 111.7±14.0 °C (Calc.)^*
• Index of refraction: 1.539 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312-H302-H312
• Safety Statements: P264-P270-P280-P301+P317-P302+P352-P317-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,6-Diethyl-4-methylaniline is an alkyl-substituted aromatic amine that belongs to the group of substituted anilines. The compound is characterized by an aniline structure containing an amino group attached to a benzene ring, with ethyl substituents at the 2 and 6 positions and a methyl substituent at the 4 position. Its chemical structure gives it properties associated with sterically hindered aromatic amines, including moderate basicity, hydrophobicity, and usefulness as an intermediate in organic synthesis.

The discovery and early development of substituted anilines were closely connected with the growth of synthetic organic chemistry during the nineteenth and twentieth centuries. Aniline itself was first isolated in the nineteenth century and became one of the most important aromatic amines because of its role in the production of dyes and chemical intermediates. As the chemical industry expanded, numerous alkyl-substituted anilines were synthesized to modify the physical and chemical properties of the parent aniline structure. Compounds such as 2,6-diethyl-4-methylaniline were developed as members of this broader class of sterically modified aromatic amines.

The synthesis of 2,6-diethyl-4-methylaniline is based on established aromatic substitution and alkylation chemistry used for preparing substituted anilines. Industrial and laboratory preparation methods generally involve modification of substituted aromatic precursors followed by introduction or preservation of the amino functionality. The exact synthetic route depends on the desired purity, scale, and intended application.

The molecular structure of 2,6-diethyl-4-methylaniline provides several features that influence its chemical behavior. The amino group attached to the aromatic ring can participate in protonation reactions, forming corresponding anilinium salts with acids. The nitrogen atom can also undergo common amine reactions, including acylation and alkylation. The ethyl and methyl groups attached to the aromatic ring increase the hydrocarbon content of the molecule and contribute to its lipophilic character.

One important characteristic of 2,6-diethyl-4-methylaniline is the steric influence of the two ethyl groups positioned adjacent to the amino group. Ortho substitution around an aniline nitrogen can affect the accessibility and reactivity of the amino functionality. This structural feature is used in the design of many substituted aniline compounds because steric modification can influence chemical stability, solubility, and reaction selectivity.

The primary applications of 2,6-diethyl-4-methylaniline are related to its use as a chemical intermediate. Substituted anilines are widely used as starting materials in the synthesis of agrochemicals, dyes, pigments, pharmaceutical intermediates, and other specialty chemicals. The compound has been investigated and used as a building block in the preparation of molecules where a substituted aromatic amine structure is required.

In agricultural chemistry, alkyl-substituted anilines have played an important role as intermediates in the manufacture of herbicidal and pesticidal compounds. The aniline framework is present in several classes of agricultural chemicals because modifications to the aromatic ring and amino group can produce molecules with specific biological activities. 2,6-Diethyl-4-methylaniline belongs to this chemical family and has been used in synthetic processes associated with substituted aromatic compounds.

The compound is also relevant in general organic synthesis because aromatic amines are versatile functional groups. The amino group can serve as a site for further transformation, allowing chemists to introduce additional chemical structures through controlled reactions. The substituted benzene ring provides a stable framework that can be incorporated into more complex molecules.

The physical and chemical properties of 2,6-diethyl-4-methylaniline result from the combination of its aromatic ring, amino functionality, and alkyl substituents. The molecule has a balance between polar character from the amino group and nonpolar character from the hydrocarbon substituents. This balance influences its behavior in organic solvents and its suitability as an intermediate for chemical manufacturing.

Overall, 2,6-diethyl-4-methylaniline represents an example of a substituted aromatic amine developed through the evolution of synthetic organic chemistry. Its main significance lies in its role as an intermediate for producing more complex chemical compounds, particularly in areas where modified aniline structures are required. Its continued use reflects the importance of substituted aromatic amines in industrial and research chemistry.