N,N-Diethyl-m-toluidine
[CAS# 91-67-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: N,N-Diethyl-m-toluidine
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.26
• CAS Registry Number: 91-67-8
• EC Number: 202-089-3
• SMILES: CCN(CC)C1=CC=CC(=C1)C

Properties

• Density: 0.92
• Boiling point: 97 ºC (17 mmHg)
• Refractive index: 1.535-1.537
• Flash point: 101 ºC

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS09 Danger
• Hazard Statements: H301-H302-H311-H312-H331-H332-H411-H412
• Precautionary Statements: P261-P262-P264-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P316-P317-P321-P330-P361+P364-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

N,N-Diethyl-m-toluidine is an organic compound belonging to the class of aromatic amines, characterized by the presence of two ethyl groups attached to the nitrogen atom and a methyl group on the meta position of the aniline structure. This compound plays a significant role in various industrial applications, particularly in the synthesis of dyes and other organic materials. The discovery of N,N-diethyl-m-toluidine can be traced back to the extensive research into substituted anilines and their derivatives during the late 19th and early 20th centuries.

The synthesis of N,N-diethyl-m-toluidine is achieved through the alkylation of m-toluidine, which itself is derived from toluene. Toluene was first isolated in the early 19th century, and its derivatives, including m-toluidine, were subsequently synthesized through nitration and reduction processes. The alkylation of m-toluidine with diethyl sulfate or ethyl halides in the presence of a base facilitates the introduction of the ethyl groups, resulting in the formation of N,N-diethyl-m-toluidine. This method of synthesis has been refined over the years, allowing for improved yields and purity of the product.

N,N-Diethyl-m-toluidine is primarily used as an intermediate in the production of azo dyes. Azo dyes are synthetic dyes characterized by the presence of one or more azo groups (-N=N-), and they are widely used in the textile industry due to their vibrant colors and stability. The compound can participate in diazotization reactions followed by coupling with various aromatic compounds to form azo dyes, which are then used to color fabrics, plastics, and other materials. The meta position of the methyl group in N,N-diethyl-m-toluidine enhances its reactivity, making it suitable for the synthesis of specific dye types.

Beyond dye production, N,N-diethyl-m-toluidine is employed in the formulation of rubber and plastics, where it acts as a processing aid and stabilizer. Its ability to scavenge free radicals contributes to the thermal stability of synthetic materials, prolonging their lifespan and improving their performance characteristics. Additionally, N,N-diethyl-m-toluidine is used in the production of pigments and colorants, expanding its applicability in various industrial sectors.

The compound also finds utility in the production of pharmaceuticals and agrochemicals, serving as a building block for more complex organic molecules. Its reactivity allows for the development of diverse functionalized compounds that are crucial in the pharmaceutical industry for drug formulation and synthesis.

While N,N-diethyl-m-toluidine is valuable in industrial applications, safety and environmental considerations have emerged as critical issues. The compound is classified as harmful, with potential risks including skin and respiratory irritation, as well as concerns regarding its carcinogenicity. Regulatory agencies have established guidelines to ensure the safe handling and use of this compound, prompting manufacturers to adopt safer practices and explore alternatives when possible.

Research into N,N-diethyl-m-toluidine continues to evolve, with ongoing studies focusing on its potential applications and safer synthetic methods. The exploration of green chemistry principles aims to minimize the environmental impact associated with its production and use, thereby enhancing its sustainability.

In conclusion, N,N-Diethyl-m-toluidine is a significant aromatic amine with diverse applications in dye manufacturing, rubber production, and pharmaceutical synthesis. Its discovery and subsequent utilization in various industrial processes reflect the ongoing advancements in organic chemistry and materials science. As research progresses, the compound may find new applications and safer methodologies that further enhance its utility across multiple sectors.

References

2021. 1,8-Naphthalimide Derivatives as Dyes for Textile and Polymeric Materials: A Review. Fibers and Polymers, 22(5).
DOI: 10.1007/s12221-021-0979-9

2018. Novel monoazo disperse and cationic dyes: preparation, structure investigation, study of spectroscopic, antibacterial and antifungal potential. Monatshefte für Chemie - Chemical Monthly, 149(2).
DOI: 10.1007/s00706-017-2130-6

2016. Effect of auxiliary electron-donating group on the microscopic nonlinear optical properties of vinyl and azobenzene based chromophores. Journal of Materials Science: Materials in Electronics, 27(6).
DOI: 10.1007/s10854-016-4681-4