N,N-Dimethylaniline
[CAS# 121-69-7]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: N,N-Dimethylaniline
• Synonyms: DMA
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• CAS Registry Number: 121-69-7
• EC Number: 204-493-5
• SMILES: CN(C)C1=CC=CC=C1

Properties

• Density: 0.956
• Melting point: 1.5-2.5 ºC
• Boiling point: 193-194 ºC
• Refractive index: 1.557-1.559
• Flash point: 63 ºC
• Water solubility: 1 g/L (20 ºC)

Safety Data

• Hazard Symbols: GHS06;GHS08;GHS09 Danger
• Hazard Statements: H301+H311+H331-H351-H411
• Precautionary Statements: P202-P273-P280-P301+P310-P302+P352+P312-P304+P340+P311

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Carcinogenicity	Carc.	2	H351
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Specific target organ toxicity - single exposure	STOT SE	3	H336
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 2253

Discovory and Applicatios

N,N-Dimethylaniline, also known as N,N-dimethyl-aminobenzene, is an organic compound with the molecular formula C9H13N. It is classified as a tertiary amine and is characterized by the presence of two methyl groups attached to a nitrogen atom that is further bonded to a phenyl group. The discovery of N,N-dimethylaniline dates back to the early 20th century, during a period of extensive research into amines and their derivatives, which were recognized for their diverse applications in the chemical industry.

The synthesis of N,N-dimethylaniline typically involves the methylation of aniline using methyl iodide or dimethyl sulfate in the presence of a base. This reaction effectively introduces the two methyl groups onto the nitrogen atom, producing N,N-dimethylaniline. The compound can also be derived from the reduction of N,N-dimethylbenzamide. Its ability to serve as a building block for more complex molecules has led to its widespread use in various chemical syntheses.

N,N-Dimethylaniline has found extensive application in the dye industry, where it serves as an intermediate in the production of various dyes and pigments. It is particularly used in the synthesis of aniline dyes, which are known for their vibrant colors and ability to dye a wide range of materials, including textiles, paper, and leather. The compound's reactivity allows for the introduction of different functional groups, leading to a variety of dye structures tailored for specific applications.

In addition to its role in dye manufacturing, N,N-dimethylaniline is utilized in the production of agricultural chemicals, such as herbicides and fungicides. Its ability to act as a reactive intermediate makes it valuable in the synthesis of active pharmaceutical ingredients and agrochemicals. The compound's nitrogen-containing structure often facilitates biological activity, enhancing its effectiveness in pest control applications.

N,N-Dimethylaniline also plays a significant role in the production of polymers and resins. It is commonly used as a curing agent in epoxy formulations, where it helps to promote cross-linking and enhance the mechanical properties of the final product. This application is particularly important in industries that require durable and resistant materials, such as construction and automotive sectors.

Despite its valuable applications, N,N-dimethylaniline must be handled with caution due to its potential health hazards. It is classified as a toxic and harmful substance, with exposure potentially leading to adverse health effects, including skin irritation, respiratory issues, and central nervous system effects. Regulatory agencies, such as the U.S. Environmental Protection Agency (EPA) and the European Chemicals Agency (ECHA), have established guidelines for its safe use, emphasizing the importance of protective measures and proper handling procedures in industrial settings.

In recent years, there has been growing interest in exploring safer alternatives and more sustainable practices in the chemical industry. This trend includes research into less hazardous compounds and greener synthesis methods, which aim to reduce the environmental impact associated with the use of traditional chemicals like N,N-dimethylaniline.

In conclusion, N,N-dimethylaniline is an important compound with significant applications in the dye, agricultural, and polymer industries. Its discovery and subsequent use underscore the importance of nitrogen-containing organic compounds in chemical synthesis. Ongoing research into its safety and potential alternatives will play a crucial role in shaping the future of its application in various fields.

References

2024. To cyclize or not? Synthesis of heterocycles through electro-oxidation of N,N-dimethylaniline. Chemical Papers, 78(17), 10863�10874.
DOI: 10.1007/s11696-024-03807-6

1883. Ü ber die Azyline, eine homologe Reihe Stickstoffhältiger Basen. Monatshefte für Chemie, 4(1), 505�517.
DOI: 10.1007/bf01516839

1883. Zur Kenntniss der Azyline. Monatshefte für Chemie, 4(1), 518�529.
DOI: 10.1007/bf01517970