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2,4-Dimethyl aniline
[CAS# 95-68-1]

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Identification
ClassificationOrganic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
Name2,4-Dimethyl aniline
Synonyms1-Amino-2,4-dimethylbenzene; 2,4-Dimethyl aminobenzene; 2,4-Dimethylaniline; 2,4-Xylidine
Molecular StructureCAS # 95-68-1, 2,4-Dimethyl aniline
Molecular FormulaC8H11N
Molecular Weight121.18
CAS Registry Number95-68-1
EC Number202-440-0
SMILESCC1=CC(=C(C=C1)N)C
Properties
Density0.98
Melting point16 °C
Boiling point218 °C
Refractive index1.558-1.56
Flash point90 °C
Water solubility5 g/L (20 °C)
Safety Data
Hazard Symbolssymbol symbol symbol symbol   GHS06;GHS07;GHS08;GHS09 Danger  Details
Risk StatementsH301+H311+H331-H301-H311-H319-H330-H331-H373-H411  Details
Safety StatementsP260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P319-P320-P321-P330-P337+P317-P361+P364-P391-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H311
Acute toxicityAcute Tox.3H301
Specific target organ toxicity - repeated exposureSTOT RE2H373
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Acute toxicityAcute Tox.2H330
Eye irritationEye Irrit.2H319
Acute toxicityAcute Tox.3H331
Specific target organ toxicity - repeated exposureSTOT RE1H372
Acute toxicityAcute Tox.4H302
Skin irritationSkin Irrit.2H315
Germ cell mutagenicityMuta.2H341
Transport InformationUN 1711
SDSAvailable
up Discovery and Applications
2,4-Dimethylaniline, an aromatic amine with the chemical formula C9H13N, consists of a benzene ring with two methyl groups and an amino group attached at the 2 and 4 positions. This compound was first synthesized in the late 19th century, reflecting the growing interest in the chemical modifications of aniline derivatives. The synthesis typically involves the alkylation of aniline with methyl groups, providing a straightforward route to obtain this compound.

The primary application of 2,4-dimethylaniline lies in the dye industry. It serves as a vital intermediate in the production of various azo dyes, which are widely used in textiles, plastics, and food industries due to their vibrant colors and stability. The ability of 2,4-dimethylaniline to undergo diazotization reactions allows it to be transformed into a variety of azo compounds, thus making it an essential building block in dye chemistry.

Beyond its role in dye synthesis, 2,4-dimethylaniline has applications in the formulation of agrochemicals. It is utilized in the production of herbicides and pesticides, contributing to the development of compounds that help manage agricultural pests and enhance crop yields. The effectiveness of 2,4-dimethylaniline-derived formulations in protecting plants highlights its significance in modern agriculture.

In addition to its industrial applications, 2,4-dimethylaniline is employed in the manufacture of rubber chemicals. It acts as an accelerator in rubber vulcanization, improving the processing and performance characteristics of rubber products. This application is particularly crucial in the automotive industry, where durable and high-performance rubber components are essential.

Despite its beneficial applications, safety concerns associated with 2,4-dimethylaniline warrant attention. As with many aromatic amines, it is recognized for its potential health risks, including carcinogenicity. Consequently, regulatory bodies have established guidelines for its safe handling and usage in industrial processes. Adequate safety measures, including personal protective equipment and proper ventilation, are essential when working with this compound to minimize exposure and health risks.

Recent research has begun to address the environmental impact of 2,4-dimethylaniline and its derivatives. There is a growing focus on developing more sustainable and environmentally friendly synthesis methods, as well as exploring alternative compounds that could serve similar functions in dye production and agricultural applications. This trend aligns with the broader movement towards sustainability in the chemical industry.

In summary, 2,4-dimethylaniline is an important compound with significant applications in dye synthesis, agrochemicals, and rubber manufacturing. Its discovery has contributed to advancements in these fields, although safety considerations are paramount. Ongoing research aims to enhance its applications while addressing environmental and health concerns associated with its use.

References

2022. Synthesis of Arylamines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-236-00176

2022. Radical Cation Induced Synthesis of 2,3-Disubstituted Quinolines from Anilines and Aliphatic Aldehydes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-00914

2022. Potassium Persulfate Mediated Synthesis of 4-Arylquinolines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-01023
Market Analysis Reports
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