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2-Ethylaminotoluene
[CAS# 94-68-8]

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Identification
Classification Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
Name 2-Ethylaminotoluene
Synonyms N-Ethyl-o-toluidine
Molecular Structure CAS # 94-68-8, 2-Ethylaminotoluene, N-Ethyl-o-toluidine
Molecular Formula C9H13N
Molecular Weight 135.21
CAS Registry Number 94-68-8
EC Number 202-354-3
SMILES CCNC1=CC=CC=C1C
Properties
Density 0.938 g/mL
Melting point -15 ºC
IBoiling point 218 ºC
Refractive index 1.546-1.548
Flash point 88 ºC
Water solubility insoluble
Safety Data
Hazard Symbols symbol symbol symbol   GHS06;GHS07;GHS08 Danger    Details
Hazard Statements H301-H311-H315-H319-H331-H335-H351-H370-H373    Details
Precautionary Statements P203-P260-P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P308+P316-P316-P318-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H301
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Specific target organ toxicity - single exposureSTOT SE1H370
Specific target organ toxicity - repeated exposureSTOT RE2H373
CarcinogenicityCarc.2H351
Acute toxicityAcute Tox.3H311
Acute toxicityAcute Tox.3H331
Skin irritationSkin Irrit.2H315
CarcinogenicityCarc.1BH350
Acute toxicityAcute Tox.2H310
Acute toxicityAcute Tox.2H330
Acute toxicityAcute Tox.2H300
Acute toxicityAcute Tox.4H330
Chronic hazardous to the aquatic environmentAquatic Chronic3H412
SDS Available
up Discovory and Applicatios
2-Ethylaminotoluene, also known as 2-(ethylamino)toluene, is an organic compound that falls under the category of aromatic amines. It is characterized by an ethylamino group attached to a toluene ring at the ortho position. The discovery of 2-ethylaminotoluene can be traced back to the early 20th century when chemists began systematically studying substituted toluenes and their derivatives. The compound is synthesized through the alkylation of aniline with ethyl bromide, a method that has been refined over the years to yield high purity products.

The applications of 2-ethylaminotoluene are primarily found in the fields of dye synthesis and organic chemistry. One of its most significant roles is as an intermediate in the production of various azo dyes. Azo dyes, characterized by their vivid colors, are widely used in textile manufacturing, printing, and food industries. The ability of 2-ethylaminotoluene to undergo diazotization reactions makes it an essential precursor for synthesizing these dyes, contributing to its importance in industrial applications.

In addition to its role in dye production, 2-ethylaminotoluene has potential applications in pharmaceuticals. Its structure allows for further chemical modifications, enabling the synthesis of various biologically active compounds. Research into the pharmacological properties of derivatives of 2-ethylaminotoluene has shown promise in developing new therapeutic agents, particularly in the fields of analgesics and anti-inflammatory drugs.

Furthermore, 2-ethylaminotoluene is utilized in the synthesis of polymers and resins. Its amine functional group can participate in cross-linking reactions, contributing to the production of thermosetting plastics. This application is particularly relevant in industries where durable materials are required, such as automotive and aerospace sectors.

Despite its useful applications, the safety profile of 2-ethylaminotoluene warrants attention. Like many aromatic amines, it poses potential health risks, including carcinogenicity. Regulatory bodies have established guidelines for its safe handling and usage in industrial processes. Proper safety measures, including personal protective equipment and adequate ventilation, are crucial when working with this compound to minimize exposure and health risks.

Recent research has focused on the environmental impact of aromatic amines, including 2-ethylaminotoluene. Efforts are underway to develop greener synthesis methods and explore more sustainable alternatives for dye production and other applications. This shift towards sustainability reflects the growing awareness of environmental concerns associated with chemical manufacturing.

In conclusion, 2-ethylaminotoluene is an important compound in organic chemistry with significant applications in dye synthesis, pharmaceuticals, and polymer production. 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.

References

2016. Introduction of C-Nitrogen by Palladium-Catalyzed Cross Coupling with Amines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-110-00871
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