Di-p-tolylamine
[CAS# 620-93-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: Di-p-tolylamine
• Synonyms: 4-methyl-N-(4-methylphenyl)aniline
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.28
• CAS Registry Number: 620-93-9
• EC Number: 210-659-8
• SMILES: CC1=CC=C(C=C1)NC2=CC=C(C=C2)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 78-82 °C (Expl.)
• Index of Refraction: 1.611, Calc.^*
• Boiling Point: 330.5±0.0 °C (760 mmHg), Calc.^*
• Flash Point: 167.6±14.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

Di-p-tolylamine, also known as N,N'-dimethyl-p-toluidine, is a chemical compound that consists of two p-tolyl groups attached to a nitrogen atom. This aromatic amine is a derivative of toluidine, which itself is a methylated aniline compound. Di-p-tolylamine was first synthesized in the early 20th century during efforts to study the properties and reactivity of amines and their derivatives. Over time, the compound has become known for its applications in various fields, including industrial chemistry, organic synthesis, and as a precursor for the manufacture of specialty chemicals.

The discovery of di-p-tolylamine can be attributed to the early exploration of amines in organic chemistry. Amines, especially those derived from aromatic compounds like aniline, have long been of interest due to their reactivity and versatility in synthesis. Di-p-tolylamine is synthesized through the alkylation of aniline using p-tolyl groups, which involves the introduction of a methyl group (-CH3) onto the aromatic ring of the aniline derivative. The resulting compound exhibits the properties of both a simple amine and a substituted aromatic compound, giving it a range of potential applications.

One of the primary applications of di-p-tolylamine is in organic synthesis, where it is used as a building block for the preparation of other chemical compounds. It serves as an important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. Di-p-tolylamine is often employed in the production of dyes, pigments, and other colorants, as it can readily undergo reactions that introduce different functional groups, allowing for the creation of complex molecules. Its ability to participate in electrophilic aromatic substitution reactions makes it valuable in the formation of various derivatives with different substituents.

In addition to its use in organic synthesis, di-p-tolylamine has applications in the polymer industry. It can act as a curing agent for certain types of resins, particularly in the production of polyurethane and epoxy-based materials. When combined with specific hardeners or cross-linking agents, di-p-tolylamine can enhance the hardness and durability of polymer products, making them suitable for use in coatings, adhesives, and sealants. The compound’s ability to influence the properties of resins has made it a valuable ingredient in industrial formulations that require enhanced performance and stability.

Di-p-tolylamine also has applications in the synthesis of specific chemical compounds that are used in the field of electronics and electrical engineering. In particular, it can be utilized in the preparation of certain surfactants and corrosion inhibitors. Surfactants, which reduce surface tension, are used in cleaning agents, detergents, and emulsifiers, while corrosion inhibitors are employed to protect metal surfaces from degradation. The presence of the p-tolyl groups in di-p-tolylamine enhances its ability to interact with other chemicals, providing it with unique properties for these industrial applications.

Additionally, di-p-tolylamine has been studied for its potential use in the synthesis of advanced materials, such as organic semiconductors and optoelectronic devices. Its structural characteristics make it suitable for incorporation into organic thin-film transistors and organic light-emitting diodes (OLEDs), both of which are promising technologies in the field of flexible electronics. Researchers have explored the compound’s ability to act as a hole-transporting material, which is a critical component in the development of efficient OLEDs and organic solar cells.

In conclusion, di-p-tolylamine is a versatile chemical compound with a variety of applications in organic synthesis, industrial chemistry, and materials science. Its synthesis and reactivity have made it an important intermediate in the production of numerous chemical products, from dyes and pigments to resins and electronic materials. As research into its applications continues, di-p-tolylamine is likely to remain a valuable compound in the development of new technologies and industrial processes.

References

2021. Buchwald-Hartwig reaction: an update. Monatshefte für Chemie - Chemical Monthly, 152(8).
DOI: 10.1007/s00706-021-02834-3

2006. One-Pot Synthesis of Symmetrical Di- and Triarylamines Using Urea as the Source of the Amino Group. Synlett.
DOI: 10.1055/s-2005-923596

2006. Urea as ammonia equivalent in aryl halides amination catalyzed by palladium complexes. Russian Journal of Organic Chemistry, 42(11).
DOI: 10.1134/s1070428006110133