3-Methyldiphenylamine
[CAS# 1205-64-7]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 3-Methyldiphenylamine
• Synonyms: N-Phenyl-m-toluidine
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.25
• CAS Registry Number: 1205-64-7
• EC Number: 214-885-8
• SMILES: CC1=CC(=CC=C1)NC2=CC=CC=C2

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*,1.066 g/mL (Expl.)
• Melting point: 25-27 ºC (Expl.)
• Index of Refraction: 1.622, Calc.^*. 1.635 (Expl.)
• Boiling Point: 317.3±0.0 ºC (760 mmHg), Calc.^*, 315 ºC (724 mmHg) (Expl.)
• Flash Point: 147.4±14.7 ºC, Calc.^*, 147 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovory and Applicatios

3-Methyldiphenylamine is an organic compound belonging to the class of diphenylamine derivatives, which are known for their diverse applications in various fields including the pharmaceutical industry, agriculture, and material science. It consists of a diphenylamine core with a methyl group attached to the third position of one of the aromatic rings. This substitution influences both the physical and chemical properties of the molecule, offering unique characteristics that make 3-methyldiphenylamine a useful intermediate in synthetic chemistry.

The discovery of 3-methyldiphenylamine dates back to the early 20th century when the chemical family of diphenylamines was first explored for their potential uses in dyes and other industrial chemicals. These compounds, including 3-methyldiphenylamine, are derivatives of diphenylamine, which was first synthesized in the mid-1800s. The methyl group at the 3-position of the aromatic ring in 3-methyldiphenylamine is a crucial modification, as it enhances certain electronic properties, such as solubility and reactivity, which make it a useful building block in various chemical reactions.

In the field of materials science, 3-methyldiphenylamine plays a significant role as an antioxidant and stabilizer in various polymers and plastics. Its ability to inhibit the oxidative degradation of materials has led to its incorporation into products like rubber and other elastomers. The methyl group at the 3-position contributes to the stability of the compound by preventing excessive degradation when exposed to light, heat, and air. This property makes 3-methyldiphenylamine a key additive in the production of materials that require long-term durability, such as automobile tires and industrial coatings.

The compound is also employed in the synthesis of other chemicals, such as agrochemicals and pharmaceuticals. In particular, 3-methyldiphenylamine serves as an important intermediate in the preparation of certain herbicides and fungicides. The compound’s ability to undergo various chemical reactions, including alkylation and halogenation, allows it to be readily modified into a range of functional derivatives suitable for use in pest control. Its versatility in chemical synthesis makes it a valuable compound in the development of new agrochemical agents that can improve crop yields and reduce the impact of plant diseases.

3-Methyldiphenylamine also finds application in the synthesis of dyes and pigments. As a precursor in the production of certain aniline-based dyes, it is used to create vivid colorants for textiles and plastics. The electronic properties imparted by the methyl substitution allow for the development of more vibrant and stable colors in the final product. The dyeing industry relies on such compounds to enhance the quality of fabrics, ensuring they maintain their color and resistance to fading over time.

In addition to its industrial applications, 3-methyldiphenylamine has shown promise in the field of organic electronics. Its ability to act as a charge-transport material has made it a candidate for use in organic light-emitting diodes (OLEDs) and organic solar cells. The compound’s molecular structure and electronic properties allow it to facilitate the movement of charge carriers in these devices, contributing to the efficiency and stability of the overall device. Research into the use of 3-methyldiphenylamine in the development of next-generation organic electronic materials is ongoing, with a focus on improving the performance and lifespan of OLED displays and flexible solar cells.

Despite its wide range of applications, 3-methyldiphenylamine does not come without safety concerns. As with many chemical compounds, proper handling and regulation are essential to minimize exposure risks. The compound can be toxic if ingested or inhaled in large amounts, and appropriate safety measures should be taken when working with it in laboratory or industrial settings. Environmental impact studies have also raised concerns about its persistence in soil and water, highlighting the need for careful disposal and management of waste materials containing 3-methyldiphenylamine.

In conclusion, 3-methyldiphenylamine is a versatile compound with a wide array of applications in materials science, agrochemicals, dye production, and organic electronics. Its unique properties, particularly the presence of the methyl group at the 3-position, make it an important building block for a variety of chemical processes and industrial products. While its benefits are numerous, ongoing research is required to address potential environmental and safety concerns associated with its use.

References

2016. Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes. Synlett.
DOI: 10.1055/s-0035-1562104

2017. Oxidative Biaryl Coupling of N-Aryl Anilines by Using a Hypervalent Iodine(III) Reagent. Synlett.
DOI: 10.1055/s-0036-1590875

2020. Advances in Carbon-Element Bond Construction under Chan-Lam Cross-Coupling Conditions: A Second Decade. Synthesis.
DOI: 10.1055/s-0040-1705971