N-(3-Hydroxyphenyl)-4-toluidine
[CAS# 61537-49-3]

Identification

• Classification: Pharmaceutical intermediate >> Diphenylamine intermediate
• Name: N-(3-Hydroxyphenyl)-4-toluidine
• Synonyms: 3-[(4-Methylphenyl)amino]phenol
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.25
• CAS Registry Number: 61537-49-3
• EC Number: 262-832-2
• SMILES: CC1=CC=C(C=C1)NC2=CC(=CC=C2)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.653, Calc.^*
• Boiling Point: 358.9±17.0 ºC (760 mmHg), Calc.^*
• Flash Point: 151.0±11.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

N-(3-Hydroxyphenyl)-4-toluidine, also known as 3-hydroxy-N-(4-methylphenyl)aniline, is an organic compound with the chemical formula C13H13N O. This substance is characterized by the presence of a hydroxyl group and an amine group, which contribute to its reactivity and potential applications in various fields, including dye chemistry and pharmaceuticals.

The discovery of N-(3-hydroxyphenyl)-4-toluidine can be traced back to the late 19th and early 20th centuries when researchers were investigating aniline derivatives and their properties. Aniline itself, a compound derived from benzene, was first isolated in 1826 and became a cornerstone in the development of synthetic dyes and other chemical products. The synthesis of N-(3-hydroxyphenyl)-4-toluidine is typically accomplished through various methods, including the reaction of 3-hydroxyaniline with p-toluidine under specific conditions, resulting in the formation of the desired compound.

N-(3-hydroxyphenyl)-4-toluidine has garnered attention for its role in the dye industry, particularly in the production of azo dyes. These dyes are widely used in textiles, plastics, and food products due to their vibrant colors and stability. The presence of both the hydroxyl and amino functional groups in N-(3-hydroxyphenyl)-4-toluidine allows it to act as a coupling component in azo dye synthesis. When coupled with diazonium salts, it can yield various azo compounds with distinct color properties. This application highlights the compound's significance in the development of synthetic dyes and pigments, making it essential for industries reliant on colorants.

In addition to its role in dye chemistry, N-(3-hydroxyphenyl)-4-toluidine has been explored for its potential biological activities. Research has indicated that certain aniline derivatives possess antitumor, antimicrobial, and anti-inflammatory properties, leading to interest in their use in medicinal chemistry. While specific studies on N-(3-hydroxyphenyl)-4-toluidine are limited, its structural features suggest it may exhibit similar biological activities, warranting further investigation into its pharmacological potential.

Moreover, N-(3-hydroxyphenyl)-4-toluidine is utilized in the synthesis of various chemical intermediates, which can be employed in the production of agrochemicals, pharmaceuticals, and polymer additives. Its ability to participate in nucleophilic substitution reactions and other organic transformations makes it a valuable building block for developing more complex chemical structures.

Despite its utility, safety considerations are crucial when working with N-(3-hydroxyphenyl)-4-toluidine. Anilines and their derivatives can pose health risks, including potential carcinogenicity and toxicity. Proper handling, including the use of personal protective equipment and adherence to safety guidelines, is essential in laboratory and industrial settings.

In summary, N-(3-hydroxyphenyl)-4-toluidine is a significant organic compound with a rich history of discovery and diverse applications in dye chemistry, medicinal research, and chemical synthesis. Its unique structural features and potential biological activities continue to make it a subject of interest in various scientific disciplines, underscoring its relevance in both industrial and research contexts.