o-Anisidine
[CAS# 90-04-0]

Identification

• Classification: Organic raw materials >> Ether compounds and their derivatives >> Halogenation, sulfonation, nitration or nitrosation of ethers, ether alcohols, ether phenols
• Name: o-Anisidine
• Synonyms: 1-Amino-2-methoxybenzene; 2-Aminoanisole; 2-Methoxyaniline
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• CAS Registry Number: 90-04-0
• EC Number: 201-963-1
• SMILES: COC1=CC=CC=C1N

Properties

• Density: 1.092 g/mL (Expl.)
• Melting point: 3-6 ºC (Expl.)
• Boiling point: 225 ºC (Expl.)
• Refractive index: 1.574 (Expl.)
• Flash point: 100 ºC (Expl.)
• Water solubility: 13 g/L (20 ºC)

Safety Data

• Hazard Symbols: GHS06;GHS08;GHS09 Danger
• Hazard Statements: H301+H311+H331-H301-H311-H331-H341-H350-H373-H411
• Precautionary Statements: P203-P260-P261-P262-P264-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P316-P318-P319-P321-P330-P361+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H301
Germ cell mutagenicity	Muta.	2	H341
Carcinogenicity	Carc.	1B	H350
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

• Transport Information: UN 2431

Discovory and Applicatios

o-Anisidine, also known as 2-methoxyaniline, is an organic compound with the molecular formula C7H9NO. It consists of an aniline structure, with a methoxy group (-OCH3) attached to the benzene ring at the ortho position relative to the amino group. This compound is widely studied for its unique chemical properties, and its discovery and applications have contributed significantly to the field of organic chemistry, particularly in dye synthesis, pharmaceuticals, and agrochemicals.

The discovery of o-anisidine dates back to the 19th century, when it was first identified as a derivative of aniline. Its synthesis and chemical reactivity have since been well-documented, and it has become a standard compound in laboratories around the world. The presence of both the amino group and methoxy group makes o-anisidine a versatile intermediate in the synthesis of various chemicals, as these functional groups provide distinct reactivity profiles.

o-Anisidine is primarily used as an intermediate in the manufacture of dyes and pigments. It plays a central role in the synthesis of azo dyes, which are widely used in the textile industry. The methoxy group in o-anisidine allows for enhanced solubility and stability of the resulting dyes, making them ideal for coloring textiles, leather, and even food products. Azo dyes derived from o-anisidine are valued for their bright colors and durability, making this compound a key building block in the global dyeing industry.

Beyond its use in the dye industry, o-anisidine has applications in the synthesis of pharmaceuticals and agrochemicals. It serves as an intermediate in the preparation of various biologically active compounds. One notable application is its role in the synthesis of antimalarial drugs, where it is used as a precursor for the production of quinine analogs. Additionally, o-anisidine is employed in the synthesis of herbicides and fungicides, contributing to the development of agrochemicals that protect crops from pests and diseases.

Another significant application of o-anisidine is in the field of organic electronics. Research into the use of o-anisidine derivatives in organic semiconductors has increased in recent years, with the compound being explored for its potential in light-emitting diodes (LEDs), organic solar cells, and organic field-effect transistors (OFETs). The unique electronic properties of o-anisidine, especially its ability to conduct charge, make it a valuable material for organic electronic devices that are lightweight, flexible, and cost-effective.

Furthermore, o-anisidine has been investigated for its potential use in the field of chemical sensors. Due to its reactivity with various metal ions and other substances, o-anisidine-based sensors can be developed for the detection of pollutants or other chemicals in the environment. These sensors can be used for monitoring water quality, air pollution, and industrial processes.

In conclusion, o-anisidine is an important chemical with diverse applications in various industries. Its role as a precursor for dyes, pharmaceuticals, and agrochemicals highlights its versatility and importance in industrial chemistry. The continued research into its applications in electronics and environmental monitoring demonstrates the compound’s ongoing relevance in the modern world.

References

2024. Chloroacetates of Substituted 1H-Indol-5-,6-,7-Ylamines and Their Antimicrobial Activity. Pharmaceutical Chemistry Journal, 58(1).
DOI: 10.1007/s11094-024-03047-8

2024. Synthesis and Characterization of Poly(o-anisidine-co-o-toluidine)/PCBM Composites for Optoelectronic Applications. Journal of Inorganic and Organometallic Polymers and Materials, 34(5).
DOI: 10.1007/s10904-024-03090-8

2023. Synthesis of positional isomer and analogues of neostigmine methylsulfate: an anticholinesterase agent. Chemical Papers, 77(10).
DOI: 10.1007/s11696-023-02891-4