2-(2-aminophenyl)aniline

Molecular formula: C₁₂H₁₂N₂
CAS Number: 553-00-4
IUPAC Name: 2-(2-aminophenyl)aniline
Molecular Weight: 184.24g/mol
Melting Point: (Celsius)
Boiling Point: (Celsius)
Density: 1.2200g/cm3
Synonyms: 2, 2'-BIPHENYLDIAMINE

Interesting facts

Interesting Facts about 2-(2-Aminophenyl)aniline

2-(2-Aminophenyl)aniline, also known as an anthranilic derivative, is a fascinating compound in the realm of organic chemistry. It exhibits several intriguing characteristics and applications that make it a topic of interest for both researchers and students. Here are some key points to consider:

Unique Structure

This compound features a biphenyl structure where two phenyl rings are linked by an amine group, creating a rich site for chemical reactivity.
The presence of the amino group (-NH₂) allows it to participate in a variety of chemical reactions, such as nucleophilic substitution and redox reactions.

Applications in Dyes and Pigments

2-(2-Aminophenyl)aniline is recognized for its potential use in the synthesis of various dyes, notably azo dyes, which are used to impart vibrant colors in textiles.
Its ability to form chelates with metal ions can also make it valuable in developing pigments with enhanced stability and colorfastness.

Pharmaceutical Significance

This compound may provide a scaffold for designing novel pharmaceuticals, particularly in the field of anti-cancer agents, due to its ability to engage in multiple types of binding interactions with biological targets.
Research has indicated that analogs of this compound exhibit significant biological activity, opening pathways for medicinal chemistry explorations.

Noteworthy Reactions

The compound's amino and phenyl groups facilitate a wide range of reactions, making it a versatile intermediate. Common reaction pathways include:

Amination reactions: Allowing the introduction of additional functional groups.
Electrophilic aromatic substitutions: Enabling further functionalization of the aromatic rings.