3-Amino-1,2,3,4-tetrahydrocarbazol
[CAS# 61894-99-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Carbazoles
• Name: 3-Amino-1,2,3,4-tetrahydrocarbazol
• Synonyms: 2,3,4,9-Tetrahydro-1H-carbazol-3-amine
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.26
• CAS Registry Number: 61894-99-3
• SMILES: C1CC2=C(CC1N)C3=CC=CC=C3N2

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.677, Calc.^*
• Boiling Point: 362.5±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 200.5±15.1 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P280-P305+P351+P338

Discovory and Applicatios

3-Amino-1,2,3,4-tetrahydrocarbazol is an organic compound belonging to the class of tetrahydrocarbazoles, which are nitrogen-containing heterocycles. This compound features an amino group at the third position of the tetrahydrocarbazole framework, contributing to its unique properties and reactivity. The discovery of this compound can be traced back to research focused on the synthesis of nitrogen-containing heterocycles, which has gained considerable interest due to their diverse applications in medicinal chemistry and materials science.

The synthesis of 3-amino-1,2,3,4-tetrahydrocarbazol typically involves the reduction of carbazole derivatives, often through catalytic hydrogenation processes. The reduction of carbazole or its derivatives provides a pathway to introduce the amino group, enabling the formation of this compound. This synthetic route has been optimized in various studies to improve yield and selectivity, showcasing the compound's relevance in organic synthesis.

3-Amino-1,2,3,4-tetrahydrocarbazol has gained attention for its potential applications in the pharmaceutical industry. The presence of the amino group enhances the compound's reactivity, allowing for further functionalization and modification, which is crucial in drug design. Compounds with a similar structure have been studied for their biological activities, including antitumor and antimicrobial properties. The ability to modify the tetrahydrocarbazole framework by introducing various substituents at different positions offers a promising avenue for developing novel therapeutic agents.

In addition to its pharmaceutical applications, 3-amino-1,2,3,4-tetrahydrocarbazol has been investigated for its potential as a precursor in the synthesis of advanced materials. The compound can serve as a building block in the production of polymers, dyes, and other materials, leveraging its nitrogen content for crosslinking and other reactions. This versatility highlights the compound's importance in material science, where it may contribute to the development of functional materials with specific properties.

Research has also explored the role of 3-amino-1,2,3,4-tetrahydrocarbazol in the field of organic electronics. Due to its unique electronic properties, compounds in this class may find applications in organic light-emitting diodes (OLEDs), organic photovoltaics, and other electronic devices. The incorporation of nitrogen heterocycles in organic electronic materials can enhance charge transport and improve device performance.

Furthermore, the environmental impact of synthesizing and using 3-amino-1,2,3,4-tetrahydrocarbazol is an area of ongoing study. As with many nitrogen-containing compounds, there are concerns about toxicity and environmental persistence. Research into safer synthetic methods and the development of greener chemistry practices is crucial to mitigate any negative environmental effects associated with this compound.

In summary, 3-amino-1,2,3,4-tetrahydrocarbazol is a nitrogen-containing heterocyclic compound with significant potential in pharmaceutical and material science applications. Its unique structure allows for further chemical modifications, making it valuable in drug design and the synthesis of advanced materials. Ongoing research into its biological activities and environmental implications will help to better understand and optimize its applications in various fields.