8-Amino-3,4-dihydro-1(2H)-naphthalenone
[CAS# 210346-49-9]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Naphthalenes
• Name: 8-Amino-3,4-dihydro-1(2H)-naphthalenone
• Synonyms: 8-Amino-3,4-dihydro-2H-naphthalen-1-one; 8-Amino-3,4-dihydronaphthalen-1(2H)-one
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.20
• CAS Registry Number: 210346-49-9
• SMILES: C1CC2=C(C(=O)C1)C(=CC=C2)N

Properties

• Solubility: Very slightly soluble (0.4 g/L) (25 °C), Calc.^*
• Density: 1.193±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 84-85 °C^**, (Expl.)
• Index of Refraction: 1.620, Calc.^*
• Boiling Point: 342.4±31.0 °C (760 mmHg), Calc.^*
• Flash Point: 160.9±24.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Nakamura, Katsutaro

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

8-Amino-3,4-dihydro-1(2H)-naphthalenone is an organic compound that has garnered attention for its potential applications in medicinal chemistry and materials science. It features a naphthalene ring system, a key structural motif in organic chemistry, which is fused with a ketone and an amino group at specific positions on the aromatic ring. The compound's unique structure offers interesting possibilities for both synthetic and biological applications.

The discovery of 8-amino-3,4-dihydro-1(2H)-naphthalenone is rooted in the exploration of naphthalene derivatives, which have long been studied due to their diverse biological activities. The presence of the amino group on the naphthalene ring confers the potential for interaction with biological systems, making it an attractive candidate for drug discovery. The dihydro naphthalenone structure is notable for its chemical reactivity and stability, which has facilitated its use as an intermediate in the synthesis of various organic compounds.

One of the key applications of 8-amino-3,4-dihydro-1(2H)-naphthalenone lies in the field of medicinal chemistry. The compound's ability to interact with biological targets, such as enzymes, receptors, and proteins, makes it a valuable scaffold for the development of novel drug candidates. Studies have suggested that naphthalene-based compounds can exhibit anti-inflammatory, anticancer, and antimicrobial properties, depending on the functional groups attached to the aromatic ring. In particular, the amino group on 8-amino-3,4-dihydro-1(2H)-naphthalenone may facilitate its ability to form hydrogen bonds with biological targets, improving its binding affinity and therapeutic potential.

In addition to its role in drug development, 8-amino-3,4-dihydro-1(2H)-naphthalenone is utilized in the synthesis of more complex organic molecules. Its structure enables it to act as a building block for the creation of larger, multifunctional compounds, which can be tailored for specific applications. In materials science, the compound’s stability and reactivity make it a candidate for use in the production of organic semiconductors, dyes, and sensors. Furthermore, the versatile nature of the naphthalene ring system allows for modification of the molecule to achieve desired optical or electronic properties, making it a potential material for use in advanced electronic devices.

The synthetic versatility of 8-amino-3,4-dihydro-1(2H)-naphthalenone also makes it a useful intermediate in the production of polymers and other complex materials. Its incorporation into larger molecular frameworks allows for the creation of specialized materials with tailored properties for applications in electronics, coatings, and other industries. Additionally, it has been explored in the development of functionalized nanomaterials, where its chemical structure can be fine-tuned to enhance performance in various applications.

In conclusion, 8-amino-3,4-dihydro-1(2H)-naphthalenone is a valuable compound in both medicinal chemistry and materials science. Its ability to serve as a precursor for drug development and functional materials underscores its versatility and importance. As research into naphthalene derivatives continues, the compound is expected to play a role in the advancement of new therapeutic agents and cutting-edge technologies.

References

2003. A Convenient Synthesis of 7-Halo-1-indanones and 8-Halo-1-tetralones. *The Journal of Organic Chemistry*, 68(25).
DOI: 10.1021/jo035289s