66640-75-3

Usage

Derivative of naphthalene

1-Amino-5-iodonaphthalene is derived from the parent compound naphthalene, which is a polycyclic aromatic hydrocarbon consisting of two fused benzene rings.

Amino group

The compound contains an amino group (-NH2), which is a functional group consisting of a nitrogen atom bonded to two hydrogen atoms, contributing to its reactivity and chemical properties.

Iodine atom

The presence of an iodine atom in the compound enhances its reactivity and contributes to its physical and chemical properties, such as fluorescence.

Reactant in organic synthesis

1-Amino-5-iodonaphthalene is commonly used as a reactant in various organic synthesis reactions, leading to the formation of diverse chemical compounds.

Starting material for pharmaceuticals and dyes

The compound serves as a starting material for the preparation of various pharmaceuticals and dyes due to its versatile chemical structure and properties.

Production of fluorescent dyes

1-Amino-5-iodonaphthalene is used in the production of fluorescent dyes, which have a wide range of applications in different fields.

Fluorescent probe in biochemical studies

The compound's fluorescent properties make it a useful tool in biochemical research, allowing for the tracking and visualization of biological processes.

Fluorescent properties

1-Amino-5-iodonaphthalene is known for its ability to emit light upon excitation, making it useful in various applications in the fields of chemistry, biology, and materials science.

Antimicrobial and antitumor activities

The compound exhibits potential antimicrobial and antitumor activities, which makes it a subject of interest in medicinal chemistry research and drug development.

Upstream product

• 64567-10-8 1-Iodo-5-nitronaphthalene 
• 3272-91-1 5-nitro-[1]naphthylamine 
• 605-71-0 1,5-dinitronaphthalene 

Relevant academic research and scientific papers

Direct cyanation of picolinamides using K4[Fe(CN)6] as the cyanide source

The efficient, simple, and environment-friendly route of direct cyanation of picolinamides has been developed with nontoxic K4[Fe(CN)6] as the cyanide source through Pdcatalyzed C-H bond activation. A series of N-(naphthalene-1- yl)picolinamide derivatives were successfully transformed to the corresponding cyanation products. The cyanation mechanism has also been speculated.

Synthesis of 1,5-naphthylethynyl nanostructure networks with extended π-conjugation. Effective heterocoupling catalyzed by palladium under a compatible CO2 atmosphere

The synthesis of a new extended π-conjugated 5-N,N-dimethylaminonaphthyl family was undertaken by palladium-catalyzed cross-coupling reaction between a protected 5-iodonaphthylethynyl and 1-ethynyl-5-(N,N-dimethylamino)naphthalene. Under an argon atmosphere, only the homocoupling product 1,4-(N,N-dimethylamino)naphthyl-1,3-butadiyne was isolated, in excellent yield. However, under a compatible and pure carbon dioxide atmosphere, the cross-coupling product was obtained in excellent yield.

Carbon networks based on 1,5-naphthalene units. Synthesis of 1,5-naphthalene nanostructures with extended π-conjugation

The synthesis and spectroscopic characterization of nanometer-sized conjugated molecules of 5-X-naphthylethynyl (X= NO2, NMe2) units with precise length and constitution have been carried out. A new extended π-conjugated 5-nitronaphthyl family was synthesized by palladium-catalyzed cross-coupling reaction between the protected 5-iodonaphthylethynyl 5a and 1-ethynyl-5-nitronaphthalene 9, or the resulting ethynyl compound 11 and the 1-iodo-5-nitronaphthalene 3. Catalytic oxidative dimerization of the terminal acetylene compounds permits the isolation of the corresponding 1,3-butadiyne derivatives 16-18, with the nitro groups at the ends of the conjugation, in excellent yields. A new family of conjugated 5-nitro-(naphthylethynyl)-[5-(N,N-dimethylamino)]-naphthalene (20-22), was also synthesized by palladium-catalyzed cross-coupling reaction between 5-iodo-N,N-dimethylnaphthalene-1-amine (19) with the appropriate terminal acetylene (9, 11, and 13 respectively). Compounds 20-22 show a fluorescence emission and also exhibit a charge-transfer absorption in the visible spectrum. X-ray structure of 20 confirms a centrosymmetric dimer association with an interplanar distance of 3.43 A, and the naphthalene rings adopt an anti conformation around the C≡C triple bond.