64567-10-8

Usage

Chemical structure

Consists of a naphthalene ring with a nitro group at the 5-position and an iodine atom at the 1-position.

Physical state

Yellow solid.

Molecular weight

281.06 g/mol.

Uses

Commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds, and in research and development applications such as the study of organic reactions and the synthesis of new materials.

Handling precautions

Potentially hazardous, should be used in a well-ventilated area with appropriate protective equipment.

Upstream product

• 605-71-0 1,5-dinitronaphthalene 
• 2243-62-1 1,5-naphthalenediamine 
• 86-57-7 1-Nitronaphthalene 
• 3272-91-1 5-nitro-[1]naphthylamine 

Downstream Products

• 66640-75-3 5-iodonaphthalene-1-amine 

Relevant academic research and scientific papers

A methyl ketone bridged molecule as a multi-stimuli-responsive color switch for electrochromic devices

A new multi-stimuli-responsive molecular switch M5 with a methyl ketone bridge has been developed to fabricate a visible-near infrared absorbing electrochromic device. The basochromic and electrochromic properties of methyl ketone M5 with nitronaphthalene

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.

Iodination of nitroarenes by a superactive reagent based on iodine chloride

Iodine chloride reacts with Ag2SO4 in H2SO4 to give a new superelectrophilic reagent capable of iodinating nitrobenzene, halogenated nitrobenzenes, nitrotoluenes, and aromatic compounds with two nitro groups in the ring. Mononitroarenes are easily iodinated at 0-20 deg C, while dinitroarenes require heating to 100-170 deg C.

Lodination of deactivated aromatic compounds with iodine chloride

Iodine(I) chloride reacts with deactivated arenes in sulfuric acid to give the corresponding aryl iodides whose yield strongly depends on the concentration of H2SO4. The optimal concentration of the latter was determined for iodination of aromatic carboxylic acids and halobenzenes. 1998 MAHK Hayka/Interperiodica Publishing.