612-55-5

Usage

Uses

Used in Chemical Synthesis:
2-Iodonaphthalene is used as a reagent in chemical synthesis for producing new molecules. Its unique reactivity allows for the creation of a wide range of compounds, making it a valuable resource in research and development.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2-Iodonaphthalene is used as an intermediate in the synthesis of various drugs. Its ability to undergo chemical transformations makes it a useful component in the development of new medications.
Used in Material Sciences:
2-Iodonaphthalene is also utilized in material sciences for the synthesis of novel materials with specific properties. Its reactivity contributes to the creation of materials with potential applications in various fields.
Safety Measures:
As with many chemicals, handling 2-Iodonaphthalene requires specific safety measures. It may cause skin and eye irritation, and could be harmful if swallowed. Proper precautions should be taken to minimize exposure and ensure safe handling.

InChI:InChI=1/C10H7I/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

Upstream product

• 91-20-3 naphthalene 
• 30389-02-7 2-iodonaphthalene - picric acid complex 
• 109942-04-3 2-dichloroiodanyl-naphthalene 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 38846-64-9 2-ethynylbenzaldehyde 
• 78-82-0 Isobutyronitrile 
• 32316-92-0 naphthalene-2-boronic acid 
• 110-59-8 pentanonitrile 

Downstream Products

• 62062-39-9 1-naphthalen-1-yl-piperidine 
• 5465-85-0 N-(2-naphthyl)piperidine 
• 612-78-2 2,2'-binaphthalene 
• 5693-33-4 2-(naphthalen-2-yl)benzoic acid 
• 32316-92-0 naphthalene-2-boronic acid 
• 4325-74-0 1-(naphthalen-2-yl)naphthalene 
• 73178-12-8 C₁₇H₁₅IO₄S 
• 91-57-6 2-Methylnaphthalene 
• 93-09-4 naphthalene-2-carboxylate 
• 91-20-3 naphthalene 
• 613-81-0 bis(2-naphthyl)sulfide 
• 85052-78-4 C₂₂H₁₈S₂ 
• 23975-17-9 2-phenylethynyl-naphthalene 
• 82408-29-5 phenyl naphthalene-2-carboxylate 

Relevant academic research and scientific papers

The Oxyiodination of Aromatic Compounds over Zeolite KX: The Case of Naphthalene

Aromatic compounds, iodine, and oxygen react in the vapor phase over basic faujasite zeolites at 225-350 deg C to produce iodoaromatic compounds and water.When the aromatic compond is naphthalene and the reaction is conducted in the region of 250 deg C over KX zeolite, a shape-selective catalytic oxyiodination occurs, resulting in predominant iodination at the 2-position of naphthalene.Typical product mixtures contain approximately 10percent 1-iodonaphthalene, 65percent 2-iodonaphthalene, 19percent 2,6-diiodonaphthalene, 5percent other diiodonaphthalene isomers, and 1percent mixed triiodonaphthalene isomers at approximately 20percent naphthalene conversion and 80-99percent iodine conversion.Excessive conversion and excessive residence time reduce the selectivity to kinetic product, 2,6-diiodonaphthalene, but do not alter the selectivity for iodination in the 2-position.Selectivity for iodination in the 2-position is decreased by substituting sodium for potassium in the zeolite, by alterning the faujasite zeolite Si/Al ratio significantly above or below 1.25 and by increasing the amount of iodine in the reactant feed.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Cu-Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO

The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system (TEMPO=2,2,6,6-tetramethylpiperidine N-oxide). The broad substrate scope includes a variety of electron-rich and electron-poor arylboronic acids, which react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent, and shows high reactivity for the formation of the CN- moiety. Moreover, TEMPO acts as a cheap oxidant to enable the reaction to be catalytic in copper. The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system. Electron-rich and electron-poor arylboronic acids react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent. Moreover, TEMPO, a cheap oxidant, enables the reaction to be catalytic in copper (see scheme; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide).

Photochemical generation and reactivity of naphthyl cations: cine substitution

The photochemical solvolyses of naphthalen-1-yl(phenyl)-iodonium tetrafluoroborate and naphthalen-2-yl(phenyl)-iodonium tetrafluoroborate in methanol regiospecifically yield the naphthalen-1- and -2-yl ethers but afford scrambled 1- and 2-phenylnaphthalene Friedel-Crafts products. It is demonstrated that singlet naphthyl cations account for the formation of the naphthyl ethers, but that the cine substitution is most likely to be due to the intermediacy of triplet naphthyl cations. According to the experiments reported here, the singlet naphthyl cations are lower in energy than their triplet isomers. High-level MO calculations for the cations in methanol support this finding. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Comparative study of the reactivity of iodinating agents in solution and solid phase

The results of reactions of a series of aromatic substrates with iodine, iodine(I) chloride, and N-iodosuccinimide in solution and solid phase were compared for the first time. In all cases, the general relations holding in the iodination process were similar. Iodine(I) chloride was found to chlorinate anthracene. A high efficiency of solid-phase iodination of β-diketones was demonstrated using dibenzoylmethane as an example.

A Computerised Least Square Method for Determination of Stability Constants of 1:1 Molecular Complexes and Chemical Shift of Pure Complexes from Nuclear Magnetic Resonance Data

A computerised method utilising nuclear magnetic resonance data has been developed for the determination of stability constants of 1:1 molecular complexes.It is based on the principle of least squares in which the coefficients are adjusted under a constraint with the help of Lagrange's method of undetermined multipliers.The method utilises the complete expression for equilibrium constant and is mathematically rigorous, straightforward, non-iterative and requires very little computer time.