25309-64-2

Usage

Chemical Properties

clear colorless to yellow liquid

InChI:InChI=1/C8H9I/c1-2-7-3-5-8(9)6-4-7/h3-6H,2H2,1H3

Upstream product

• 100-41-4 ethylbenzene 
• 7553-56-2 iodine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 110-00-9 furan 
• 589-16-2 4-aminoethylbenzene 
• 2351-50-0 4-iodostyrene 
• 98-69-1 p-ethylbenzenesulfonic acid 
• 63139-21-9 4-ethylphenylboronic acid 
• 90086-41-2 1-(4-iodophenyl)ethan-1-amine 
• 96979-73-6 (cyclo-C₆H₁₁)3SnC₆H₄-p-C₂H₅ 
• 96227-75-7 (4-Ethyl-phenyl)-piperidin-1-yl-diazene 
• 13329-40-3 4-Iodoacetophenone 

Downstream Products

• 29778-20-9 1-ethyl-4-(phenylethynyl)benzene 
• 86897-10-1 1,2-dibromo-1-(p-iodophenyl)ethane 
• 79135-69-6 1-ethyl-4-[2-(4-ethylphenyl)-1-ethynyl]benzene 
• 186494-22-4 Bis-(4-ethyl-phenyl)-(3-nitro-phenyl)-amine 
• 619-58-9 4-iodobenzoic acid 
• 13049-40-6 4,4'-diethylbiphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 58244-47-6 4-ethyl-4'-methoxy-1,1'-biphenyl 
• 100-66-3 methoxybenzene 
• 22692-80-4 1-ethyl-4-(p-tolylethynyl)benzene 
• 918625-92-0 3-(4-ethylphenyl)-prop-2-yn-1-ol 
• 835882-20-7 (2-amino-5-chloro-phenyl)-(4-ethyl-phenyl)-methanone 

Relevant academic research and scientific papers

Reductive Deamination with Hydrosilanes Catalyzed by B(C6F5)3

The strong boron Lewis acid tris(pentafluorophenyl)borane B(C6F5)3 is known to catalyze the dehydrogenative coupling of certain amines and hydrosilanes at elevated temperatures. At higher temperature, the dehydrogenation pathway competes with cleavage of the C?N bond and defunctionalization is obtained. This can be turned into a useful methodology for the transition-metal-free reductive deamination of a broad range of amines as well as heterocumulenes such as an isocyanate and an isothiocyanate.

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides

A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.

Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition

An efficient and rapid method has been found for the iodination of aromatic compounds using iodine and polymer-supported periodic acid (PSPIA) as an oxidant under mild aprotic conditions. The reagent after the completion of the reaction was easily removed by filtration and was regenerated for further use. This method has some advantages such as: mild reaction conditions, straight forward procedure, inexpensive method, high yields and one-pot conversion.

InBr3-catalyzed reduction of ketones with a hydrosilane: Deoxygenation of aromatic ketones and selective synthesis of secondary alcohols and symmetrical ethers from aliphatic ketones

An InBr3-Et3SiH reducing system was developed to selectively convert aliphatic ketones to a variety of secondary alcohols in moderate to good yields. An initial mixing of InBr3 and PhSiH 3 was followed by the addition of aliphatic ketones and a solvent to afford the symmetrical ether derivatives.

Synthesis of oxygen- and sulfur-bridged dirhodium complexes and their use as catalysts in the chemoselective hydrogenation of alkenes

Oxygen-bridged and sulfur-bridged rhodium homobimetallic complexes were synthesized as air-stable crystals by using 2,6-bis(phosphanylmethyl)phenolate and -thiophenolate as the ligands, respectively. The oxygen-bridged dirhodium complex has a symmetrical structure where the carbon atom at the ipso position, oxygen, and two rhodium atoms are located in the same plane. It is thermally stable compared to the sulfur-bridged dirhodium complex and shows catalytic activity for hydrogenation of alkenes with high chemoselectivity.

METHOD OF PRODUCING IODIZING AGENT, AND METHOD OF PRODUCING AROMATIC IODINE COMPOUND

A method of the present invention, for producing an iodizing agent, includes the step of electrolyzing iodine molecules in a solution by using an acid as a supporting electrolyte. This realizes (i) a method of producing an iodine cation suitable for use as an iodizing agent that does not require a sophisticated separation operation after iodizing reaction is completed, and (ii) an electrolyte used in the method. Further, a method of the present invention, for producing an aromatic iodine compound, includes the step of causing an iodizing agent, and an aromatic compound whose nucleus has one or more substituent groups and two or more hydrogen atoms, to react with each other under the presence of a certain ether compound. This realizes such a method of producing an aromatic iodine compound that position selectivity in iodizing reaction of an aromatic compound is improved.

Desulfonyloxyiodination of arenesulfonic acids with mCPBA and molecular iodine

Treatment of p-alkylbenzenesulfonic acids with mCPBA and molecular iodine gave p-alkyliodobenzenes in good to moderate yields via electrophilic ipso-substitution by the iodonium species (I+) formed. This desulfonyloxyiodination was promoted by the addition of a catalytic amount of iodoarenes, such as o-iodobenzoic acid. The same treatment of dimethylbenzenesulfonic acids and trimethylbenzenesulfonic acids with mCPBA and molecular iodine proceeded smoothly both in the absence and in the presence of o-iodobenzoic acid to provide the corresponding monoiodo-dimethylbenzene and diiodo-dimethylbenzene, and diiodo-trimethylbenzene and triiodo- trimethylbenzene, in good to moderate yields, respectively. On the other hand, the same desulfonyloxyiodination of benzenesulfonic acid and p-chlorobenzenesulfonic acid with mCPBA and molecular iodine proceeded only in the presence of o-iodobenzoic acid to generate iodobenzene and p-chloroiodobenzene, respectively, in moderate yields.

Practical electrochemical iodination of aromatic compounds

A practical method for electrochemical iodination of aromatic compounds was developed. The method involves the generation of I+ by electrochemical oxidation of I2 in CH3CN using H 2SO4 as supporting electrolyte followed by the reaction with aromatic compounds. The para/ortho selectivity for the reaction of mono-substituted benzenes was significantly improved using dimethoxyethane as cosolvent in the second step. The reaction with highly reactive aromatic compounds led to the formation of significant amounts of diiodo compounds in a macrobatch reactor. This problem was solved by fast 1:1 mixing of I+ with an aromatic compound using a microflow system consisting of a T-shaped micromixer and a microtube reactor.

Synthesis, Solubility, and Reaction of Long Alkyl-Chained Hypervalent Iodine Benzyne Precursors

Long-chained hypervalent iodine benzyne precursors bearing ethyl, butyl, hexyl, octyl, decyl, dodecyl, and tetradecyl groups were synthesized, respectively. As the alkyl chain of the benzyne precursors is lengthened, the solubility in nonpolar organic solvents and the yield of the benzyne adduct with furan gradually increases.

Zinc(II) promoted conversion of aryltriazenes to aryl iodides and aryl nitriles

Aryltriazenes react with zinc perchlorate/zinc cyanide to produces arylnitriles and react with zinc iodide to produce aryliodides. The reaction mechanism involves aryl radicals that have been trapped by addition to propenenitriles in a good preparative Meerwein arylation process.