1608-47-5

Usage

Uses

Used in Pharmaceutical Synthesis:
3,4-Diiodotoluene is utilized as an intermediate in the production of pharmaceuticals, contributing to the synthesis of a range of medicinal compounds due to its unique chemical properties.
Used in Dye Production:
In the dye industry, 3,4-Diiodotoluene serves as a crucial intermediate, facilitating the creation of various dyes that have specific applications in different sectors.
Used in Organic Synthesis:
As a versatile reagent, 3,4-Diiodotoluene is employed in organic synthesis for its ability to participate in a variety of chemical reactions, thus broadening its utility in research and development.
Used in Medical Imaging:
3,4-Diiodotoluene is predominantly used in the manufacturing of iodinated contrast media, which are essential for medical imaging techniques such as CT scans and X-rays. Its role in enhancing the visibility of internal structures during these procedures is invaluable for accurate diagnostics.
Used in Research Laboratories:
In research settings, 3,4-Diiodotoluene is a valuable compound for conducting experiments and exploring new chemical reactions and synthesis pathways, further expanding its applications in the scientific community.
Used in Chemical Manufacturing:
Chemical manufacturing facilities often incorporate 3,4-Diiodotoluene into their processes to produce a variety of end products, highlighting its importance in the chemical industry.

InChI:InChI=1/C7H6I2/c1-5-2-3-6(8)7(9)4-5/h2-4H,1H3

Upstream product

• 13194-69-9 2-iodo-5-methylaniline 
• 624-31-7 4-tolyl iodide 
• 139778-27-1 2-Iodo-5-methylbenzenesulfonic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 262373-15-9 4-methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 89-62-3 4-methyl-2-nitroaniline 
• 5326-39-6 4-iodo-3-nitrotoluene 

Downstream Products

• 85090-26-2 5-methyl-2-phenylisoindoline-1,3-dione 
• 40314-06-5 5-methyl-1H-isoindole-1,3-(2H)-dione 
• 165544-43-4 3-Methyl-1,2-bis(phenylethynyl)benzene 

Relevant academic research and scientific papers

Aryne Insertion into I-I σ-Bonds

A new protocol for the efficient synthesis of o-diiodoarenes has been developed. This method allows the synthesis of substituted and polycyclic o-diiodoarenes, which are difficult to obtain by classical methods. This diiodination process involves the formal insertion of arynes into the I-I σ-bond.

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.

Preparation of N-Substituted Phthalimides by Palladium-Catalyzed Carbonylation and Coupling of o-Dihalo Aromatics and Primary Amines

A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115 deg C, 90 psi of CO, 3 percent PdCl2L2, and 2.4 equiv of DBU.This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.

STOICHIOMETRIC AND CATALYTIC OXIDATIVE IODINATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS IN AQUEOUS TRIFLUOROACETIC ACID

The conditions for oxidative monoiodination of benzene, halogenobenzenes, toluene, halogenotoluenes, and p-toluic acid in solvents based on trifluoroacetic acid were studied.Yields of the respective iodoarenes close to quantitative were obtained in systems containing 10-20 vol. percent of water in the solvent with equimolar amounts of alkali-metal metal iodides in relation to the substrate in the presence of stoichiometric (under anaerobic conditions) or catalytic (in the presence of oxygen or air) amounts of alkali-metal nitrates.The analogous reactions with nitrites can only be conducted under aerobic conditions.These iodinating systems are compared with systems based on acetic acid containing iodine and mixtures of sulfuric and nitric acids.The conditions for the iodination of toluene and for the transformations of the obtained iodotoluenes in the presence of nitrogen-containing oxidizing agents in trifluoroacetic acid solutions were studied in detail.It was shown that p-iodotoluene undergoes ipso-nitrodeiodination to a significant degree under these conditions.It is supposed that the iodinating agent in the investigated systems is trifluoroacetyl hypoiodite.Data on the assignment of the PMR spectra of the synthesized isomeric nitroiodotoluenes and chloroiodotoluenes by a simple additive method are given.