13194-69-9

Usage

Uses

Used in Pharmaceutical Industry:
2-IODO-5-METHYLANILINE is used as a key building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Dye Industry:
In the dye industry, 2-IODO-5-METHYLANILINE serves as a crucial component in the production of various dyes, enhancing color properties and performance in different applications.
Used in Agrochemical Production:
2-IODO-5-METHYLANILINE is utilized as an intermediate in the manufacturing process of agrochemicals, playing a significant role in the development of effective and safe agricultural products.
Used in Specialty Chemicals:
2-IODO-5-METHYLANILINE is also employed in the production of specialty chemicals, where its unique properties are leveraged to create high-value products for specific applications.
Safety and Handling:
Due to its potential hazards, 2-IODO-5-METHYLANILINE is typically handled and stored in a controlled environment to prevent exposure and ensure safety throughout its various applications.

InChI:InChI=1/C7H8IN/c1-5-2-3-6(8)7(9)4-5/h2-4H,9H2,1H3

Upstream product

• 142-71-2 copper diacetate 
• 64-19-7 acetic acid 
• 108-44-1 1-amino-3-methylbenzene 
• 89-62-3 4-methyl-2-nitroaniline 
• 7732-18-5 water 
• 5326-39-6 4-iodo-3-nitrotoluene 

Downstream Products

• 959698-96-5 methyl 3-[N-(2-iodo-5-methylphenyl)amino]-2,2-dimethylpropionate 
• 1038778-91-4 (2-iodo-5-methylphenyl)carbamic acid 1,1-dimethylethyl ester 
• 1094425-36-1 N,N-dimethyl-2-iodo-5-methylaniline 
• 1097819-10-7 C₁₃H₁₂BrNS 
• 66354-87-8 6-methyl-2-phenyl-1H-indole 
• 1616622-44-6 2-(5-methylbenzo[d]thiazol-2-yl)-2-phenylacetonitrile 
• 1616622-50-4 2-(5-methylbenzo[d]thiazol-2-yl)-2-(p-tolyl)acetonitrile 
• 1128-47-8 6-methylindoline-2,3-dione 
• 2523-39-9 3-methylfluorene 

Relevant academic research and scientific papers

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines

The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).

Palladium-Catalyzed Incorporation of Two C1 Building Blocks: The Reaction of Atmospheric CO2 and Isocyanides with 2-Iodoanilines Leading to the Synthesis of Quinazoline-2,4(1H,3H)-diones

A Pd-catalyzed insertion and cycloaddition of CO2 and isocyanide into 2-iodoanilines under atmospheric pressure has been developed and affords quinazoline-2,4(1H,3H)-diones through the formation of new C-C, C-O, and C-N bonds under mild conditions. This reaction provides a new and practical method not only for the construction of quinazoline-2,4(1H,3H)-diones but also for the efficient utilization of carbon dioxide.

Synthesis and structural insights of substituted 2-iodoacetanilides and 2-iodoanilines

This study reports a simple and efficient method for the direct iodination of substituted anilines with molecular iodine and copper acetate in acetic acid producing 2-iodoacetanilies and 2-iodoanilines. Employing density functional theory (B3LYP) and MidiX basis set, computational study is performed to calculate equilibrium geometries, IR vibrational frequencies, and thermodynamic properties including change of energy, enthalpy and Gibbs free energies. The optimized geometries indicated longer C-I bond distance (2.133 ?) which makes iodine slightly positive. The partial atomic charge profile and electrostatic potential further confirmed that most of the iodinated products are capable of forming a distinct halogen bonding . The thermodynamic properties disclosed that all iodination reactions are endothermic. Understanding the substituents' effect, molecular frontier orbital (MO) calculations are conducted finding the HOMO, LUMO and HOMO-LUMO gaps for all compounds. The MO calculations revealed that two electron-withdrawing iodine groups have significant influence on lowering the HOMO-LUMO gap compared to one iodine group in the products.

Silver-catalyzed incorporation of carbon dioxide into o-alkynylaniline derivatives

Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.

Palladium-catalyzed intermolecular cyclocarbonylation of 2-iodoanilines with the Michael acceptor, diethyl ethoxycarbonylbutendienoate

Palladium-catalyzed intermolecular cyclocarbonylation of 2-iodoanilines with diethyl ethoxycarbonylbutendienoate produces 2,3,3-triethoxycarbonyl-2,3- dihydro-4(1H)-quinolinone derivatives in moderate to good yields. This protocol involves Michael additio

Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks

An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate α-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright

Multicomponent cascade reactions: A novel and expedient approach to functionalized indoles by an unprecedented nucleophilic addition- heterocyclization-oxidative alkoxycarbonylation sequence

A novel multicomponent cascade process is reported, based on the sequential combination between an initial nucleophilic attack step to an imine moiety and a palladium-catalyzed oxidative heterocyclization-alkoxycarbonylation process. By this new process, five simple molecules [2-alkynylaniline imines, alcohol (ROH), carbon monoxide (CO), alcohol (ROH), and oxygen (O2)] are sequentially activated, selectively leading to high value-added functionalized indole derivatives in a single operation. Copyright

Microwave-accelerated iodination of some aromatic amines, using urea-hydrogen peroxide addition compound (UHP) as the oxidant

A fast and simple method for the oxidative iodination of some aromatic amines, under microwave irradiation, is reported, using diiodine and the the strongly H-bonded urea-hydrogen peroxide addition compound (H 2NCONH)2...H2O2, UHP) as the oxidant. The reactions were carried out in boiling CHCl3 under a reflux condenser to afford, within 10 minutes, the purified monoiodinated products in 40-80% yields.