41252-97-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Iodo-2-nitrotoluene is used as a synthetic intermediate for the production of 3-(4-methyl-3-nitro-phenyl)-1H-indole, which is a compound with potential applications in the pharmaceutical industry. The synthesis of this indole derivative takes place at a temperature of 40°C, highlighting the utility of 4-Iodo-2-nitrotoluene in facilitating the formation of biologically active molecules.

InChI:InChI=1/C7H6INO2/c1-5-2-3-6(8)4-7(5)9(10)11/h2-4H,1H3

Upstream product

• 624-31-7 4-tolyl iodide 
• 88-72-2 1-methyl-2-nitrobenzene 
• 7697-37-2 nitric acid 
• 106-49-0 p-toluidine 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 60956-26-5 4-bromo-2-nitrotoluene 
• 119-32-4 4-Methyl-3-nitroanilin 

Downstream Products

• 83863-33-6 5-iodo-o-toluidine 
• 116529-62-5 4-iodo-2-nitro benzoic acid 
• 28442-37-7 3,3’-dinitroditoluene 
• 59383-47-0 4-methyl-3-nitro-cinnamic acid methyl ester 
• 375792-98-6 4-iodo-1-(bromomethyl)-2-nitrobenzene 
• 450841-56-2 4-[(2-amino-4-iodobenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitrile 
• 450841-51-7 4-[(4-iodo-2-nitrobenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitrile 
• 669009-76-1 N-{2-[(4-cyanophenyl)-(3-methyl-3H-imidazol-4-yl)methoxymethyl]-5-iodophenyl}benzamide 
• 450841-59-5 thiophene-2-sulfonic acid {2-[(4-cyanophenyl)-(3-methyl-3H-imidazol-4-yl)methoxymethyl]-5-iodophenyl}amide 
• 669009-71-6 N-{2-[(4-cyano-phenyl)-(3-methyl-3H-imidazol-4-yl)-methoxymethyl]-5-iodo-phenyl}-4-methyl-benzenesulfonamide 
• 669009-75-0 4-[[2-(3,5-difluorobenzylamino)-4-iodobenzyloxy]-(3-methyl-3H-imidazol-4-yl)methyl]benzonitrile 

Relevant academic research and scientific papers

Novel functionalized indigo derivatives for organic electronics

A series of nine novel indigo derivatives, including diiodoindigo, octahalogenated indigoids and compounds with extended π-conjugated system, were synthesized, characterized and investigated as semiconductor materials in organic field-effect transistors (OFETs). Among them, 6,6′-diiodoindigo demonstrated the ambipolar behavior with balanced p-type and n-type mobilities. The complete substitution of hydrogens at the indigo core with halogen atoms led to low electron mobilities in OFETs. An extension of the conjugated system through the introduction of small aromatic substituents (thiophene and phenyl) resulted in predominant p-type behavior. Fusion of aromatic rings resulted in z-shaped dibenzoindigo, which showed poor charge transport properties due to the non-optimal arrangement of molecules along each other in the crystal lattice. The acquired data fulfilled the previously reported model based on the relationship between the chemical nature of substituents and their positions at the indigo core, optoelectronic properties of materials and their performance in OFETs. The results of this study will be useful for rational design of a new generation of the indigo-based semiconductors for biocompatible organic electronics.

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.

Diastereoselective Total Synthesis of Raputindole A

The first diastereoselective total synthesis of the bisindole alkaloid raputindole A is reported. After Au(I)-catalyzed assembly of the cyclopenta[f]indole tricycle, it was possible to hydrogenate the indene double bond regio- A nd diastereoselectively through iridium catalysis, guided by a preinstalled hydroxy function. Attempted HWE reaction led to formal elimination of formaldehyde from an α-quaternary cyclopentane carbaldehyde, which was circumvented by Takai olefination. After Suzuki-Miyaura cross coupling and deprotection/oxidation, (±)-raputindole A was obtained in 13 linear steps in 18% overall yield.

N-Iodosuccinimide (NIS) in Direct Aromatic Iodination

N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.

Method for synthesizing m-iodonitrobenzene compound

Provided is a method for synthesizing m-iodonitrobenzene; in the presence of oxygen gas, a palladium catalyst, a copper additive, a bismuth reagent and potassium phosphate, an o-nitrobenzoic acid compound and metal iodide are subjected to a substitution reaction in an organic solvent to form a corresponding m-iodonitrobenzene compound, wherein a metal in the metal iodide is an alkali metal or an alkaline earth metal. The method has obvious advantages of cheap and easily obtained reaction raw materials (including o-nitrobenzoic acid and MI), small amount of the metal catalyst, minimum environmental pollution with oxygen gas as an oxidant, good tolerance on various functional groups on an aromatic ring and the like. The method can be widely applied in the fields of synthesis of drugs, materials, natural products and the like in industrial and academic circles.

Total Synthesis and Absolute Configuration of Raputindole A

The first total synthesis of the bisindole alkaloid raputindole A from the rutaceous plant Raputia simulans is reported. The key step is a Au(I)-catalyzed cyclization that assembles the cyclopenta[f]indole tricycle from a 6-alkynylated indoline precursor. The isobutenyl side chain was installed by Suzuki-Miyaura cross-coupling, followed by a regioselective reduction employing LiDBB. Starting from 6-iodoindole, the sequence needs nine steps and provided (±)-raputindole A in 6.6% overall yield. The absolute configuration of the natural product (+)-raputindole A was determined by quantum chemical calculation of the ECD spectrum.

Nucleotides and nucleosides and methods for their use in DNA sequencing

The present invention relates generally to labeled and unlabled cleavable terminating groups and methods for DNA sequencing and other types of DNA analysis. More particularly, the invention relates in part to nucleotides and nucleosides with chemically cleavable, photocleavable, enzymatically cleavable, or non-photocleavable groups and methods for their use in DNA sequencing and its application in biomedical research.

SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).

Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems

Iodination of o-nitrotoluene in H2SO4 or CF 3SO3H at 0°C with compounds having a nitrogen-iodine bond leads to the formation of isomeric mono- and diiodo derivatives whose ratio differs from the statistical value. The reaction of nitrobenzene with 2 equiv of N-I reagents in trifluoromethanesulfonic acid at 0°C takes less than 1 min and yields 79-85% of m-iodonitrobenzene. The electrophilic reactivity of the iodinating agents was estimated by quantum-chemical methods.