24154-37-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4,6-TRIIODO-PHENYLAMINE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to introduce iodine atoms into organic molecules, which can enhance the therapeutic properties of the resulting compounds.
Used in Dye Production:
In the dye industry, 2,4,6-TRIIODO-PHENYLAMINE serves as a crucial component in the production of dyes, capitalizing on its chemical structure to create a range of colors and properties in the final products.
Used in Organic Chemistry as a Reagent:
2,4,6-TRIIODO-PHENYLAMINE is employed as a reagent in organic chemistry to introduce iodine atoms into other organic molecules, facilitating the creation of new compounds with specific characteristics.
Used in Medicinal Chemistry:
Due to its unique structure and properties, 2,4,6-TRIIODO-PHENYLAMINE has potential applications in medicinal chemistry, where it can be used to develop new drugs or improve the efficacy of existing ones. However, its use in this field requires careful consideration of its toxic nature and must be conducted in a controlled laboratory setting.

InChI:InChI=1/C6H4I3N/c7-3-1-4(8)6(10)5(9)2-3/h1-2H,10H2

Upstream product

• 89-52-1 o-acetylamino-benzoic acid 
• 7790-99-0 Iodine monochloride 
• 62-53-3 aniline 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 615-43-0 2-iodophenylamine 
• 540-37-4 p-aminoiodobenzene 
• 10034-85-2 hydrogen iodide 
• 64448-33-5 nitro-benzene; compound with aluminium chloride 

Downstream Products

• 121406-54-0 2,4,6-triiodo-N,N-dimethyl-aniline 
• 89976-34-1 acetic acid-(2,4,6-triiodo-anilide) 
• 1203-92-5 2.4.6-Trijod-1-dimethylaminomethylenamino-benzol 
• 147-82-0 2,4,6-tribromoaniline 
• 634-92-4 1,2,3,5-tetraiodobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 380346-57-6 chloroacetyl-(2,4,6-triiodoaniline) 
• 409316-94-5 2,4,6-triiodo-phenyl isocyanate 
• 861550-57-4 2-bromo-1,3,5-triiodo-benzene 
• 57830-61-2 2-chloro-1,3,5-triiodo-benzene 
• 626-44-8 1,3,5-Triiodobenzene 
• 1347748-58-6 C₃₆H₁₉NO₁₂ 
• 1369583-36-7 2,4,6-triethynylbenzenamine 

Relevant academic research and scientific papers

Synthesis of diiodo- and triiodoanilines by iodination of aniline with potassium dichloroiodate and preparation of 1,3,5-triiodobenzene

A new chemoselective procedure was developed for the synthesis of 2,4,6-triiodoaniline and 2,4-diiodoaniline by the reaction of aniline with potassium dichloroiodate in dilute HCl. Subsequent deamination of 2,4,6-triiodoaniline afforded 1,3,5-triiodobenzene in good yield.

9 - Azabicyclo [3.3.1] nonane coupling [...] compound and its preparation method and use thereof (by machine translation)

The invention discloses a 9 - azabicyclo [3.3.1] nonane coupling [...] compound, its preparation method comprises the following steps: in the organic solvent, the 9 - nitrogen (6' - amino) oneself amidogen - 9 - 9 - azabicyclo [3.3.1] nonane - 3 α - alkyl amino formic acid benzene and chloro acetyl three iodo aniline derivatives in accordance with the 1: 1.0 - 1.5 molar ratio, for the catalysis of cesium hydroxide at room temperature reaction in the 20 - 30 the H, obtained as the product of the 9 - azabicyclo [3.3.1] nonane coupling [...] compound. The invention also discloses the use thereof: a contrast agent for early diagnosis of breast cancer. (by machine translation)

Iodination of industrially important aromatic compounds with aqueous potassium triiodide

A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.

Ultrasound-promoted rapid and efficient iodination of aromatic and heteroaromatic compounds in the presence of iodine and hydrogen peroxide in water

A rapid and efficient ultrasound-promoted protocol for iodination of aromatic and heteroaromatic compounds, using molecular iodine in the presence of aqueous hydrogen peroxide in water without any cosolvent, has produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in short reaction times and good to excellent yields. Copyright

Polyfluorinated functionalized m-terphenyls. New substituents and ligands in organometallic synthesis

The synthesis and structural characterization of polyfluorinated arenes 2,4,6-(C6F5)3C6H2X and 2,6-(C6F5)2-4-BrC6H2X (X = NO2, Cl, Br) obtained in the Ullmann-type cross coupling reaction is reported. The nitro derivatives were reduced to the aromatic amines. The α-diimine [2,4,6-(C6F5)3C 6H2NCMe]2 and 2,4,6-(C6F 5)3C6H2I were obtained in condensation and Sandmeyer reactions, respectively, from the corresponding amine. The syntheses of 2,4,6-(C6F5)3C 6H2NHC(O)H, 2,4,6-(C6F5) 3C6H2NC, and 2,4,6-(C6F 5)3C6H2Si(X)Me2 (X = H, F, Cl) are also described.

A mild and convenient synthesis of 1,2,3-triiodoarenes via consecutive iodination/diazotization/iodination strategy

A mild and convenient synthesis of 1,2,3-triiodoarenes has been developed. This method consists of two steps which can be performed on multigram scale with moderate to excellent yields. This report discloses a practical synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, operationally simple, scalable, and is easy to workup and to purify. We also report the first regioselective transmetalation reaction of 1,2,3-triiodoarenes to provide ortho-diiodoaryl derivatives, which are useful building blocks and indeed are hard to make by other means. CSIRO 2013.

Efficient and eco-friendly synthesis of iodinated aromatic building blocks promoted by iodine and hydrogen peroxide in water: A mechanistic investigation by mass spectrometry

The reaction of aromatic and heteroaromatic compounds with molecular iodine in the presence of aqueous hydrogen peroxide using water without any co-solvent at 50 °C for 24 h produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in very good yields. In addition, a mechanistic investigation for the iodination process was carried out by mass spectrometry.

IBX-I2 redox couple for facile generation of IOH and I +: Expedient protocol for iodohydroxylation of olefins and iodination of aromatics

(Chemical Equation Presented) IBX is readily reduced to IBAin the presence of molecular iodine in DMSO to generate hypoiodous acid (IOH), which reacts with a variety of olefins as well as R, β-unsaturated ketones leading to their respective iodohydrins with anti stereochemistry. The same redox chemistry in acetonitrile containing TFA produces iodonium ions for facile iodination of a variety of aromatic compounds in respectable isolated yields.

1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds

1,3-Diiodo-5,5-dimethylhydantoin in organic solvents successfully iodinates alkylbenzenes, aromatic amines, and phenyl ethers. The reactivity of electrophilic iodine is controlled by acidity of the medium. Superelectrophilic iodine generated upon dissolution of 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid readily reacts with electron-deficient arenes at 0 to 20°C with formation of the corresponding iodo derivatives in good yields. The structure of electrophilic iodine species generated from 1,3-diiodo-5,5- dimethylhydantoin in sulfuric acid is discussed.

Syntheses and Spectral Properties of Several Branched-chain Polyphenyls containing 1,3,5-Trisubstituted Ring(s)

Six polyphenyls, including four new compounds, 5',5''-di(2-biphenylyl)-2,2'''-diphenyl-m-quaterphenyl (3), 2,5',2''-triphenyl-m-terphenyl (4), 3,5-di(2-biphenylyl)-o-terphenyl (5), and 5''-(3-biphenylyl)-m-quinquephenyl (6), were synthesized by the Ullmann coupling reaction of iodo compounds.Proton magnetic resonance spectral studies indicated that the characteristic spectral features of the polyphenyls containing 1,3,5-trisubstituted ring system(s) were fully compatible with their conformational aspects deduced from stereomodels.Ultraviolet spectral data indicated that the dihedral angle of the pivot bond of the branched ring in the polyphenyls in solution is very similar to that of biphenyl.Keywords - Ullmann reaction; quinquephenyl; sexiphenyl; septiphenyl; decaphenyl; polyphenyl; IR; UV; 1H-NMR