609-23-4

Basic information

• Product Name: 2,4,6-Triiodophenol
• Synonyms: 2,4,6-Trijodfenol;bobel24;Phenol, 2,4,6-triiodo-;2,4,6-Triiodophenol, 98+%;2,4,6-Triiodophenol;2,4,6-Triiodophenol 97%
• CAS NO: 609-23-4
• Molecular Formula: C₆H₃I₃O
• Molecular Weight: 471.8
• EINECS: 210-186-7
• Product Categories: Aromatic Phenols;Iodine Compounds;Phenols;Organic Building Blocks;Oxygen Compounds
• Mol File: 609-23-4.mol

Chemical Properties

• Melting Point: 157-159 °C(lit.)
• Boiling Point: 316.3 °C at 760 mmHg
• Flash Point: 145.1 °C
• Appearance: GREY TO TAN TO BROWN POWDER
• Density: 2.8493 (estimate)
• Vapor Pressure: 0.000224mmHg at 25°C
• Refractive Index: 1.816
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 6.47±0.23(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 2046861
• CAS DataBase Reference: 2,4,6-Triiodophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Triiodophenol(609-23-4)
• EPA Substance Registry System: 2,4,6-Triiodophenol(609-23-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-20/21
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: SN2800000
• TSCA: Yes
• Hazardous Substances Data: 609-23-4(Hazardous Substances Data)

Usage

Uses

Used in Water Treatment Industry:
2,4,6-Triiodophenol is used as an iodinated disinfection byproduct formed during the chlorination of sewage effluents. Its formation is a result of the reaction between iodide ions and the oxidizing agents used in the chlorination process, contributing to the overall disinfection efficacy of the treated water.
Used in Environmental Research:
2,4,6-Triiodophenol is used as a potent thyroid disrupting chemical in environmental research. Its ability to interfere with thyroid hormone function makes it a valuable tool for studying the effects of endocrine-disrupting chemicals on aquatic organisms and ecosystems.
Used in Biochemical Studies:
2,4,6-Triiodophenol is utilized in biochemical studies to investigate deiodinase enzymes. These enzymes play a crucial role in the regulation of thyroid hormone metabolism, and the use of 2,4,6-triiodophenol as a substrate allows researchers to better understand the mechanisms and functions of deiodinase enzymes in various biological processes.

InChI:InChI=1/C6H3I3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H

Upstream product

• 119-30-2 2-hydroxy-5-iodobenzoic acid 
• 618-76-8 3,5-diiodo-4-hydroxybenzoic acid 
• 133-91-5 3,5-diiodosalicylic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 90-02-8 salicylaldehyde 
• 69-72-7 salicylic acid 
• 108-95-2 phenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 77-09-8 phenolphthalein 
• 64-19-7 acetic acid 
• 7553-56-2 iodine 
• 7732-18-5 water 
• 7790-99-0 Iodine monochloride 
• 56-23-5 tetrachloromethane 

Downstream Products

• 98554-64-4 2,4,6-triiodo-phenetole 
• 554-24-5 2-(2,4,6-triiodo-phenoxy)-butyric acid 
• 98589-36-7 2-(2,4,6-triiodo-phenoxy)-propionic acid 
• 102006-83-7 meso-2,5-bis-(2,4,6-triiodo-phenoxy)-adipic acid dimethyl ester 
• 102006-83-7 racem.-2,5-bis-(2,4,6-triiodo-phenoxy)-adipic acid dimethyl ester 
• 102747-50-2 meso-2,9-bis-(2,4,6-triiodo-phenoxy)-decanedioic acid dimethyl ester 
• 2012-29-5 2,4-diiodophenol 
• 608-71-9 Pentabromophenol 
• 20389-01-9 2,6-diiodo-p-benzoquinone 
• 20244-55-7 2,4,4,6-tetrachlorocyclohexa-2,5-dien-1-one 
• 305-85-1 2,6-diiodo-4-nitrophenol 
• 20294-48-8 diiodo-4,6 nitro-2 phenol 
• 118-75-2 chloranil 

Relevant articles and documents

Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C?H Halogenation

A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C?H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur

One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides

This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.

Oxidative azidations of phenols and ketones using iodine azide after release from an ion exchange resin

The oxidative oligoazidation of phenols and ketones using iodine azide (IN3) provided by its release from an ion exchange resin is reported. Preliminary mechanistic studies indicate a previously unknown reactivity of iodine azide toward phenols and ketones.

Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.

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.

Synthesis of (-)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation

A 1,4-addition strategy using an enone and a copper reagent was studied for the synthesis of (-)-piperitylmagnolol. A MOM-protected biphenol copper reagent was added to BF3·OEt2-activated 4-isopropylcyclohexenone, whereas 1,4-addition of protected monophenol reagents possessing an allyl group was found to be unsuccessful. The allyl group was later attached to the p-,p′-diiodo-biphenol ring by Pd-catalyzed coupling with allylborate. The aforementioned iodide was synthesized using a new method for ortho-selective deiodination of o-,p-diiodophenols.

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

Fast halogenation of some N-heterocycles by means of N,N'-dihalo-5,5- dimethylhydantoin

An instantaneous, selective and high-yielding halogenation process is reported. The method operates with imidazoles, pyrazoles, and indoles under benign reaction conditions. The developed process involves the use of N,N'-dihalo-5,5-dimethylhydantoins (halo=chlorine, bromine, iodine) as halogenation reagents that are activated by catalytic quantities of a strong Bronsted acid. Moreover, the halogenation process is switchable to produce either the mono- or di-halogenated products. Issues related to the reaction mechanism are investigated and a proposal for a reaction mechanism is disclosed.

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.

Gas-Chromatographic identifi cation of products formed in iodination of methyl phenols by retention indices

Iodination reaction followed by conversion of iodine-substituted methylphenols to the corresponding trifl uoroacetates was suggested for improving the sensitivity of the gas-chromatographic determination of phenol and its methyl-substituted derivatives (al isomers of mono- and diethylphenols, 2,3,5-, 2,3,6-, and 3,4,5-trimethylphenols) in aqueous media. Acylation products of iodo methylphenols (104 compounds) were identifi ed by linear-logarithmic retention indices on a standard nonpolar polydimethylsiloxane stationary phase, and the pattern of their variation with the number and nature of substituents were characterized. A procedure for identifi cation of methyl-substituted phenols in water in their gas-chromatographic determination with an electron-capture detector was developed. Pleiades Publishing, Ltd., 2012.