2012-29-5

Basic information

• Product Name: 2,4-DIIODOPHENOL
• Synonyms: 2,4-diiodo-pheno;2,4-DIIODOPHENOL;4-Iodo-2-iodophenol
• CAS NO: 2012-29-5
• Molecular Formula: C₆H₄I₂O
• Molecular Weight: 345.9
• Mol File: 2012-29-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 283.8°Cat760mmHg
• Flash Point: 125.4°C
• Appearance: /
• Density: 2.62g/cm³
• Vapor Pressure: 0.00181mmHg at 25°C
• Refractive Index: 1.753
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.90±0.18(Predicted)
• CAS DataBase Reference: 2,4-DIIODOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIIODOPHENOL(2012-29-5)
• EPA Substance Registry System: 2,4-DIIODOPHENOL(2012-29-5)

Safety Data

• Hazardous Substances Data: 2012-29-5(Hazardous Substances Data)

Usage

General Description

2,4-DIIODOPHENOL, also known as 2,4-diiodoresorcinol, is a chemical compound that belongs to the class of diiodophenols. It is a derivative of resorcinol and is characterized by having two iodine atoms attached to the benzene ring. 2,4-DIIODOPHENOL is commonly used in organic synthesis and as a chemical intermediate in the production of pharmaceuticals and dyes. It has also been studied for its potential use as a contrast agent in imaging techniques such as magnetic resonance imaging (MRI). Additionally, 2,4-DIIODOPHENOL has been investigated for its anti-cancer properties, with some studies suggesting that it may have potential as a therapeutic agent in the treatment of certain types of cancer. However, further research is needed to fully understand its biological and pharmacological activities.

InChI:InChI=1/C6H4I2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H

Upstream product

• 609-23-4 2,4,6-Triiodophenol 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 108-95-2 phenol 
• 7553-56-2 iodine 
• 6303-60-2 2,4-diiodo-1-nitro-benzene 
• 533-58-4 2-Iodophenol 
• 540-38-5 p-Iodophenol 
• 123-30-8 4-amino-phenol 
• 116529-48-7 2,6-diiodo-3-nitro-aniline 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 77-09-8 phenolphthalein 
• 533-70-0 2,4-diiodoaniline 

Downstream Products

• 77228-65-0 (2,4-diiodophenoxy)acetic acid 
• 90416-96-9 <2.4-diiod-phenoxy>-essigsaeure-methylester 
• 90917-47-8 <2.4-Diiod-phenoxy>-essigsaeure-ethylester 
• 88-89-1 2,4,6-Trinitrophenol 
• 946-31-6 2-chloro-4,6-dinitro-phenol 
• 1257216-66-2 C₁₉H₂₀INO₃S 
• 1257216-63-9 8-(4-chlorophenylthio)-1,2,3,4,4a,10,10a-heptahydro-10-tosyl-10H-phenoxazine 
• 1257216-64-0 1,2,3,4,4a,10,10a-heptahydro-8-morpholino-10-tosyl-10H-phenoxazine 
• 1257216-46-8 3,4-dihydro-6-iodo-2-phenyl-4-tosyl-2H-1,4-benzoxazine 
• 1257216-65-1 7-(pyrrolidin-1-yl)-9-tosyl-1,2,3,3a,9,9a-hexahydrobenzo[e]cyclopenta[b][1,4]oxazine 
• 1257216-67-3 C₁₈H₁₈INO₃S 

Relevant articles and documents

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ON THE PRODUCT DISTRIBUTION IN THE IODINATION OF PHENOL

The product distribution in the iodination of phenol with I2 in water solution is buffer and pH dependent with the ortho product increasing at low pH and low buffer concentration.This effect is attributed to different rates of proton transfer form the 4-iodo-2,5-; and 2-iodo-3,5-cyclohexadienone intermediate.

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.

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.