666727-31-7

Usage

Uses

Used in Chemical Industry:
2-Chloro-3-iodophenol is used as a reactive intermediate for the synthesis of various organic compounds. Its reactivity, due to the presence of halogen atoms, makes it a valuable component in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research Laboratories:
2-Chloro-3-iodophenol is used as a research chemical for studying the effects of halogenated phenols on chemical reactions and their potential applications in the development of new materials and compounds. Its reactivity and properties are of interest to researchers in the fields of organic chemistry and materials science.

InChI:InChI=1/C6H4ClIO/c7-6-4(8)2-1-3-5(6)9/h1-3,9H

Upstream product

• 863870-84-2 O-2-chloro-3-iodophenyl N,N-diethylcarbamate 
• 863870-73-9 O-3-iodophenyl N,N-diethylcarbamate 
• 626-02-8 3-Iodophenol 

Downstream Products

• 945470-04-2 2-chloro-1-iodo-3-methoxybenzene 
• 945470-05-3 1-benzyloxy-2-chloro-3-iodobenzene 
• 945470-16-6 2-chloro-1-(1-hexynyl)-3-methoxybenzene 
• 945470-18-8 1-benzyloxy-2-chloro-3-(1-hexynyl)benzene 
• 666727-33-9 2-chloro-3-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)-phenol 
• 1287791-81-4 N-(2-chloro-3-iodophenyl)-2-hydroxy-2-methylpropanamide 
• 1287791-73-4 2-(2-chloro-3-iodophenoxy)-2-methylpropanamide 

Relevant academic research and scientific papers

In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System

A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1 H-indoles

2,3-Dihaloanilines have been proved as useful starting materials for synthesizing 4-halo-1H-indoles. Subsequent or in situ functionalization of the prepared haloindoles allows the access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles in good overall yields. As no efficient synthetic routes to 2,3-dihaloanilines have been described in the literature, different approaches to the preparation of these 1,2,3-functionalized aromatic precursors are now presented. The most general one involves a Smiles rearrangement from the corresponding 2,3-dihalophenols and allows the preparation of 2,3-dihaloanilides in a straightforward and synthetically useful manner.

Regioselective synthesis of 4- and 7-alkoxyindoles from 2,3-dihalophenols: Application to the preparation of indole inhibitors of phospholipase A 2

(Chemical Equation Presented) An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been developed from commercially available starting materials such as 3-halophenols and 3-chloroanisole. Directed ortho-metalation followed by two pallad

A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols

Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzo[b]furans, which can be easily transformed into 4-functionalized benzo[b]furans, that are difficult to synthesize by other proc