71643-66-8

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-iodophenol is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of new drugs and enhance the properties of existing ones.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chloro-2-iodophenol is utilized as an intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Dye Production:
4-Chloro-2-iodophenol is used as a building block in the synthesis of dyes, enabling the creation of a wide range of colorants for various applications, including textiles, plastics, and printing inks.
Used in Specialty Chemicals Production:
4-Chloro-2-iodophenol is also employed in the production of specialty chemicals, where its unique properties can be leveraged to develop high-value products for specific applications in various industries.

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

Upstream product

• 533-58-4 2-Iodophenol 
• 106-48-9 4-chloro-phenol 
• 132905-91-0 Isopropyl-carbamic acid 4-chloro-phenyl ester 
• 52807-27-9 4-chloro-2-iodo-1-methoxybenzene 
• 95-85-2 2-hydroxy-5-chloro-aniline 

Downstream Products

• 2040-83-7 2,4-dichloro-6-iodophenol 
• 15459-50-4 4-chloro-2,6-diiodo-phenol 
• 183589-01-7 4-chloro-2-iodophenyl acetate 
• 71643-34-0 C₂₀H₁₃BrCl₂I₂O₃ 
• 135062-07-6 1-(3-Bromo-propoxy)-4-chloro-2-iodo-benzene 
• 253877-27-9 6-chloro-3-p-tolyl-benzo[e][1,3]oxazine-2,4-dione 
• 18655-97-5 3-(4-bromo-phenyl)-6-chloro-benzo[e][1,3]oxazine-2,4-dione 
• 18761-36-9 5-chloro-2-phenylbenzofuran 
• 100398-25-2 2-benzyloxy-5-chloroiodobenzene 
• 198902-28-2 2-(acetyloxy)-5-chlorobenzonitrile 
• 187273-03-6 3-cyano-5-chloro-2-hydroxyacetophenone 
• 187273-05-8 5-chloro-2-hydroxy-3-(5-tetrazolyl)-acetophenone 
• 187272-85-1 5'-chloro-3'-cyano-2'-hydroxy-3-[2-(2-quinolinyl)ethenyl]chalcone 

Relevant academic research and scientific papers

Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates

Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

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.

Oxyacylation of Iodoalkynes: Gold(I)-Catalyzed Expeditious Access to Benzofurans

(Acetonitrile)[1,3-bis(2,6-diisopropylphenyl)-imidazole-2-ylidene] gold(I) catalyzes the cycloisomerization of 2-(iodoethynyl)aryl esters to give 3-iodo-2-acyl benzofurans. This catalytic transformation is the result of an unprecedented selective syntheti

Oxahelicene NHC ligands in the asymmetric synthesis of nonracemic helicenes

A straightforward approach to enantiopure 2H-pyran-modified amino[5]helicenes and amino[6]helicenes was developed. They were converted to 1,3-disubstituted imidazolium salts and used as NHC ligand precursors in the Ni0-catalysed enantioselective [2+2+2] cycloisomerisation of aromatic triynes to obtain the model helicene derivatives in up to 86% ee.

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.

Isoquinolinium Dichromate and Chlorochromate as Efficient Catalysts for Oxidative Halogenation of Aromatic Compounds under Acid-Free Conditions

Isoquinolinium dichromate and isoquinolinium chlorochromate were found as efficient catalysts to trigger oxidative bromination and iodination of aromatic hydrocarbons with KBr/KI and KHSO4 under acid-free conditions. Reaction times reduced highly significantly under sonication, followed by corresponding mono bromo derivatives in very good yield with high regioselectivity.

Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol

An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.

One-pot synthesis of 2,2′-bisbenzofurans using cuprous chloride as a catalyst

A variety of novel 5,5′-disubstituted-2,2′-bisbenzofuran derivatives were synthesized by treatment of 4-substituted-2-(2- trimethylsilylethynyl)phenyl tert-butyldimethylsilyl ether analogues with CuCl as a catalyst in 62-82% isolated yields. This novel st