116130-33-7

Basic information

• Product Name: 2-Chloro-4-iodophenol
• Synonyms: 2-Chloro-4-iodophenol;4-iodo-2-chlolophenol
• CAS NO: 116130-33-7
• Molecular Formula: C₆H₄ClIO
• Molecular Weight: 254.45283
• Mol File: 116130-33-7.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-Chloro-4-iodophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-iodophenol(116130-33-7)
• EPA Substance Registry System: 2-Chloro-4-iodophenol(116130-33-7)

Safety Data

• Hazardous Substances Data: 116130-33-7(Hazardous Substances Data)

Usage

General Description

2-Chloro-4-iodophenol, also known as 4-iodo-2-chlorophenol, is a chemical compound with the molecular formula C6H4ClIO. It is a white to light-brown crystalline solid that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2-Chloro-4-iodophenol is also used in the production of dyes and pigments, as well as in the manufacture of various organic compounds. 2-Chloro-4-iodophenol is considered to be a hazardous substance and should be handled with caution due to its toxic and irritant properties. It is important to follow proper safety protocols when working with this compound to minimize the risk of exposure.

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

Upstream product

• 3964-52-1 2-chloro 4-aminophenol 
• 95-57-8 2-monochlorophenol 
• 540-38-5 p-Iodophenol 

Downstream Products

• 946-31-6 2-chloro-4,6-dinitro-phenol 
• 112291-44-8 1-(benzyloxy)-2-chloro-4-iodobenzene 
• 112291-45-9 allyl-(2-chloro-4-iodo-phenyl)-ether 
• 75676-72-1 2-chloro-4-iodo-1-methoxybenzene 
• 135062-08-7 1-(3-Bromo-propoxy)-2-chloro-4-iodo-benzene 
• 95-57-8 2-monochlorophenol 
• 913171-33-2 [3-(2-chloro-4-iodo-phenoxy)-propyl]-dimethyl-amine 
• 913172-13-1 [3-(2-chloro-4-iodo-phenoxy)-propyl]-carbamic acid tert-butyl ester 
• 31599-54-9 2-chloro-4-dichloroiodanyl-anisole 
• 30220-23-6 2-Chlor-4-diacetoxyiod-anisol 
• 23383-04-2 (Dibenzoylmethan)-(3-chlor-4-methoxyphenyl)-iodonium-betain 
• 21134-11-2 Dimedon-(3-chlor-4-methoxy-phenyl)-iodonium-betain 
• 913171-88-7 (E)-3-[3-Chloro-4-(3-dimethylamino-propoxy)-phenyl]-acrylic acid methyl ester 
• 913171-91-2 (E)-3-[3-Chloro-4-(3-dimethylamino-propoxy)-phenyl]-acrylic acid 

Relevant articles and documents

Mono-selective β-C-H arylation of: N -methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group

2-(Methylthio)aniline (MTA) directed C(sp3)-H functionalisations are efficient and straightforward protocols for the selective β-modification of N-methylated amino acids. The decreased reactivity of MTA in comparison with the 8-aminoquinoline (AQ) directing group allows for selective monoarylations in high yields without the formation of side products. The protocol is also suitable for the introduction of highly functionalised side chains onto the C-terminal alanines of dipeptides. The MTA directing group can easily be removed, providing free carboxylic acids as valuable building blocks.

A quantitative structure-reactivity assessment of phenols by investigation of rapid iodination kinetics using hydrodynamic voltammetry: Applicability of the Hammett equation in aqueous medium

Halogenations of aromatic substrates in aqueous medium are essentially electrophilic substitutions proceeding at rates concomitant with the nature of the substrates and substituent motifs. Kinetics as an investigatory tool for the quantitative assessment of the structure-reactivity correlation in these reactions for a diverse range of substrates has rarely been reported, presumably due to the rapidity of these reactions in aqueous medium. We have used hydrodynamic voltammetry to investigate the rapid kinetics of uncatalyzed iodination of phenol and eight substituted phenols by iodine monochloride at constant pH in aqueous medium. The Arrhenius plots for these reactions yield comprehensive kinetic and thermodynamic data. The quantitative structure-reactivity correlation stemming from the regio- and stereospecificity of the substituent motifs on the substrates has been examined through the Hammett plot, which shows a negative slope of 1.87. The magnitudes of the rate constants, energies of activation, frequency factors, and entropy change obtained for the nine fast reactions reported, reflect the relative ease of the reaction dynamics in quantitative terms thereby ascertaining the relative reactivities of the phenols studied herein.

C-H Functionalization of N-Methylated Amino Acids and Peptides as Tool in Natural Product Synthesis: Synthesis of Abyssenine A and Mucronine e

N-Methylated amino acids and peptides with an 8-aminoquinoline (AQ) directing group can be subjected to stereoselective Pd-catalyzed β-functionalizations. The best results are obtained with aryl iodides, but alkyl and alkenyl side chains can also be introduced. The AQ protecting group can easily be removed, providing the free carboxylic acid, which can be used directly in peptide couplings. This protocol was used successfully as a key step in the synthesis of the cyclopeptide alkaloids abyssenine A and mucronine E.

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.