133921-27-4

Basic information

• Product Name: 4-IODO-3-METHYL-PHENOL
• Synonyms: 4-IODO-3-METHYL-PHENOL;3-methyl-4-iodophenol
• CAS NO: 133921-27-4
• Molecular Formula: C₇H₇IO
• Molecular Weight: 234.03435
• Mol File: 133921-27-4.mol

Chemical Properties

• Boiling Point: 276.673°C at 760 mmHg
• Flash Point: 121.128°C
• Appearance: /
• Density: 1.854g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.46±0.18(Predicted)
• CAS DataBase Reference: 4-IODO-3-METHYL-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODO-3-METHYL-PHENOL(133921-27-4)
• EPA Substance Registry System: 4-IODO-3-METHYL-PHENOL(133921-27-4)

Safety Data

• Hazardous Substances Data: 133921-27-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-IODO-3-METHYL-PHENOL is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
4-IODO-3-METHYL-PHENOL is utilized as a key building block in the creation of a wide range of organic compounds, expanding the scope of chemical research and innovation.
Used in Antifungal and Antimicrobial Applications:
4-IODO-3-METHYL-PHENOL is employed as an active ingredient in topical antiseptics and disinfectants, leveraging its antifungal and antimicrobial properties to combat infections and promote healing.
Used in Polymer Production:
This chemical is incorporated in the manufacturing process of polymers, enhancing their properties and expanding their applications in various industries.

InChI:InChI=1/C7H7IO/c1-5-4-6(9)2-3-7(5)8/h2-4,9H,1H3

Upstream product

• 2835-99-6 4-amino-3-methylphenol 
• 108-39-4 3-methyl-phenol 

Downstream Products

• 108-39-4 3-methyl-phenol 
• 906673-24-3 AN₂₇₂₈ 
• 947162-07-4 4-(4-cyanophenoxy)-2-methylphenylboronic acid 
• 57556-31-7 4-hydroxy-2-methylbenzoic acid methyl ester 
• 845623-01-0 Boc-(2'-monomethyltyrosine)-Pro-Phe-Phe-NH₂ 
• 137378-58-6 (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2-methylphenyl)propanoic acid 
• 845622-75-5 4-acetoxy-N-acetyl-2-methyl-L-tyrosine methyl ester 
• 845622-69-7 methyl (Z)-2-acetamido-3-(4-acetoxy-2-methylphenyl)-propenoate 
• 845622-63-1 4-iodo-3-methylphenol acetate 
• 156878-04-5 Methanesulfonic acid 4-iodo-3-methyl-phenyl ester 

Relevant articles and documents

METHOD FOR PREPARING CRISABOROLE

The invention relates to a method for preparing Crisaborole of Formula I, comprising using m-methylphenol as the starting material to obtain a target product through a five-step reaction. The starting materials and the raw materials used in each step of the method according to the present invention are cheap and easy to obtain, and the process is simple. The reaction of introducing boron atoms into the benzene ring to form an oxygen boron heterocycle is novel, with high yield and mild conditions, and is suitable for industrial production.

Preparation method of crisaborole

The invention discloses a preparation method of crisaborole. The preparation method comprises the following steps: by taking m-methylphenol as a raw material, firstly coupling the m-methylphenol with 4-halogenated-cyanophenyl, and then under the action of a halogenating reagent, increasing the yield of an intermediate product 4-(4-halogen-3-methylphenoxy) cyanophenyl; and carrying out halogen-metal exchange, halogenation, ring closing and other reactions to prepare the crisaborole. Compared with the prior art, the method has advantages that the raw materials are cheap and easy to obtain, and expensive reagents and raw materials in the prior art are not used; the reaction is mild, and ultralow-temperature reaction in the prior art can be avoided; the method is short in reaction time, free of column chromatography purification, simple in process, convenient to operate and suitable for industrial production.

Ultrasonically assisted halogenation of aromatic compounds using isoquinolinium bound hypervalent chromium and tetrabutylammonium halides in PEG-600 solutions under acid free and solvent-free conditions

Isoquinolinium bound Cr(VI) reagents like isoquinolinium dichromate (IQDC) and isoquinolinium chlorochromate (IQCC) have been successfully accomplished as efficient reagents for oxidative halogenation of aromatic compounds using tetrabutylammonium halide (TBAX) as halogenating agents in aqueous polyethylene glycol (PEG-600) under acid free conditions. Tetrabutylammonium bromide (TBAB) has been used for bromination and tetrabutylammonium iodide (TBAI) for iodination. The halogenation reactions that occurred smoothly in 2 to 7 h under conventional conditions are accelerated magnificently under sonication with few minutes (25 to 70 min) of reaction time and fairly good yields. The reactions occurred at moderate temperature under mild and environmentally safe conditions with simple work up.

A green catalytic method for selective synthesis of iodophenols via aerobic oxyiodination under organic solvent-free conditions

A highly efficient catalytic method for aerobic oxyiodination of various phenols catalysed by copper(II) nitrate was achieved under mild conditions using I2as an iodinating reagent, molecular oxygen as an oxidant, and water as a solvent. The catalyst shows not only high activity for phenols with either electron-donating or electron-withdrawing groups, but also a remarkable selectivity for the formation of para-iodo substituted phenols. This study offers a green method for iodination of aromatic phenols with high atom economy.

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.

TETRASUBSTITUTED ALKENE COMPOUNDS AND THEIR USE

Disclosed herein are compounds, or pharmaceutically acceptable salts thereof, and methods of using the compounds for treating breast cancer by administration to a subject in need thereof a therapeutically effective amount of the compounds or pharmaceutically acceptable salts thereof. The breast cancer may be an ER-positive breast cancer and/or the subject in need of treatment may express a mutant ER-α protein.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

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.

Regioselective iodination of aromatic compounds with potassium iodide in the presence of benzyltriphenylphosphonium perchlorate

A simple and efficient method for the selective iodination of various aromatic compounds by using potassium iodide in the presence of benzyltriphenylphosphonium perchlorate, is reported. This method provides several advantages such as good selectivity between ortho and para positions of aromatic compounds and high yields of the products.

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.