10570-67-9

Basic information

• Product Name: 2,6-DIMETHYL-4-IODOPHENOL
• Synonyms: 4-IODO-2,6-DIMETHYLPHENOL;4-IODO-2,6-XYLENOL;2,6-DIMETHYL-4-IODOPHENOL;2,6-Dimethyl-4-iodophenol 98%;4-LODO-2,6-DIMETHYL PHENOL;2-Hydroxy-5-iodo-m-xylene, 4-Iodo-2,6-xylenol
• CAS NO: 10570-67-9
• Molecular Formula: C₈H₉IO
• Molecular Weight: 248.06
• Product Categories: Aromatic Phenols
• Mol File: 10570-67-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 99 °C
• Boiling Point: 278.95 °C at 760 mmHg
• Flash Point: 122.505 °C
• Appearance: white like or light brown crystalline powder
• Density: 1.741 g/cm³
• Vapor Pressure: 0.00244mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 10.06±0.23(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 2,6-DIMETHYL-4-IODOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYL-4-IODOPHENOL(10570-67-9)
• EPA Substance Registry System: 2,6-DIMETHYL-4-IODOPHENOL(10570-67-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-60-37
• Hazardous Substances Data: 10570-67-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 5384, 1985 DOI: 10.1021/jo00225a079

InChI:InChI=1/C8H9IO/c1-5-3-7(9)4-6(2)8(5)10/h3-4,10H,1-2H3

Upstream product

• 576-26-1 2.6-dimethylphenol 

Downstream Products

• 150254-60-7 acetic acid-(4-iodo-2,6-dimethyl-phenyl ester) 
• 55215-54-8 5-iodo-2-methoxy-1,3-dimethylbenzene 
• 107311-63-7 5-{5-[4-(3-furanyl)-2,6-dimethylphenoxy]pentyl}-3-methylisoxazole 
• 107311-59-1 5-{5-[4-(2-furanyl)-2,6-dimethylphenoxy]pentyl}-3-methylisoxazole 
• 10181-98-3 5-(2,6-dimethyl-phenoxy)-2-methoxy-1,3-dimethyl-benzene 
• 18133-81-8 2-bromo-1-(2,6-dimethyl-phenoxy)-4-methoxy-3,5-dimethyl-benzene 
• 25528-29-4 2-chloromethyl-1-(2,6-dimethyl-phenoxy)-4-methoxy-3,5-dimethyl-benzene 
• 1191279-71-6 N₂-(4'-cyanophenyl)-6-(2'',6''-dimethyl-4''-iodo)phenoxy-3-nitropyridin-2-amine 
• 4919-37-3 3,5-dimethyl-4-hydroxybenzoic acid 
• 1280211-57-5 5-iodo-1,3-dimethyl-2-phenoxybenzene 
• 140681-19-2 4-[-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)ethylidene]-2,6-dimethylcyclohexa-2,5-dien-1-one 

Relevant articles and documents

An Efficient and Selective Method for the Preparation of Iodophenols

Direct iodination of a wide range of phenols may be achieved with unprecedented selectivity in aqueous alcohol solvents by the action of a reagent preparated in situ from sodium hypochlorite and sodium iodide.Para-substituted phenols (or ortho-substituted, when the para-position is already occupied) are obtained in fair to excellent yields by simple isolation techniques.The extent of iodination is easily controlled by stoichiometry.The technique is also useful with some anilines.

Oxidative and non-oxidative metabolism of 4-iodoanisole by rat liver microsomes

1. The oxidative metabolism of 4-iodoanisole (1) by liver microsomes from β-naphthoflavone-treated rats yields 4-iodophenol (2) 2-iodo-5-methoxyphenol (3), 2-methoxy-5-iodophenol (4), 4-methoxyphenol (5), and 3-methoxyphenol (6) in relative yields of 5:2:

4,5-Dimethyl-2-Iodoxybenzenesulfonic Acid Catalyzed Site-Selective Oxidation of 2-Substituted Phenols to 1,2-Quinols

A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Natural products such as biscarvacrol and lacinilene C methyl ether could be synthesized efficiently under mild reaction conditions. Furthermore, both the reaction rate and site selectivity could be further improved by the introduction of a trialkylsilylmethyl substituent at the 2-position of phenols. The corresponding 1,2-quinols could be transformed into various useful structural motifs by [4+2] cycloaddition cascade reactions.

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.