80826-86-4

Basic information

• Product Name: 3,5-DIMETHYL-4-IODOPHENOL
• Synonyms: 3,5-DIMETHYL-4-IODOPHENOL;4-IODO-3,5-XYLENOL;4-IODO-3,5-DIMETHYL-PHENOL;5-Hydroxy-2-iodo-m-xylene;5-Hydroxy-2-iodo-m-xylene, 4-Iodo-3,5-xylenol;Phenol, 4-iodo-3,5-dimethyl-;3,5-Xylenol, 4-iodo-
• CAS NO: 80826-86-4
• Molecular Formula: C₈H₉IO
• Molecular Weight: 248.06
• Product Categories: CHIRAL CHEMICALS
• Mol File: 80826-86-4.mol

Chemical Properties

• Melting Point: 129 °C
• Boiling Point: 293 °C at 760 mmHg
• Flash Point: 131 °C
• Appearance: /
• Density: 1.74 g/cm³
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.59±0.23(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 3,5-DIMETHYL-4-IODOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYL-4-IODOPHENOL(80826-86-4)
• EPA Substance Registry System: 3,5-DIMETHYL-4-IODOPHENOL(80826-86-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 80826-86-4(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow crystalline

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

Upstream product

• 108-68-9 3,5-Dimethylphenol 

Downstream Products

• 90609-47-5 1-iodo-2,6-dimethyl-4-methoxybenzene 
• 80826-91-1 9-hydroxy-9-(2,6-dimethyl-4-hydroxyphenyl)fluorene 
• 80826-84-2 4-methylene-2,6-dimethyl-2,5-cyclohexadien-1-one 
• 80826-85-3 4-methylene-2,6-ditert-butyl-2,5-cyclohexadien-1-one 
• 145235-84-3 4-iodo-3,5-dimethylphenyl acetate 
• 80826-83-1 4-methylene-2,5-cyclohexadien-1-one 
• 378185-88-7 tert-butyl(4-iodo-3,5-dimethylphenoxy)dimethylsilane 
• 550373-08-5 1-iodo-4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2,6-dimethlbenzene 
• 872258-58-7 2,6-dimethyl-4'-(trifluoromethyl)biphenyl-4-ol 
• 779354-81-3 5-decyloxy-2-iodo-1,3-dimethylbenzene 
• 550373-10-9 1-ethynyl-4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2,6-dimethlbenzene 
• 550373-09-6 1-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-3,5-dimethl-4-(triethylsilylethynyl)benzene 
• 550373-11-0 1,6-bis(4-{2-[2-(methoxyethoxy)ethoxy]ethoxy}-2,6-dimethylphenyl)hexa-1,5-diyne-3,4-dione 
• 550373-12-1 6,7-dicyano-2,3-bis(4-{2-[2-(methoxyethoxy)ethoxy]ethoxy}-2,6-dimethylphenylethynyl)quinoxaline 

Relevant articles and documents

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.

New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling

Peptidyl-acyloxymethyl ketones (AOMKs) belong to a class of selective, irreversible inhibitors (activity-based probes) widely used as chemical tools of investigating proteins, for example, in activity-based protein profiling. The synthesis of the AOMKs has always been challenging and current methodologies involve both solution and solid-phase synthesis. Herein, the synthesis of a new scaffold useful for the preparation of peptidyl-AOMKs is reported and it is demonstrated that the new synthetic probes bearing a 4-functionalized 2,6-dimethylbenzoate efficiently inhibit cysteine proteases like cathepsin B.

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.

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.

Selectivity enhancement of aromatic halogenation reactions at the micellar interface: Effect of highly ionic media

Halogenation (iodination and bromination) of various aromatic compounds has been studied in micellar media in order to observe the effect on regioselectivity and conversion of the reaction. The addition of surfactant causes a change in the chemical shifts of the aromatic proton resonance of phenol which proves the orientation of the aromatic compound on the micellar surface. However, increase in ionic strength of the reaction media affects the selectivity of reaction by disturbing this spatial orientation of the aromatic compound in the micelle. Selectivity towards particular isomers is dependent on the concentration of the surfactant. In bromination of chlorobenzene (deactivated aromatic compound) enhancement in selectivity and conversion towards the para isomer has been observed.

Development of an asymmetric hydrogenation route to (S)- N -Boc-2,6-dimethyltyrosine

An improved, simpler and potentially more economical route to (S)-N-Boc-2,6-dimethyltyrosine 1, based on a previously published route, is presented. Key modifications were to prepare the dehydroaminoacid hydrogenation substrate 6 in a one-pot process directly from serine methyl ester and 4-iodo-3,5-dimethylphenyl acetate 4 and to identify a significantly more active asymmetric hydrogenation catalyst that allowed a 5-fold reduction in catalyst loading.

Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide

An efficient synthesis of 1-iodoalkynes and iodophenols was easily achieved by employing simple KI and TBHP. The reaction does not involve the use of a metal and base combination. A variety of substituted alkynes and phenols were prepared with good to excellent yield.

Iodination of aromatic compounds using potassium iodide and hydrogen peroxide

A simple, efficient, regioselective, and ecofriendly method for oxyiodination of aromatic compounds is presented. In this method, the electrophilic substitutions of iodine generated in situ from KI as an iodine source and hydrogen peroxide as an oxygen source have been employed without any catalyst/mineral acid for the first time. Copyright Taylor & Francis Group, LLC.

Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents

o-Methyl-substituted Me-IBX is the first modified analog of IBX that oxidizes alcohols in common organic solvents at room temperature, due to a composite of two factors, that is, low solubility and hypervalent twisting-promoted rate enhancement. Furthermore, the reagent is efficient for selective oxidation of sulfides to sulfoxides, a transformation that otherwise occurs only sluggishly with standard IBX. The facile synthetic accessibility and its mild as well as non-hazardous nature render Me-IBX a stable equivalent of Dess-Martin periodinane reagent in organic oxidations.

Eco-friendly oxyiodination of aromatic compounds using ammonium iodide and hydrogen peroxide

A new eco-friendly procedure for the oxyiodination of aromatic compounds with NH4I as an iodine source and H2O2 as an oxidant without any catalyst is presented.