35928-80-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Iodo-5-methyl-phenol is utilized as an intermediate in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its chemical properties.
Used as a Disinfectant and Fungicide:
2-Iodo-5-methyl-phenol serves as a disinfectant and fungicide, leveraging its antimicrobial properties to control the growth of microorganisms and fungi, which is crucial in various sanitation and preservation applications.
Used in the Production of Dyes and Perfumes:
2-Iodo-5-methyl-phenol is also employed in the manufacturing process of dyes and perfumes, where its chemical structure plays a role in the color and scent characteristics of the final products.

Upstream product

• 2835-98-5 2-Hydroxy-4-methylanilin 
• 108-39-4 3-methyl-phenol 
• 1260425-70-4 C₅H₄NSi(CH(CH₃)2)2C₆H₃I(CH₃) 
• 1232692-96-4 C₁₈H₂₅NSi 
• 591-17-3 meta-bromotoluene 
• 5326-39-6 4-iodo-3-nitrotoluene 
• 57234-27-2 1-(methoxymethoxy)-3-methylbenzene 
• 13194-69-9 2-iodo-5-methylaniline 

Downstream Products

• 50400-64-1 7-methylflavone 
• 130900-95-7 (Z)-2-benzylidene-6-methylbenzofuran-3(2H)-one 
• 210559-94-7 (S)-1,2-Dimethyl-cyclopent-2-enecarboxylic acid 2-iodo-5-methyl-phenyl ester 
• 630110-53-1 6,6-dimethyl-5,6-dihydro-4H-pyran-2-carboxylic acid 2-iodo-5-methyl-phenyl ester 
• 33008-48-9 6-Methyl-2-phenylbenzofuran 
• 10539-88-5 debromo-laurinterol 
• 210559-96-9 2-((1R,2S)-2-Hydroxymethyl-1,2-dimethyl-cyclopentyl)-5-methyl-phenol 
• 210559-99-2 (1S,2R,5R)-2-(2-Benzyloxy-4-methyl-phenyl)-1,2-dimethyl-bicyclo[3.1.0]hexane 
• 210559-97-0 (1S,2S)-2-(2-Benzyloxy-4-methyl-phenyl)-1,2-dimethyl-cyclopentanecarbaldehyde 
• 210559-98-1 C₂₉H₃₄N₂O₃S 
• 173992-11-5 1-(3-hydroxy-3-methylbutynyl)-4-methyl-2-tosyloxybenzene 
• 1258932-72-7 2-(2-iodo-5-methylphenoxy)-1-phenylethan-1-one 
• 1354728-90-7 2-ethynyl-5-methylphenyl acetate 
• 1354728-60-1 dimethyl 2-(2-acetoxy-4-methylphenyl)cycloprop-2-ene-1,1-dicarboxylate 

Relevant academic research and scientific papers

Study on the synthesis of the cyclopenta[f]indole core of raputindole A

The raputindoles from the rutaceous tree Raputia simulans share a cyclopenta[f]indole partial structure the synthesis of which is subject of this investigation. An efficient route to a series of 1,5-di(indol-6-yl)pentenones was developed via Mo/Au-catalyz

Palladium-Catalyzed Chemoselective Oxidative Addition of Allyloxy-Tethered Aryl Iodides: Synthesis of Medium-Sized Rings and Mechanistic Studies

This Letter describes a Pd-catalyzed Tsuji-Trost-type/Heck reaction with allyloxy-tethered aryl iodides and aziridines. The strategy provides efficient access to benzannulated medium-sized rings via intermolecular cyclization. The substrate aryl iodide ha

CRYSTALLINE ANTI-TRICHOPHYTON AGENTS AND PREPARATION PROCESS THEREOF

A crystal form of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-5-methylphenol which is stable and has high purity for preservation, industrial manufacturing, and circulation, and process for providing the same by using a boron compound.

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.

Stable axial chirality in metal complexes bearing 4,4′-substituted BIPHEPs: Application to catalytic asymmetric carbon-carbon bond-forming reactions

Not only electronic but also steric effects of 4,4′-substituents in BIPHEP derivatives and metal (Pd, Pt, and Au) complexes are shown to influence the stability of the biphenyl single bond rotation. While electron-donating or sterically demanding substituents on the 4,4′-positions destabilize the axial chirality of BIPHEP derivatives, electron-withdrawing or sterically less demanding ones on the 4,4′-positions stabilize the axis chirality. Particularly, the axial chirality of palladium dichloride complexes bearing BIPHEP with t-Bu and CF3 substituents on the 4,4′-positions is most labile and stable, respectively (ΔG≠ = 29.22 and 30.49 kcal mol-1 at 300 K; t1/2 = 7 and 56 years at 300 K). These enantiopure dicationic BIPHEPPd complexes can be employed for catalytic enantioselective arylation, alkenylation, and ene reactions to give the corresponding products in good-to-excellent yields and enantioselectivities. Significantly, in the carbonyl-ene reaction of trifluoropyruvate with isobutene, the turnover frequency (TOF) reached 58200 h-1. The remarkable effects of 4,4′-substituents in BIPHEP derivatives can be employed as a guiding principle in the design of versatile and efficient ligands.

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.

The pyridyldiisopropylsilyl group: A masked functionality and directing group for monoselective ortho-Acyloxylation and ortho-Halogenation reactions of arenes

A novel, easily removable and modifiable silicon-tethered pyridyldiisopropylsilyl directing group for C-H functionalizations of arenes has been developed. The installation of the pyridyldiisopropylsilyl group can efficiently be achieved via two complementary routes using easily available 2-(diisopropylsilyl)pyridine (5). The first strategy features a nucleophilic hydride substitution at the silicon atom in 5 with aryllithium reagents generated in situ from the corresponding aryl bromides or iodides. The second milder route exploits a highly efficient room-temperature rhodium(I)-catalyzed cross-coupling reaction between 5 and aryl iodides. The latter approach can be applied to the preparation of a wide range of pyridyldiisopropylsilyl- substituted arenes possessing a variety of functional groups, including those incompatible with organometallic reagents. The pyridyldiisopropylsilyl directing group allows for a highly efficient, regioselective palladium(II)-catalyzed mono-ortho-acyloxylation and ortho-halogenation of various aromatic compounds. Most importantly, the silicon-tethered directing group in both acyloxylated and halogenated products can easily be removed or efficiently converted into an array of other valuable functionalities. These transformations include protio-, deuterio-, halo-, boro-, and alkynyldesilylations, as well as a conversion of the directing group into the hydroxy functionality. In addition, the construction of aryl-aryl bonds via the Hiyama-Denmark cross-coupling reaction is feasible for the acetoxylated products. Moreover, the ortho-halogenated pyridyldiisopropylsilylarenes, bearing both nucleophilic pyridyldiisopropylsilyl and electrophilic aryl halide moieties, represent synthetically attractive 1,2-ambiphiles. A unique reactivity of these ambiphiles has been demonstrated in efficient syntheses of arylenediyne and benzosilole derivatives, as well as in a facile generation of benzyne. In addition, preliminary mechanistic studies of the acyloxylation and halogenation reactions have been performed. A trinuclear palladacycle intermediate has been isolated from a stoichiometric reaction between diisopropyl(phenyl)pyrid-2-ylsilane (3a) and palladium acetate. Furthermore, both C-H functionalization reactions exhibited equally high values of the intramolecular primary kinetic isotope effect (kH/k D=6.7). Based on these observations, a general mechanism involving the formation of a palladacycle via a C-H activation process as the rate-determining step has been proposed.

A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.

Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate

An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycou-marins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H 2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electronrich C3, are some of the key advantageous features of the method. Georg Thieme Verlag Stuttgart.

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.