25245-37-8

Usage

General Description

1-iodo-2,3,4-trimethoxybenzene, also known as 2,3,4-trimethoxy-iodobenzene, is a chemical compound that belongs to the group of iodobenzenes. It consists of a benzene ring with three methoxy groups and one iodine atom attached to it. It is commonly used in organic synthesis as a reagent for various chemical reactions, such as halogenation and nucleophilic substitution. 1-iodo-2,3,4-trimethoxybenzene has potential applications in pharmaceuticals, agrochemicals, and material science due to its versatile reactivity and ability to be incorporated into various molecular structures. Additionally, it is important to handle and store 1-iodo-2,3,4-trimethoxybenzene with caution, as it is toxic and may cause irritation to the skin, eyes, and respiratory system if proper safety measures are not taken.

Upstream product

• 634-36-6 1,2,3-trimethoxybenzene 

Downstream Products

• 634-36-6 1,2,3-trimethoxybenzene 
• 106592-91-0 1,2,3-Trimethoxy-4-(phenylthio)benzene 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 934-00-9 3-methocycatechol 
• 21450-56-6 1,2,3,4-tetramethoxybenzene 
• 87-66-1 2-hydroxyresorcinol 
• 43020-38-8 2,3,4-trimethoxybenzonitrile 
• 71953-00-9 (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)propionic acid tert-butyl ester 
• 381222-47-5 (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2',3',4'-trimethoxyphenyl)propionic acid tert-butyl ester 
• 301823-87-0 Biphenyl-2,3,4,3',4',5'-hexaol 
• 1140509-07-4 C₂₀H₂₀O₅ 
• 1453191-41-7 3-methoxy-1-(2,3,4-trimethoxyphenyl)-7-(3,4-methylenedioxyphenyl)-4-oxa-hepta-1,6-diyne 
• 1184452-44-5 3-(2,3,4-trimethoxyphenyl)prop-2-yn-1-ol 
• 108170-85-0 2,3,4-Trimethoxy-diphenylsulfon 

Relevant academic research and scientific papers

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

Background: Hemithioindigo is a promising molecular photoswitch that has only recently been applied as a photoswitchable pharmacophore for control over bioactivity in cellulo. Uniquely, in contrast to other photoswitches that have been applied to biology,

Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generatedviaC(sp3)-H activation

Transition-metal-catalyzed cross-electrophile C(sp2)-(sp3) coupling and C-H alkylation reactions represent two efficient methods for the incorporation of an alkyl group into aromatic rings. Herein, we report a Pd-catalyzed cascade cross-electrophile coupling and C-H alkylation reaction of 2-iodo-alkoxylarenes with alkyl chlorides. Methoxy and benzyloxy groups, which are ubiquitous functional groups and common protecting groups, were utilized as crucial mediatorsviaprimary or secondary C(sp3)-H activation. The reaction provides an innovative and convenient access for the synthesis of alkylated phenol derivatives, which are widely found in bioactive compounds and organic functional materials.

Selective Claisen rearrangement and iodination for the synthesis of polyoxygenated allyl phenol derivatives

Allyl aryl ethers and allyl phenol derivatives were prepared starting from commercial or synthetized phenols. Either Williamson reaction or Et2AlCl catalyzed Claisen rearrangement was performed to obtain the polyoxygenated molecules. The pivotal allyl phenols were then modified by methylation, iodocyclization or electrophilic aromatic iodination to afford the polyoxygenated derivatives in good to excellent yields. Additionally, their antibacterial properties were also investigated against Gram-positive and Gram-negative bacteria.

A method of preparing alkoxyl monoiodo-benzene

The invention relates to a method for preparing alkoxy iodobenzene. The method comprises the following steps: adding alkoxy benzene, I2, the catalyst nitrosonium tetrafluoroborate and an organic solvent into a reaction vessel, sealing the reaction vessel, performing a magnetic stirring reaction at the temperature of 20-60 DEG C under an airy condition, cooling to the room temperature after reaction, and performing purification on the mixture after reaction through column chromatography, so as to obtain the alkoxy iodobenzene. According to the method for preparing the alkoxy iodobenzene, any other auxiliary reagent is not added expect the catalyst and the solvent, used auxiliary material is less, the utilization rate of the iodine material under the optimum condition is high, the product purity is good, the reaction can be effectively performed at the room temperature, the production cost is remarkably reduced, and as acid is not added in the reaction system, the cost of production equipment can be lowered.

Nitrogen dioxide-catalyzed electrophilic iodination of arenes

Nitrogen dioxide is demonstrated to be an effective catalyst precursor for the iodination of alkoxy-substituted benzenes and naphthalenes. Different from the transition metal catalysts, nitrogen dioxide can be easily separated from the final products, and is free of heavy metal waste. Although the present catalyst precursor is toxic, it does not stain the final products due to its low-boiling character. No other reagents apart from 0.5 equiv. of iodine (I 2), 6.5 mol% nitrogen dioxide and acetonitrile solvent were used in the iodination, and basically all the iodine atoms in the iodine source were transferred to the iodination products, showing that the presented protocol is highly atom-economic and practical. Copyright

Selective iodination of some phenols, anilines and methoxyarenes by molecular iodine in the presence of 1-butyl-3-methylimidazolium hydrogen sulphate

A simple, mild and regioselective method for the iodination of some phenols, anilines and methoxyarenes by using molecular iodine in presence of 1-butyl-3-methylimidazolium hydrogen sulphate ([bmim]-HSO4) in acetonitrile as solvent is reported. One-pot synthesis, mild reaction conditions, short reaction times and excellent yields of the products are noteworthy.

Deprotonative metalation of substituted aromatics using mixed lithium-cobalt combinations

The deprotonation of anisole was attempted using different homo- and heteroleptic TMP/Bu mixed lithium-cobalt combinations. Using iodine to intercept the metalated anisole, an optimization of the reaction conditions showed that in THF at room temperature 2 equiv of base were required to suppress the formation of the corresponding 2,2′-dimer. The origin of the dimer was not identified, but its formation was favored with allyl bromide as electrophile. The metalated anisole was efficiently trapped using iodine, anisaldehyde, and chlorodiphenylphosphine, and moderately employing benzophenone, and benzoyl chloride. 1,2-, 1,3-, and 1,4-dimethoxybenzene were similarly converted regioselectively to the corresponding iodides. It was observed that 2-methoxy- and 2,6-dimethoxypyridine were more prone to dimerization than the corresponding benzenes when treated similarly. Involving ethyl benzoate in the metalation-iodination sequence showed that the method was not suitable to functionalize substrates bearing reactive functions.

Iodination of organic compounds with elemental iodine in the presence of hydrogen peroxide in ionic liquid media

Iodo-transformations using the reagent system I2/H 2O2 were studied in the water miscible ionic liquid (IL) 1-butyl-3-methyl imidazolium tetrafluoroborate (bmimBF4) and in water immiscible IL, 1-butyl-3-methyl i

Solvent-free iodination of organic molecules using the I 2/urea-H2O2 reagent system

Introduction of iodine under solvent-free conditions into several aromatic compounds activated toward electrophilic functionalisation was found to proceed efficiently using elemental iodine in the presence of a solid oxidiser, the urea-H2O2 (UHP) adduct. Two types of iodo- functionalisation through an electrophilic process were observed: iodination of an aromatic ring, and side-chain iodo-functionalisation in the case of arylalkyl ketones. Two reaction routes were established based on the required substrate: iodine: oxidiser ratio for the most efficient iodo-transformation, and the role of UHP was elucidated in each route. The first, requiring a 1: 0.5: 0.6 stoichiometric ratio of substrate to iodine to UHP, followed the atom economy concept in regard to iodine and was valid in the case of aniline (1a), 4-t-Bu-phenol (3), 1,2-dimethoxy benzene (5a), 1,3-dimethoxy benzene (5b), 1,2,3-trimethoxy benzene (7a), 1,2,4-trimethoxy benzene (7b), 1,3,5-trimethoxy benzene (7c), 1-indanone (11a) and 1-tetralone (11b). The second reaction route, where a 1: 1: 1 stoichiometric ratio of substrate: I2: UHP was needed for efficient iodination, was suitable for side-chain iodo-functionalisations of acetophenone (1c) and methoxy-substituted acetophenones. Moreover, addition of iodine to 1-octene (13a) and some phenylacetylenic derivatives (15a, 15b) was found to proceed efficiently without the presence of any oxidiser and solvent at room temperature. This journal is The Royal Society of Chemistry.

'Green' iodination of dimethoxy- and trimethoxy-substituted aromatic compounds using an iodine-hydrogen peroxide combination in water

Mild iodination using iodine and a 30% solution of hydrogen peroxide as oxidant was performed in water. The method proved to be efficient and selective for the introduction of iodine into dimethoxybenzenes, trimethoxybenzenes, and dimethoxy- and trimethox