25245-29-8

Usage

Uses

Used in Organic Synthesis:
5-IODO-1,2,3-TRIMETHOXYBENZENE is used as a primary and secondary intermediate in organic synthesis for the development of various chemical compounds. Its iodine atom and methoxy groups provide opportunities for further chemical reactions, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
In the pharmaceutical industry, 5-IODO-1,2,3-TRIMETHOXYBENZENE can be used as a key intermediate for the synthesis of drugs with specific therapeutic properties. Its unique structure allows for the creation of novel compounds that can target various biological pathways and diseases.
In the agrochemical industry, 5-IODO-1,2,3-TRIMETHOXYBENZENE can be utilized as an intermediate in the synthesis of pesticides, herbicides, and other crop protection agents. Its chemical properties can contribute to the development of more effective and environmentally friendly products.
In the field of specialty chemicals, 5-IODO-1,2,3-TRIMETHOXYBENZENE can be employed as an intermediate for the production of dyes, pigments, and other colorants. Its structural features can lead to the creation of new compounds with unique color properties and improved performance characteristics.
Overall, 5-IODO-1,2,3-TRIMETHOXYBENZENE is a valuable intermediate in organic synthesis, with applications spanning across various industries, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure and chemical properties make it an essential component in the development of innovative and effective products.

InChI:InChI=1/C9H11IO3/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5H,1-3H3

Upstream product

• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 24313-88-0 3,4,5-Trimethoxyaniline 
• 118-41-2 Eudesmic acid 
• 1017601-55-6 potassium (3,4,5-trimethoxyphenyl)trifluoroborate 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 634-36-6 1,2,3-trimethoxybenzene 
• 6307-90-0 3,4,5-trimethoxy-1-nitrobenzene 

Downstream Products

• 53104-21-5 N-tert-Butyl-N-(3,4,5-trimethoxy-phenyl)-hydroxylamine 
• 117528-77-5 2-(3,4,5-Trimethoxy-phenyl)-2,3-dihydro-furan 
• 135755-24-7 5-{(E)-3-[3-(3,4,5-Trimethoxy-phenyl)-prop-2-ynyloxy]-propenyl}-benzo[1,3]dioxole 
• 634-36-6 1,2,3-trimethoxybenzene 
• 56772-00-0 3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl 
• 4891-62-7 4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester 
• 80141-09-9 methyl 3',4,4',5,5',6-hexamethoxybiphenyl-2-carboxylate 
• 143815-07-0 5-(cyclopent-1-en-1-yl)-1,2,3-trimethoxybenzene 
• 81952-70-7 1-(3,4,5-Trimethoxy-phenyl)-cyclohexanol 
• 81952-69-4 2-Methyl-1-(3,4,5-trimethoxy-phenyl)-propan-1-ol 
• 125106-69-6 1,3-bis(3,4,5-trimethoxyphenyl)cyclopentene 
• 125131-57-9 1,4-bis(3,4,5-trimethoxyphenyl)cyclopentene 
• 6443-69-2 3,4,5-trimethoxytoluene 
• 93653-11-3 4-methoxy-3-(3,4,5-trimethoxyphenyl)-benzoic acid 

Relevant academic research and scientific papers

Efficient Synthesis and Bioevaluation of Novel Dual Tubulin/Histone Deacetylase 3 Inhibitors as Potential Anticancer Agents

Novel dual HDAC3/tubulin inhibitors were designed and efficiently synthesized by combining the pharmacophores of SMART (tubulin inhibitor) and MS-275 (HDAC inhibitor), among which compound 15cwas found to be the most potent and balanced HDAC3/tubulin dual inhibitor with high HDAC3 activity (IC50= 30 nM) and selectivity (SI > 1000) as well as excellent antiproliferative potency against various cancer cell lines, including an HDAC-resistant gastric cancer cell line (YCC3/7) with IC50values in the range of 30-144 nM. Compound 15cinhibited B16-F10 cancer cell migration and colony formation. In addition, 15cdemonstrated significantin vivoantitumor efficacy in a B16-F10 melanoma tumor model with a better TGI (70.00%, 10 mg/kg) than that of the combination of MS-275 and SMART. Finally, 15cpresented a safe cardiotoxicity profile and did not cause nephro-/hepatotoxicity. Collectively, this work shows that compound 15crepresents a novel tubulin/HDAC3 dual-targeting agent deserving further investigation as a potential anticancer agent.

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.

One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes

A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.

Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen: Development of a base-catalyzed iododeboronation for radiolabeling applications

An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: General Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications.

A one-pot radioiodination of aryl amines: Via stable diazonium salts: Preparation of 125I-imaging agents

An operationally simple, one-pot, two-step tandem procedure that allows the incorporation of radioactive iodine into aryl amines via stable diazonium salts is described. The mild conditions are tolerant of various functional groups and substitution patterns, allowing late-stage, rapid access to a wide range of 125I-labelled aryl compounds and SPECT radiotracers.

Late stage iodination of biologically active agents using a one-pot process from aryl amines

A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(ii) dichloride reduction and the use of the one-pot diazotisation-iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-d-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.

Assembly of twisted luminescent architectures based on acenaphtho[1,2-k]fluoranthene derivatives

Acenaphtho[1,2-k]fluoranthene derivatives DPAF-n as new building blocks for one-dimensional (1D) structure assembly have been developed and employed to fabricate luminescent twisted nano/micro-wires; and the DPAF rigid core attached via flexible alkyl cha

Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.

Cu-catalyzed fluorination of diaryliodonium salts with KF

A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a CuI/CuIII catalytic cycle.

Novel syntheses of fluorenones via nitrile-directed palladium-catalyzed C-H and dual C-H bond activation

Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.