90064-47-4

Usage

Uses

Used in Organic Synthesis:
4-IODO-2,5-DIMETHOXYBENZALDEHYDE is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of a wide range of organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-IODO-2,5-DIMETHOXYBENZALDEHYDE is utilized as an intermediate. Its chemical properties make it a valuable component in the synthesis of various medicinal compounds, aiding in the development of new drugs.
Used in Agrochemical Production:
Similarly, in agrochemical manufacturing, 4-IODO-2,5-DIMETHOXYBENZALDEHYDE serves as an intermediate. It is instrumental in the creation of substances used in agriculture to protect crops and enhance yields.
Used in the Preparation of 2C-I:
4-IODO-2,5-DIMETHOXYBENZALDEHYDE is used as a precursor in the illicit preparation of 2C-I, a synthetic psychedelic drug. Its role in this context is significant due to the compound's chemical reactivity and structural properties that facilitate the synthesis of the drug.
Safety Considerations:
Given its classification as a hazardous substance, 4-IODO-2,5-DIMETHOXYBENZALDEHYDE requires careful handling to prevent skin and eye irritation, ensuring the safety of those who work with it in research and industrial settings.

Upstream product

• 93-02-7 2,5-dimethoxybenzaldehyde 
• 51560-21-5 1,4-diiodo-2,5-dimethoxybenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 150-78-7 1,4-dimethoxybezene 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 90064-44-1 1-(4-iodo-2,5-dimethoxyphenyl)-2-nitropropene 
• 219726-69-9 4-iodo-2,5-dimethoxy-benzaldehyde oxime 
• 879898-80-3 2,5-dihydroxy-4-(3-methylbutyl)benzaldehyde 
• 879898-74-5 2,5-dihydroxy-4-(3-methylbut-3-en-1-ynyl)benzaldehyde 
• 879898-75-6 1,2,5-trihydroxy-4-(3-methylbut-3-en-1-ynyl)benzene 
• 879898-77-8 2,5-bis(tert-butyldimethylsilyloxy)-4-iodobenzaldehyde 
• 879898-78-9 2,5-bis(tert-butyldimethylsilyloxy)-4-(3-methylbut-3-en-1-ynyl)benzaldehyde 
• 90064-49-6 1-(4-iodo-2,5-dimethoxyphenyl)-2-propanone 
• 1360743-99-2 4-(4-(bis(4-(hexyloxy)phenyl)amino)styryl)-2,5-dimethoxybenzaldehyde 
• 1360744-02-0 4-((bis(4-(hexyloxy)phenyl)amino)styryl)-2,5-(dimethoxyphenyl)-2-cyanoacrylic acid 

Relevant academic research and scientific papers

Acid-Induced Shift of Intramolecular Hydrogen Bonding Responsible for Excited-State Intramolecular Proton Transfer

The significant progress recently achieved in designing smart acid-responsive materials based on intramolecular charge transfer inspired us to utilize excited-state intramolecular proton transfer (ESIPT) for developing a turn-on acid-responsive fluorescent system with an exceedingly large Stokes shift. Two ESIPT-active fluorophores, 2-(2-hydroxyphenyl)pyridine (HPP) and 2-(2-hydroxyphenyl)benzothiazole (HBT), were fused into a novel dye (HBT-HPP) fluorescent only in the protonated state. Moreover, we also synthesized three structurally relevant control compounds to compare their steady-state fluorescence spectra and optimized geometric structures in neutral and acidic media. The results suggest that the fluorescence turn-on was caused by the acid-induced shift of the ESIPT-responsible intramolecular hydrogen bond from the HPP to HBT moiety. This work presents a systematic comparison of the emission efficiencies and basicity of HBT and HPP for the first time, thereby utilizing their differences to construct an acid-responsive smart organic fluorescent material. As a practical application, red fluorescent letters can be written using the acid as an ink on polymer film.

Effect of Conjugation Mode on Intramolecular Charge Transfer in Fabricating Acid-Responsive Fluorophores

Solid-state acid-responsive materials are promising for the tunability of their intrinsic properties. However, the relationship between molecular structure and emission shift as a response to acid stimuli has not been systematically studied. Herein, we report the effect of protonation and subsequent intramolecular hydrogen bonding on the photophysical properties of compounds (MPP-s, MPP-d, and MPP-d-CN) with different conjugation modes between the electron-donating dimethoxyl phenyl and the electron-withdrawing benzothiazole ring. The results established that the stronger the intramolecular charge transfer feature of the compound, the smaller is the emission shift after acid stimuli. Our studies also indicated that the conjugation mode significantly affected the solid-state packing mode: MPP-s and MPP-d tended to form dimers, while MPP-d-CN exhibited the strongest aggregation-induced emission enhancement (AIEE). The exploration of structure-property relationship would provide experimental and theoretical guidance in designing acid-responsive molecular switches and developing high-performance AIEE-active luminogens.

Palladium mediated intramolecular multiple C-X/C-H cross coupling and C-H activation: Synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

Straightforward palladium mediated syntheses of calothrixin B and murrayaquinone A are described. Regioselective palladium mediated intramolecular multiple C-X/C-H cross coupling reaction on N-(4-((2-bromophenyl)amino)-2,5- dimethoxybenzyl)-N-(2-iodophenyl)acetamide followed by CAN oxidation afforded calothrixin B in excellent yield in two steps. A linear synthesis has also been developed for calothrixin B. Utilizing C-H functionalization as well as palladium mediated intramolecular C-X/C-H cross coupling reaction, murrayaquinone A synthesis was achieved. Overall, these synthetic methodologies provide an expedient entry to these biologically active alkaloids in a short reaction sequence. This journal is the Partner Organisations 2014.

Detection of amines with extended distyrylbenzenes by strip assays

We herein describe the synthesis and property evaluation of three novel aldehyde-substituted pentameric phenylenevinylenes carrying branched oligo(ethylene glycol) (swallowtail, Sw) substituents. The targets were synthesized by a combination of Heck coupling and Wittig or Horner reactions of suitable precursor modules. If the pentameric phenylenevinylene carries only two of these Sw substituents, it is no longer water-soluble. When six of the Sw substituents are attached, regardless of their position, the pentameric phenylenevinylenes are well water-soluble. The dialdehydes were investigated with respect to their amine-sensing capabilities both in water as well as in the solid state, sprayed onto thin layer chromatography (TLC) plates (alox, silica gel, reversed phase silica gel). The recognition of amine vapors using the sprayed-on phenylenevinylene dialdehydes is superb and allows the identification of different amines on regular silica TLC plates via color changes, analyzed by a statistical tool, the multivariate analysis of variance (MANOVA) protocol.

Alkyloxy substituted organic dyes for high voltage dye-sensitized solar cell: Effect of alkyloxy chain length on open-circuit voltage

Three novel organic dyes (SB1, SB2, and SB3) containing 4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline as electron donor and cyanoacrylic acid as electron acceptor bridged by alkyloxy (methyl = SB1, propyl = SB2 and hexyl = SB3) substituted p-phenylenevinylene linkers have been synthesized. Density functional theory (DFT) has employed to study electron distribution and intramolecular charge transfer. Increase in alkyl chain length in alkyloxy substituent leads to increase in open-circuit voltage (V OC), which is found to be related to the increased electron lifetime at open-circuit condition. Under AM 1.5 G 1 sun light illumination (100 mW/cm2), an optimized SB3-sensitized cell show a short-circuit photocurrent density (JSC) of 12.83 mA/cm2, an open-circuit voltage (VOC) of 0.745 V and a fill factor (FF) of 0.64, corresponding to an overall conversion efficiency (η) of 6.12%. Little degradation in η observed over 40 days is indicative of long-term stability of the SB-series dyes.

Multiple bond-conjugated photoinduced nitric oxide releaser working with two-photon excitation

Four novel nitric oxide (NO) releasers working via two-photon excitation (TPE), based on an acceptor-donor-acceptor (A-D-A) molecular design, were synthesized. Their decomposition and NO release in response to one-photon excitation, and their decomposition in response to two-photon excitation were examined. Their photoinduced decomposition characteristics are discussed.

High performance organic photosensitizers for dye-sensitized solar cells

We report highly efficient organic photosensitizers containing π-conjugated alkoxy-substituted oligophenylenevinylene linkers with electron donor-acceptor units for dye-sensitized solar cells. TA-DM-CA showed an overall solar-to-energy conversion efficiency of 9.67% at AM 1.5 illumination (100 mW cm-2).

Comparison of iodination of methoxylated benzaldehydes and related compounds using iodine/silver nitrate and iodine/periodic acid

Iodination of the three methoxybenzaldehydes, four dimethoxybenzaldehydes, vanillin, and piperonal by two methods were compared. Iodine and periodic acid gave better yields for iodination for the methoxybenzaldehydes, whereas iodine and silver nitrate generally gave better yields for the rest of the compounds. Copyright Taylor & Francis Group, LLC.

Chromogenic meroterpenoids from the mushrooms Russula ochroleuca and R. viscida

The spirodioxolactone ochroleucin A1 (1) is responsible for the red colour produced when the stalk base of Russula ochroleuca and R. viscida is treated with aqueous KOH. The labile chromogen rearranges easily into the isomeric dilactone ochrole

Selective preparation of 4-(bromo or iodo)-2,5-dimethoxybenzonitrile and 2-(bromo or iodo)-3,6-dimethoxybenzonitrile from 2,5-dimethoxybenzaldehyde

By use of appropriate reactions and sequence of steps, 2,5- dimethoxybenzaldehyde can be converted either to 4-(bromo or iodo)-2,5- dimethoxybenzonitrile or 2-(bromo or iodo)-3,6-dimethoxybenzonitrile.