90064-47-4

Basic information

• Product Name: 4-IODO-2,5-DIMETHOXYBENZALDEHYDE
• Synonyms: 4-IODO-2,5-DIMETHOXYBENZALDEHYDE
• CAS NO: 90064-47-4
• Molecular Formula: C₉H₉IO₃
• Molecular Weight: 292.07
• Mol File: 90064-47-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 109 °C
• Boiling Point: 376.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.706±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-IODO-2,5-DIMETHOXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODO-2,5-DIMETHOXYBENZALDEHYDE(90064-47-4)
• EPA Substance Registry System: 4-IODO-2,5-DIMETHOXYBENZALDEHYDE(90064-47-4)

Safety Data

• Hazardous Substances Data: 90064-47-4(Hazardous Substances Data)

Usage

General Description

4-IODO-2,5-DIMETHOXYBENZALDEHYDE is a chemical compound with the molecular formula C9H9IO3. It is a white to off-white crystalline powder that is insoluble in water but soluble in organic solvents. 4-IODO-2,5-DIMETHOXYBENZALDEHYDE is commonly used in organic synthesis and as an intermediate in the production of pharmaceuticals and agrochemicals. It is also used in the preparation of 2C-I, a synthetic psychedelic drug. 4-IODO-2,5-DIMETHOXYBENZALDEHYDE is classified as a hazardous substance and should be handled with care due to its potential to cause skin and eye irritation.

Upstream product

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

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 
• 1208264-48-5 2,5-dimethoxy-4-[2-(3,5-dimethyl-4-nitrophenyl)ethenyl]iodobenzene 
• 1208264-49-6 2,5-dimethoxy-4-(2-trimethylsilylethynyl)benzenecarbaldehyde 
• 1208264-53-2 2,5-dimethoxy-4-(2-trimethylsilylethenyl)benzenecarbaldehyde 
• 1221269-81-3 C₃₁H₂₉NO₅ 
• 1221269-86-8 C₄₁H₃₉NO₇ 
• 1221269-76-6 C₄₄H₄₀N₂O₈ 

Relevant articles and documents

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.

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.

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.