1948-40-9

Usage

Uses

Used in Organic Synthesis:
3,5-Diiodo-4-hydroxybenzaldehyde is used as a key intermediate in the synthesis of various organic compounds. Its unique structure, featuring two iodine atoms and a hydroxyl group attached to a benzene ring, allows it to participate in a range of chemical reactions, facilitating the creation of diverse molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-diiodo-4-hydroxybenzaldehyde is used as a building block for the development of new drugs. Its chemical properties make it suitable for the synthesis of therapeutic agents, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
3,5-Diiodo-4-hydroxybenzaldehyde is also utilized in academic and industrial research settings. It serves as a model compound for studying various chemical reactions and mechanisms, contributing to the advancement of knowledge in organic chemistry.
Used in Material Science:
In the field of material science, 3,5-diiodo-4-hydroxybenzaldehyde can be employed in the development of novel materials with specific properties. Its unique structure may be integrated into the design of new polymers, coatings, or other materials with potential applications in various industries, such as electronics, automotive, or aerospace.

InChI:InChI=1/C7H4I2O2/c8-5-1-4(3-10)2-6(9)7(5)11/h1-3,11H

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 37987-26-1 4-(hydroxymethyl)-2,6-diiodophenol 
• 780-00-7 (4-hydroxy-3,5-diiodo-phenyl)-pyruvic acid 
• 7553-56-2 iodine 
• 64-17-5 ethanol 
• 7782-68-5 iodic acid 
• 67-66-3 chloroform 
• 28177-54-0 2,6-diiodo-phenol 
• 60032-63-5 4-hydroxy-3-iodo-benzaldehyde 
• 139-02-6 sodium phenoxide 

Downstream Products

• 618-76-8 3,5-diiodo-4-hydroxybenzoic acid 
• 2296-76-6 4-hydroxy-3,5-diiodo-benzaldehyde-oxime 
• 52273-39-9 4-acetoxy-3,5-diiodo-benzaldehyde 
• 56926-77-3 4-hydroxy-3,5-diiodo-trans-cinnamic acid 
• 591210-34-3 4-benzyloxy-3,5-diiodo-benzaldehyde 
• 855264-82-3 4-cyclohex-2-enyloxy-3,5-diiodo-benzaldehyde 
• 725252-79-9 3,5-diiodo-4-methoxy-benzaldehyde dimethylacetal 
• 93087-37-7 4-(4-acetoxy-3,5-diiodo-benzylidene)-2-methyl-4H-oxazol-5-one 

Relevant academic research and scientific papers

NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl

In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.

Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate

Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.

Efficient and sustainable laccase-catalyzed iodination of: P -substituted phenols using KI as iodine source and aerial O2 as oxidant

The laccase-catalyzed iodination of p-hydroxyarylcarbonyl- and p-hydroxyarylcarboxylic acid derivatives using KI as iodine source and aerial oxygen as the oxidant delivers the corresponding iodophenols in a highly efficient and sustainable manner with yields up to 93% on a preparative scale under mild reaction conditions.

Halogenated Phenols for Diagnostics, Antioxidant Protection and Drug Delivery

The present invention provides compositions and methods for the targeted delivery, release and/or formation of a drug compound at a target site(s) within the body of an individual, such as a diseased and/or inflamed tissue in the body of the individual. These compositions may comprise a halogenated phenol ring cleavably linked to a core structure of a drug compound. Due to the variety of substituents that may be utilized in forming the different types of linkages, numerous examples of drug compounds linked to a halogenated phenol ring are proposed. The present invention further provides compositions comprising halogenated phenol starting compounds that do not undergo cleavage during a dehalogenation reaction to form a drug compound in a targeted tissue when administered to an individual. Methods of administering these non-cleaving compounds are further provided.

A Rotaxane-like Cage-in-Ring Structural Motif for a Metallosupramolecular Pd6L12 Aggregate

A BODIPY-based bis(3-pyridyl) ligand undergoes self-assembly upon coordination to tetravalent palladium(II) cations to form a Pd6L12 metallosupramolecular assembly with an unprecedented structural motif that resembles a rotaxane-like cage-in-ring arrangement. In this assembly the ligand adopts two different conformations—a C-shaped one to form a Pd2L4 cage which is located in the center of a Pd4L8 ring consisting of ligands in a W-shaped conformation. This assembly is not mechanically interlocked in the sense of catenation but it is stabilized only by attractive π-stacking between the peripheral BODIPY chromophores and the ligands’ skeleton as well as attractive van der Waals interactions between the long alkoxy chains. As a result, the co-arrangement of the two components leads to a very efficient space filling. The overall structure can be described as a rotaxane-like assembly with a metallosupramolecular cage forming the axle in a metallosupramolecular ring. This unique structural motif could be characterized via ESI mass spectrometry, NMR spectroscopy, and X-ray crystallography.

Iodination of industrially important aromatic compounds with aqueous potassium triiodide

A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.

Supramolecular Coordination Polymer Formed from Artificial Light-Harvesting Dendrimer

We report the formation of supramolecular coordination polymers formed from multiporphyrin dendrimers (PZnPM; M = FB or Cu), composed of the focal freebase porphyrin (PFB) or cupper porphyrin (PCu) with eight zinc porphyrin (PZn) wings, and multipyridyl porphyrins (PyPM; M = FB or Cu), PFB or PCu with eight pyridyl groups, through multiple axial coordination interactions of pyridyl groups to PZns. UV-vis absorption spectra were recorded upon titration of PyPFB to PZnPFB. Differential spectra, obtained by subtracting the absorption of PZnPFB without guest addition as well as the absorption of PyPFB, exhibited clear isosbestic points with saturation binding at 1 equiv addition of PyPFB to PZnPFB. Job's plot analysis also indicated 1:1 stoichiometry for the saturation binding. The apparent association constant between PZnPFB and PyPFB (2.91 × 106 M-1), estimated by isothermal titration calorimetry, was high enough for fibrous assemblies to form at micromolar concentrations. The formation of a fibrous assembly from PZnPFB and PyPFB was visualized by atomic force microscopy and transmission electron microscopy (TEM). When a 1:1 mixture solution of PZnPFB and PyPFB (20 M) in toluene was cast onto mica, fibrous assemblies with regular height (ca. 2 nm) were observed. TEM images obtained from 1:1 mixture solution of PZnPFB and PyPFB (0.1 wt %) in toluene clearly showed the formation of nanofibers with a regular diameter of ca. 6 nm. Fluorescence emission measurement of PZnPM indicated efficient intramolecular energy transfer from PZn to the focal PFB or PCu. By the formation of supramolecular coordination polymers, the intramolecular energy transfer changed to intermolecular energy transfer from PZnPM to PyPM. When the nonfluorescent PyPCu was titrated to fluorescent PZnPFB, fluorescence emission from the focal PFB was gradually decreased. By the titration of fluorescent PyPFB to nonfluorescent PZnPCu, fluorescence emission from PFB in PyPFB was gradually increased due to the efficient energy transfer from PZn wings in PZnPCu to PyPFB.

HALOGENATED PHENOLS FOR DIAGNOSTICS, ANTIOXIDANT PROTECTION AND DRUG DELIVERY

The present invention provides compositions and methods for the administration and targeted delivery, release and/or formation of a drug compound from a halogenated phenol starting compound of the present invention at site(s) within the body of an individual having high FROS, such as within a diseased and/or inflamed tissue. The present invention further provides compositions and methods for the administration of FROS scavenging compounds to an individual to protect cells and tissues from damage that might be caused by FROS. The present invention further provides compositions and methods for the detection of a detectable product, such as an indigo-like compound or other product of a dehalogenation reaction, formed from a compound of the present invention as a measurement or indication of the amount and/or localization of high FROS levels in the body of an individual.

SUBSTITUTED ISOQUINOLINES AND THEIR USE AS TUBULIN POLYMERIZATION INHIBITORS

The present invention relates generally to substituted isoquinolines and their use as tubulin polymerization inhibitors. In particular, the invention relates to substituted isoquinolines which possess useful therapeutic activity, use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds