276866-90-1

Basic information

• Product Name: 4-chloro-3-iodobenzaldehyde
• Synonyms: 4-chloro-3-iodobenzaldehyde
• CAS NO: 276866-90-1
• Molecular Formula: C₇H₄ClIO
• Molecular Weight: 266.46353
• Mol File: 276866-90-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 117 °C
• Boiling Point: 304.0±27.0 °C(Predicted)
• Appearance: /
• Density: 1.971±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-chloro-3-iodobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-3-iodobenzaldehyde(276866-90-1)
• EPA Substance Registry System: 4-chloro-3-iodobenzaldehyde(276866-90-1)

Safety Data

• Hazardous Substances Data: 276866-90-1(Hazardous Substances Data)

Usage

General Description

4-Chloro-3-iodobenzaldehyde is a chemical compound with the formula C7H4ClIO. It is a pale yellow solid that is used as an intermediate in the synthesis of various organic compounds. This chemical is mainly used in the pharmaceutical industry for the development of new drugs and active pharmaceutical ingredients. It is also employed in the field of organic chemistry for the preparation of complex molecules. Additionally, 4-chloro-3-iodobenzaldehyde has potential applications in agrochemicals and material science due to its unique reactivity and structural properties. However, it is important to handle this compound with care, as it can pose health and environmental risks if not managed properly.

Upstream product

• 16588-34-4 4-chloro-3-nitro-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 104317-95-5 (4-chloro-3-iodo-phenyl)-methanol 

Downstream Products

• 42860-04-8 4-chloro-3-iodobenzoic acid 
• 914106-25-5 4-chloro-3-iodobenzaldoxime 
• 914106-26-6 4-chloro-3-iodobenzonitrile 
• 914106-29-9 4-chloro-4-[2-(trimethylsilyl)ethynyl]benzonitrile 
• 914106-33-5 4-chloro-3-(3-hydroxy-3-methylbut-1-ynyl)benzonitrile 
• 914106-00-6 4-chloro-3-ethynylbenzonitrile 
• 204919-70-0 3-ethynyl-4-methoxybenzonitrile 
• 914106-16-4 3-(4-cyanophenyl)-5-(2-chloro-5-cyanophenyl)isoxazole 
• 914106-20-0 3-(4-cyano-2-nitrophenyl)-5-(5-cyano-2-methoxyphenyl)isoxazole 
• 914106-21-1 3-(4-cyano-2-methoxyphenyl)-5-(5-cyano-2-methoxyphenyl)isoxazole 
• 914106-22-2 3-(3-cyanophenyl)-5-(2-chloro-5-cyanophenyl)isoxazole 
• 914106-24-4 3,5-bis(5-cyano-2-methoxyphenyl)isoxazole 
• 914105-93-4 5-(5-cyano-2-methoxyphenyl)-3-(3-cyanophenyl)isoxazole 
• 915944-55-7 C₉H₈ClIO₂ 

Relevant articles and documents

Discovery of G Protein-Biased Ligands against 5-HT7R

There has been significant attention concerning the biased agonism of G protein-coupled receptors (GPCRs), and it has resulted in various pharmacological benefits. 5-HT7R belongs to a GPCR, and it is a promising pharmaceutical target for the treatment of neurodevelopmental and neuropsychiatric disorders. Based on our previous research, we synthesized a series of 6-chloro-2′-methoxy biphenyl derivatives 1, 2, and 3 with a variety of amine scaffolds. These compounds were evaluated for their binding affinities to 5-HTR subtypes and their functional selectivity toward the Gs protein and the β-arrestin signaling pathways of 5-HT7R. Among them, 2-(6-chloro-2′-methoxy-[1,1′-biphenyl]-3-yl)-N-ethylethan-1-amine, 2b, was found to be a G-protein-biased ligand of 5-HT7R. In an in vivo study with Shank3 transgenic mice, the self-grooming behavior test was performed with 2b, which increased the duration of self-grooming. The experiments further suggested that 5-HT7R is associated with autism spectrum disorders (ASDs) and could be a therapeutic target for the treatment of stereotypy in ASDs.

5-HT7receptor modulators: Amino groups attached to biphenyl scaffold determine functional activity

5-HT7receptor (5-HT7R) agonists and antagonists have been reported to be used for treatment of neuropathic pain and depression, respectively. In this study, as a novel scaffold for 5-HT7R modulators, we designed and prepared a series of biphenyl-3-yl-methanamine derivatives with various amino groups. Evaluation of functional activities as well as binding affinities of the title compounds identified partial agonists (EC50?=?0.55–3.2?μM) and full antagonists (IC50?=?5.57–23.1?μM) depending on the amino substituents. Molecular docking study suggested that the ligand-based switch in functional activity from agonist to antagonist results from the size of the amino groups and thereby different binding modes to 5-HT7R. In particular, interaction of the ligand with Arg367 of 5-HT7R is shown to differentiate agonists and antagonists. In the pharmacophore model study, two distinct pharmacophore models can tell whether a ligand is an agonist or an antagonist. Taken together, this study provides valuable information for designing novel compounds with selective agonistic or antagonistic properties against 5-HT7R.

Oxidative iodination of deactivated arenes in concentrated sulfuric acid with I2/NaIO4 and KI/NaIO4 iodinating systems

Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields. Georg Thieme Verlag Stuttgart.