142523-69-1

Basic information

• Product Name: 1-(benzyloxy)-2-iodobenzene
• Synonyms: 1-(benzyloxy)-2-iodobenzene
• CAS NO: 142523-69-1
• Molecular Formula: C₁₃H₁₁IO
• Molecular Weight: 310.13031
• Mol File: 142523-69-1.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(benzyloxy)-2-iodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzyloxy)-2-iodobenzene(142523-69-1)
• EPA Substance Registry System: 1-(benzyloxy)-2-iodobenzene(142523-69-1)

Safety Data

• Hazardous Substances Data: 142523-69-1(Hazardous Substances Data)

Usage

Description

1-(Benzyloxy)-2-iodobenzene is a chemical compound with the molecular formula C13H11IO. It is a benzene derivative featuring a benzyl ether group and an iodine atom attached to the benzene ring. 1-(benzyloxy)-2-iodobenzene is recognized for its unique structure and reactivity, making it a valuable intermediate in the synthesis of a variety of organic compounds.

Uses

Used in Pharmaceutical Industry:
1-(Benzyloxy)-2-iodobenzene serves as a crucial building block in organic synthesis, particularly for the production of pharmaceuticals. Its ability to participate in metal-catalyzed cross-coupling reactions allows for the formation of more complex molecules that can be utilized in developing new drugs.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 1-(Benzyloxy)-2-iodobenzene is employed as a key intermediate. Its chemical properties make it suitable for the synthesis of various agrochemicals, contributing to the development of pesticides and other agricultural products.
Used in Material Science:
1-(Benzyloxy)-2-iodobenzene also has potential applications in material science, specifically in the development of materials with controlled properties. Its unique structure lends itself to the creation of liquid crystals and organic semiconductors, which are important in the advancement of display technologies and electronic devices.
Overall, 1-(Benzyloxy)-2-iodobenzene is a versatile chemical intermediate with applications spanning across pharmaceuticals, agrochemicals, and material science, highlighting its importance in the synthesis of complex organic molecules and the development of innovative materials.

Upstream product

• 4560-41-2 2-benzyloxynitrobenzene 
• 100-51-6 benzyl alcohol 
• 1493-27-2 ortho-nitrofluorobenzene 
• 20012-63-9 o-(benzyloxy)aniline 
• 108-95-2 phenol 
• 100-39-0 benzyl bromide 
• 946-80-5 (benzyloxy)benzene 
• 533-58-4 2-Iodophenol 
• 100-44-7 benzyl chloride 

Downstream Products

• 179253-65-7 ((2-(benzyloxy)phenyl)ethynyl)trimethylsilane 
• 889129-38-8 1-(2-benzyloxy-phenyl)-azepan-2-one 
• 1195869-65-8 1-{5-[2-(2-benzyloxyphenyl)-2-oxoethyl]furan-2-yl}propan-2-one 
• 190661-29-1 2-benzyloxyphenylboronic acid 
• 1528732-89-9 7-(2-(benzyloxy)phenyl)cyclohepta-1,3,5-triene 
• 74511-44-7 o-(benzyloxy)benzonitrile 
• 1388625-59-9 C₂₂H₂₆N₂O₄ 

Relevant articles and documents

First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones

A series of novel (E)-2-(2-propargyloxystyryl)chromones and (E,E)-2-[4-(2-propargyloxyphenyl)buta-1,3-dien-1-yl]chromones were designed and synthesized via aldol condensation of 2-methylchromones with 2-propargyloxy(benzaldehyde and cinnamaldehyde), respectively. Both chromone derivatives were used as substrates in microwave-assisted intramolecular Diels-Alder reactions, affording chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones. This is the first report involving chromone derivatives in intramolecular Diels-Alder reactions for the synthesis of new oxygen heterocycles, namely xanthone- and flavone-type compounds.

Visible light mediated synthesis of 6H-benzo[c]chromenes: transition-metal-free intramolecular direct C-H arylation

A synthetic approach towards the 6H-benzo[c]chromene ring under visible light and transition-metal-free conditions has been developed. Benzochromenes are synthesized from the corresponding (2-halobenzyl) phenyl ethers or (2-halophenyl) benzyl ethers using

Structure-Based Optimization of 3-Phenyl-N-(2-(3-phenylureido)ethyl)thiophene-2-sulfonamide Derivatives as Selective Mcl-1 Inhibitors

Selective Mcl-1 inhibitors may overcome the drug resistance caused by current anti-apoptotic Bcl-2 protein inhibitors in tumors with Mcl-1 overexpression. Based on previously discovered compounds with a 3-phenylthiophene-2-sulfonamide core moiety, in this work, we have obtained new compounds with improved binding affinity and/or selectivity under the guidance of structure-based design. The most potent compounds achieved sub-micromolar binding affinities to Mcl-1 (Ki～ 0.4 μM) and good cytotoxicity (IC5015N-heteronuclear single-quantum coherence NMR spectra suggested that these compounds bound to the BH3-binding groove on Mcl-1. Several cellular assays revealed that FWJ-D4 as well as its precursor FWJ-D5 effectively induced caspase-dependent apoptosis, and their target engagement at Mcl-1 was confirmed by co-immunoprecipitation experiments. Treatment with FWJ-D5 at 50 mg/kg every 2 days on an RS4;11 xenograft mouse model for 22 days led to 75% reduction in tumor volume without body weight loss.

Synthesis of diarylalkanes through an intramolecular/intermolecular addition sequence by auto-tandem catalysis with strong Br?nsted base

An auto-tandem catalysis with a strong Br?nsted base enabled the synthesis of diarylalkanes containing a benzofuran moiety. Potassiumtert-butoxide efficiently catalyzed both the intramolecular cyclization of less acidicortho-alkynylaryl benzyl ethers and the following intermolecular addition of diarylmethanes to styrenes, demonstrating the high potential of the catalysis in organic synthesis.