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

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

Downstream Products

• 179253-65-7 ((2-(benzyloxy)phenyl)ethynyl)trimethylsilane 
• 889129-35-5 1-(2-benzyloxy-phenyl)-piperidin-2-one 
• 889129-38-8 1-(2-benzyloxy-phenyl)-azepan-2-one 
• 914604-18-5 (E)-1-(2-benzyloxy-3,6-dimethoxyphenyl)-4-(2-benzyloxyphenyl)-1-triethylsilyloxybut-3-en-2-one 
• 914604-21-0 (E)-1-(3-benzyloxy-1,4,5,6,8-pentamethoxynaphthalen-2-yl)-4-(2-benzyloxyphenyl)-1-triethysilanyloxybut-3-en-2-one 
• 170651-16-8 1-phenylmethyloxy-2-(1-propynyl)benzene 
• 67191-36-0 1-(benzyloxy)-2-ethenylbenzene 
• 1094615-24-3 1-benzyloxy-2-[(2-methoxyphenyl)ethynyl]benzene 
• 190661-29-1 2-benzyloxyphenylboronic acid 
• 2005-10-9 6H-benzo[c]chromen-6-one 
• 1360622-36-1 (2-(benzyloxy)phenyl)(4-chlorophenyl)methanone 
• 168301-25-5 3',5'-dimethoxy[1,1'-biphenyl]-2-ol 

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

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.