1226896-38-3

Basic information

• Product Name: (R,R)-2-Iodo-1,3-bis[1-(MesitylcarbaMoyl)ethoxy]benzene
• Synonyms: (R,R)-2-Iodo-1,3-bis[1-(MesitylcarbaMoyl)ethoxy]benzene;(R,R)-2-Iodo-1,3-bis[1-(2,4,6-trimethylphenylcarbamoyl)ethoxy]benzene;(2R,2'R)-2,2'-[(2-Iodo-1,3-phenylene)bis(oxy)]bis[N-(2,4,6-trimethylphenyl)propanamide];(2R,2'R)-2,2'-((2-Iodo-1,3-phenylene)bis(oxy))bis(N-mesitylpropanamide)
• CAS NO: 1226896-38-3
• Molecular Formula: C₃₀H₃₅IN₂O₄
• Molecular Weight: 614.51437
• Mol File: 1226896-38-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: 0-10°C
• CAS DataBase Reference: (R,R)-2-Iodo-1,3-bis[1-(MesitylcarbaMoyl)ethoxy]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-2-Iodo-1,3-bis[1-(MesitylcarbaMoyl)ethoxy]benzene(1226896-38-3)
• EPA Substance Registry System: (R,R)-2-Iodo-1,3-bis[1-(MesitylcarbaMoyl)ethoxy]benzene(1226896-38-3)

Safety Data

• Hazardous Substances Data: 1226896-38-3(Hazardous Substances Data)

Usage

Description

(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is an asymmetrical organic compound characterized by the presence of two iodo groups and a benzene ring, to which two (R,R)-1-(Mesitylcarbamoyl)ethoxy groups are attached. This unique structure endows the molecule with distinctive chiral properties, making it a valuable asset in the realm of organic synthesis and catalysis.

Uses

Used in Organic Synthesis:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is utilized as a chiral building block for the synthesis of various organic compounds. Its specific stereochemistry contributes to the creation of enantiomerically pure products, which is crucial for the development of pharmaceuticals and agrochemicals with desired biological activities.
Used in Catalyst and Ligand Design:
In the field of catalysis, (R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene serves as a precursor for the design and synthesis of chiral catalysts and ligands. Its reactivity and structural features enable the development of catalysts that can selectively promote specific reactions, enhancing the efficiency and selectivity of chemical processes.
Used in Research and Development:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is also employed in academic and industrial research settings. Its unique properties make it an important tool for investigating the mechanisms of asymmetric reactions and for the discovery of new chiral compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is used as a key intermediate in the synthesis of chiral drugs. Its ability to produce enantiomerically pure compounds is essential for the development of drugs with improved efficacy and reduced side effects, as the biological activity of enantiomers can differ significantly.
Used in Agrochemical Industry:
In the agrochemical sector, (R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is utilized as a starting material for the synthesis of chiral pesticides and herbicides. The production of enantiomerically pure compounds ensures that only the desired enantiomer with the required biological activity is used, reducing the environmental impact and improving the safety of these chemicals.
Used in Materials Science:
(R,R)-2-Iodo-1,3-bis[1-(Mesitylcarbamoyl)ethoxy]benzene is also applied in the development of chiral materials with specific properties, such as optical activity or selectivity in molecular recognition. These materials have potential applications in various fields, including sensors, catalysts, and advanced materials for electronics and photonics.

Upstream product

• 1226896-33-8 (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid 
• 1255651-84-3 dimethyl-2,2'-((2-(diacetoxy-λ³-iodanyl)-1,3-phenylene)bis(oxy))(2R,2'R)-dipropionate 
• 88-05-1 2,4,6-trimethylaniline 
• 1255651-99-0 (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate 
• 41046-67-7 2-iodoresorcinol 
• 108-46-3 recorcinol 

Downstream Products

• 1226896-63-4 (2,6-bis(((R)-1-(mesitylamino)-1-oxopropan-2-yl)oxy)-phenyl)-λ³-iodanediyl diacetate 

Relevant articles and documents

Enantioselective Electrochemical Lactonization Using Chiral Iodoarenes as Mediators

The enantioselective electrochemical lactonization of diketo acid derivatives using chiral iodoarenes as redox mediators is reported for the first time. Good to high stereoselectivities are observed in the lactonization and also in intermolecular α-alkoxylations of diketo ester derivatives. This enantioselective process was then adapted to an electrochemical flow microreactor where only small amounts of supporting electrolyte were necessary.

Synthesis of Polycyclic Cyclohexadienone through Alkoxy-Oxylactonization and Dearomatization of 3′-Hydroxy-[1,1′-biphenyl]-2-carboxylic Acids Promoted by Hypervalent Iodine

Alkox-oxylactonization and dearomatization of 3′-hydroxy-[1,1′-biphenyl]-2-carboxylic acid simultaneously promoted by hypervalent iodine have been developed using stoichiometric PhI(OAc)2 or a catalytic amount of chiral aryl-λ3-iodane generated in situ. This reaction provides a concise method to synthesize diverse polycyclic cyclohexadienones as potential inhibitors of DNA polymerase under mild reaction conditions.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.