188539-86-8

Basic information

• Product Name: (R)-1-bromo-3-(methylsulfinyl)benzene
• Synonyms: (R)-1-bromo-3-(methylsulfinyl)benzene
• CAS NO: 188539-86-8
• Molecular Weight: 219.102
• Mol File: 188539-86-8.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (R)-1-bromo-3-(methylsulfinyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-bromo-3-(methylsulfinyl)benzene(188539-86-8)
• EPA Substance Registry System: (R)-1-bromo-3-(methylsulfinyl)benzene(188539-86-8)

Safety Data

• Hazardous Substances Data: 188539-86-8(Hazardous Substances Data)

Usage

Description

(R)-1-bromo-3-(methylsulfinyl)benzene, with the molecular formula C7H7BrS, is a chiral chemical compound that exists in two enantiomers, (R) and (S), which are mirror images of each other. (R)-1-bromo-3-(methylsulfinyl)benzene is significant in the field of chemistry and chemical synthesis due to its versatile applications.

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(R)-1-bromo-3-(methylsulfinyl)benzene is utilized as a building block in the preparation of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a wide range of biologically active molecules, making it a valuable asset in the development of new drugs and agricultural products.
Used in Organic Synthesis as a Reagent:
(R)-1-bromo-3-(methylsulfinyl)benzene serves as a reagent for the synthesis of chiral sulfoxides and sulfides, which are important structural motifs in many biologically active molecules. The presence of the chiral center in (R)-1-bromo-3-(methylsulfinyl)benzene enables the production of enantiomerically pure compounds, which is crucial for the effectiveness and safety of pharmaceuticals.
Used in the Development of New Materials:
(R)-1-bromo-3-(methylsulfinyl)benzene has potential applications in the development of new materials, thanks to its unique chemical properties and reactivity. This makes it a promising candidate for research and innovation in material science.
Used as a Precursor for Chiral Ligands in Asymmetric Catalysis:
In the field of organic synthesis, (R)-1-bromo-3-(methylsulfinyl)benzene is also used as a precursor for the preparation of chiral ligands for asymmetric catalysis. These ligands play a vital role in enhancing the selectivity and efficiency of various chemical reactions, leading to the production of enantiomerically enriched products.

Upstream product

• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 29959-92-0 1-bromo-3-methanesulfinyl-benzene 

Relevant articles and documents

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Stereoselective sulfoxidation catalyzed by achiral Schiff base complexes in the presence of serum albumin in aqueous media

Four coordination complexes ML derived from an achiral Schiff base ligand (H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol) have been synthesized and characterized. A method is described for the enantioselective oxidation of a series of aryl alkyl sulfides using the coordination complexes in the presence of serum albumins (SAs) in an aqueous medium at ambient temperature. The mixture of metal complexes with serum albumins is useful for inducing asymmetric catalysis. The complex, albumin source and substrate influence stereoselective sulfoxidation. At optimal pH with the appropriate oxidant, some of ML/SA systems are identified as very efficient catalysts, giving the corresponding sulfoxides in excellent chemical yield (up to 100%) and good enantioselectivity (up to 94% ee) in certain cases. UV–visible spectroscopic data provide evidence that stronger binding between the complex and serum albumin lead to higher enantioselectivity.

Efficient HPLC enantiomer separation using a pillared homochiral metal-organic framework as a novel chiral stationary phase

HPLC enantioseparation of racemates using novel pillared homochiral metal-organic framework-silica composite as chiral stationary phase has been successfully demonstrated.