403501-35-9

Basic information

• Product Name: (R)-(3-Fluorophenyl)oxirane
• Synonyms: (R)-(3-Fluorophenyl)oxirane;(R)-3-Fluorostyrene oxide;(R)-2-(3-Fluorophenyl)oxirane
• CAS NO: 403501-35-9
• Molecular Formula: C₈H₇FO
• Molecular Weight: 138.1389832
• Mol File: 403501-35-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(3-Fluorophenyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(3-Fluorophenyl)oxirane(403501-35-9)
• EPA Substance Registry System: (R)-(3-Fluorophenyl)oxirane(403501-35-9)

Safety Data

• Hazard Codes: T
• Statements: 45-21-36
• Safety Statements: 53-26-36/37-45
• Hazardous Substances Data: 403501-35-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(R)-(3-Fluorophenyl)oxirane is used as a reagent in the Bronsted acid-catalyzed enantioselective conversion of epoxides to thiiranes. This application is significant because it allows for the selective synthesis of chiral thiiranes, which are important building blocks in the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(3-Fluorophenyl)oxirane is used as a key intermediate in the synthesis of various chiral drugs. Its unique R-configuration and reactivity make it a valuable component in the development of new drugs with improved efficacy and selectivity.
Used in Research and Development:
(R)-(3-Fluorophenyl)oxirane is also utilized in research and development for the study of enantioselective reactions and the development of new catalytic systems. Its use in these areas contributes to the advancement of synthetic chemistry and the discovery of novel compounds with potential applications in various fields.

Upstream product

• 350-51-6 3-fluorostyrene 
• 18511-63-2 3-fluorophenylethylene oxide 
• 456-48-4 3-Fluorobenzaldehyde 
• 1446417-85-1 (R)-2-bromo-1-(3-fluorophenyl)ethan-1-ol 

Relevant articles and documents

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.

FLUOROPHENYL BETA-HYDROXYETHYLAMINES AND THEIR USE IN THE TREATMENT OF HYPERGLYCAEMIA

There is herein provided a compound of formula (I).

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Catalytic Enantioselective Conversion of Epoxides to Thiiranes

A highly efficient and enantioselective Br?nsted acid catalyzed conversion of epoxides to thiiranes has been developed. The reaction proceeds in a kinetic resolution, furnishing both epoxide and thiirane in high yields and enantiomeric purity. Heterodimer formation between the catalyst and sulfur donor affords an effective way to prevent catalyst decomposition and enables catalyst loadings as low as 0.01 mol %.

Lithiated fluorinated styrene oxides: Configurational stability, synthetic applications, and mechanistic insight

The configurational stability of some lithiated fluorinated styrene oxides has been investigated. Chemical studies have shown that in ethereal solvents α-lithiated ortho-, meta-, and para-fluorostyrene oxides (2-Li, α-5-Li, and α-6-Li) are all configurationally stable in the reaction time scale, whereas a-lithiated ortho-, meta-, and paratrifluoromethylstyrene oxides (9-Li, 13-Li, and 14-Li) are configurationally unstable. Optically active oxiranyllithiums 2-Li and 9-Li, could be stereospecifically generated and quenched with electrophiles. The corresponding derivatives were then successfully subjected to regiospecific ring-opening reactions with amines to give fluorinated ssamino alcohols with a stereodefined quaternary carbinol center, which are useful synthons in medicinal chemistry. The barriers of inversion have been calculated (Eyring equation) for oxiranyllithiums 9-Li, 13-Li, and 14-Li by determining the enantiomeric ratios after electrophilic quenching on aging the enantioenriched organolithium for different times in THF; in the case of 9-Li, activation parameters have also been determined. Mechanisms that may be responsible of the racemization oxiranyllithiums 9-Li, 13-Li, and 14-Li undergo once generated are also discussed.

A Unique Binaphthyl Strapped Iron-Porphyrin Catalyst for the Enantioselective Epoxidation of Terminal Olefins

A new chiral binaphthyl-strapped iron-porphyrin 4b that exhibits unprecedented catalytic activity toward the enantioselective epoxidation of terminal olefins was synthesized. Typical enantiomeric excesses (ee) of 90% were measured with a maximum of 97% fo

Electronic effects on enantioselectivity in epoxidation catalyzed by D 4-symmetric chiral porphyrins

Asymmetric epoxidation of various aromatic olefins was examined with our D4-symmetric chiral porphyrin. The enantioselectivity was greatly improved upon when the substrates contained electron-deficient groups. Moreover, examination of electroni