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
• Article Data: 7

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

(R)-(3-Fluorophenyl)oxirane is a useful reagent in the bronsted acid catalyzed enantioselective conversion of epoxides to thiiranes.

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.

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.

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.