94386-29-5

Basic information

• Product Name: 5-bromodihydrofuran-2(3H)-one
• Synonyms: 5-bromodihydrofuran-2(3H)-one;5-Bromo-4,5-dihydrofuran-2(3H)-one
• CAS NO: 94386-29-5
• Molecular Formula: C₄H₅BrO₂
• Molecular Weight: 164.9853
• EINECS: 305-251-2
• Mol File: 94386-29-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 260.685 °C at 760 mmHg
• Flash Point: 111.459 °C
• Appearance: /
• Density: 1.821 g/cm³
• Vapor Pressure: 0.0121mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: 5-bromodihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromodihydrofuran-2(3H)-one(94386-29-5)
• EPA Substance Registry System: 5-bromodihydrofuran-2(3H)-one(94386-29-5)

Safety Data

• Hazardous Substances Data: 94386-29-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 419, 1978 DOI: 10.1016/S0040-4039(01)91443-1

InChI:InChI=1/C4H5BrO2/c5-3-1-2-4(6)7-3/h3H,1-2H2

Upstream product

• 96-48-0 4-butanolide 

Downstream Products

• 180037-65-4 γ-(2-naphthyl)-γ-butyrolactone 
• 1068969-42-5 2-phenyl-pyrimidine-5-carboxylic acid [4-(2-oxo-tetrahydro-furan-3-yl)-piperazin-1-yl]-amide 

Relevant articles and documents

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.