115362-13-5

Basic information

• Product Name: 2,3-EPOXY-3-(4-BROMOPHENYL)-1-PROPANOL
• Synonyms: 2,3-EPOXY-3-(4-BROMOPHENYL)-1-PROPANOL
• CAS NO: 115362-13-5
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.09
• Mol File: 115362-13-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 215.8°C (rough estimate)
• Flash Point: 151.9°C
• Appearance: /
• Density: 1.4921 (rough estimate)
• Vapor Pressure: 8.08E-05mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• CAS DataBase Reference: 2,3-EPOXY-3-(4-BROMOPHENYL)-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-EPOXY-3-(4-BROMOPHENYL)-1-PROPANOL(115362-13-5)
• EPA Substance Registry System: 2,3-EPOXY-3-(4-BROMOPHENYL)-1-PROPANOL(115362-13-5)

Safety Data

• Hazardous Substances Data: 115362-13-5(Hazardous Substances Data)

Usage

General Description

2,3-EPOXY-3-(4-BROMOPHENYL)-1-PROPANOL, also known as 4-Bromophenyl glycidyl ether, is a chemical compound with the molecular formula C9H9BrO2. It is an epoxy compound containing a bromine atom and a phenyl group, and is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also used in the production of resins, adhesives, and coatings. The compound has potential health hazards and may cause skin and eye irritation upon contact, and should be handled with care in a well-ventilated area and with appropriate personal protective equipment.

InChI:InChI=1/C9H9BrO2/c10-7-3-1-6(2-4-7)9-8(5-11)12-9/h1-4,8-9,11H,5H2/t8-,9-/m1/s1

Upstream product

• 49678-04-8 4-bromocinnamaldeyde 
• 105515-33-1 (2E)-3-(4-bromophenyl)prop-2-en-1-ol 
• 49678-04-8 trans-4-bromocinnamaldehyde 
• 1020746-20-6 (2S,3R)-3-(4-bromophenyl)oxirane-2-carbaldehyde 

Downstream Products

• 1045859-10-6 (2R,3S)-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propane-1,2-diol 
• 1393810-30-4 [(8R,9S,10S)-9-(4-bromophenyl)-6-[(2-nitrophenyl)sulfonyl]-1,6-diazabicyclo[6.2.0]decan-10-yl]methanol 
• 1393810-18-8 C₄₂H₄₀BrN₃O₅S 
• 1393809-97-6 N-(((2R,3S,4S)-1-allyl-3-(4-bromophenyl)-4-((trityloxy)methyl)azetidin-2-yl)methyl)-2-nitrobenzenesulfonamide 
• 1393809-90-9 (2S,3S,4R)-1-allyl-3-(4-bromophenyl)-2-((trityloxy)methyl)azetidine-4-carbonitrile 

Relevant articles and documents

Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase

Peroxygenases are heme-dependent enzymes that use peroxide-borne oxygen to catalyze a wide range of oxyfunctionalization reactions. Herein, we report the engineering of an unusual cofactor-independent peroxygenase based on a promiscuous tautomerase that accepts different hydroperoxides (t-BuOOH and H2O2) to accomplish enantiocomplementary epoxidations of various α,β-unsaturated aldehydes (citral and substituted cinnamaldehydes), providing access to both enantiomers of the corresponding α,β-epoxy-aldehydes. High conversions (up to 98 %), high enantioselectivity (up to 98 % ee), and good product yields (50–80 %) were achieved. The reactions likely proceed via a reactive enzyme-bound iminium ion intermediate, allowing tweaking of the enzyme's activity and selectivity by protein engineering. Our results underscore the potential of catalytic promiscuity for the engineering of new cofactor-independent oxidative enzymes.

Asymmetric epoxidation of α,β-unsaturated aldehydes in aqueous media catalyzed by resin-supported peptide-containing unnatural amino acids

The enantio- and diastereoselective epoxidation of α,β- unsaturated aldehydes in aqueous media was realized using a resin-supported peptide catalyst. Introducing the hydrophobic and bulky unnatural amino acid 3-(1-pyrenyl)alanine into the peptide sequence was effective for enhancing the reaction rate and enantioselectivity.

Amine-catalyzed asymmetric epoxidation of α,β-unsaturated aldehydes

The direct organocatalytic enantioselective epoxidation of α,β-unsaturated aldehydes with different peroxides is presented. Proline, chiral pyrrolidine derivatives, and amino acid-derived imidazolidinones catalyze the asymmetric epoxidation of α,β-unsatur