6452-72-8

Basic information

• Product Name: [[o-(allyloxy)phenoxy]methyl]oxirane
• Synonyms: [[o-(allyloxy)phenoxy]methyl]oxirane;1-(ALLYLOXY)-2-(2,3-EPOXYPROPXY)BENZENE;2-[[2-(2-Propenyloxy)phenoxy]methyl]oxirane;[[2-(2-Propenyloxy)phenoxy]methyl]oxirane
• CAS NO: 6452-72-8
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.23776
• EINECS: 229-258-4
• Mol File: 6452-72-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 305.1°C at 760 mmHg
• Flash Point: 101.7°C
• Appearance: /
• Density: 1.109g/cm³
• Vapor Pressure: 0.00151mmHg at 25°C
• Refractive Index: 1.53
• Solubility: Dichloromethane
• CAS DataBase Reference: [[o-(allyloxy)phenoxy]methyl]oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: [[o-(allyloxy)phenoxy]methyl]oxirane(6452-72-8)
• EPA Substance Registry System: [[o-(allyloxy)phenoxy]methyl]oxirane(6452-72-8)

Safety Data

• Hazardous Substances Data: 6452-72-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

An intermediate in the preparation of a β-Adrenergic blocker.

InChI:InChI=1/C12H14O3/c1-2-7-13-11-5-3-4-6-12(11)15-9-10-8-14-10/h2-6,10H,1,7-9H2

Upstream product

• 106-89-8 epichlorohydrin 
• 1126-20-1 2-allyloxyphenol 
• 118712-54-2 glycidyl p-toluenesulfonate 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 131813-15-5 N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-allyloxyphenoxy)propanamine hydrochloride 
• 133154-82-2 6-[2-[2-[3-(2-Allyloxy-phenoxy)-2-hydroxypropylamino]ethyl]benzimidazol-5-yl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 66966-19-6 (R)-1-(2'-allyloxyphenoxy)-2,3-epoxypropane 
• 66901-82-4 (R)-2-allyloxy-1-(2,3-dihydroxypropoxy)benzene 
• 58756-97-1 1-(2-allyloxy-phenoxy)-3-[2-(3-methyl-pyrazin-2-yloxy)-ethylamino]-propan-2-ol 
• 133154-70-8 6-[3-[2-[3-(2-Allyloxy-phenoxy)-2-hydroxypropylamino]ethoxy]phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 133154-61-7 6-[4-[2-[3-(2-Allyloxy-phenoxy)-2-hydroxypropylamino]ethoxy]phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone 
• 133177-63-6 6-[2-[2-[3-(2-Allyloxy-phenoxy)-2-hydroxypropylamino]ethyl]benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone 
• 66817-28-5 N-({2-[3-(2-Allyloxy-phenoxy)-2-hydroxy-propylamino]-ethylcarbamoyl}-methyl)-4-chloro-benzamide 
• 6452-71-7 oxprenolol 
• 6452-54-6 3--1,2-propanediol 
• 58827-33-1 Furan-2-carboxylic acid {2-[3-(2-allyloxy-phenoxy)-2-hydroxy-propylamino]-ethyl}-amide 
• 101532-61-0 5-{[3-(2-Allyloxy-phenoxy)-2-hydroxy-propyl]-methyl-amino}-2-(3,4-dimethoxy-phenyl)-2-isopropyl-pentanenitrile 
• 59613-89-7 1-(2-Allyloxy-phenoxy)-3-{6-[3-(2-allyloxy-phenoxy)-2-hydroxy-propylamino]-hexylamino}-propan-2-ol 

Relevant articles and documents

A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors

Microtuning of the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward bulky substrates. Hot pockets: Microtuning of the enzyme active pocket gives a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots, and enhanced activity toward bulky substrates was found.

Determination of the enantiomeric purity and the configuration of β- aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: Application to β-blockers

A method has been developed for determining the enantiomeric purity and the absolute configuration of β-aminoalcohols of type ArOCH2CH(OH)CH2NHR (R = iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The 19F NMR analysis of the derivative obtained revealed the presence of two distinctly separate signals (~2.5 ppm), the one for the RS-SR pair being the most deshielded. The configuration was determined directly on the aminoalcohol by using the acid. In stoichiometric conditions, when R = iPr, the amide function was obtained very preponderantly. The 19F NMR spectrum of the amide presented four distinct signals when derivatization was carried out by means of a reaction between the (±)-β-aminoalcohol and the (R)-AFPA. The extreme signals, which were over 3.5 ppm apart, did not belong to the same diastereomer. With R = tBu essentially the ester function was obtained. The first studies revealed the presence of two signals, though not as clearly separated as in the previous cases. Each experiment was simple to perform, and purification was not necessary. Mosher's acid gave unsatisfactory results in each case. (C) 2000 Elsevier Science Ltd.