99528-63-9

Basic information

• Product Name: [(2S,3R)-3-phenyloxiran-2-yl]methanol
• Synonyms: 2-Oxiranemethanol, 3-phenyl-, (2S,3R)-
• CAS NO: 99528-63-9
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Mol File: 99528-63-9.mol
• Article Data: 119

Chemical Properties

• Boiling Point: 277.5°C at 760 mmHg
• Flash Point: 129.5°C
• Density: 1.182g/cm³
• Vapor Pressure: 0.00217mmHg at 25°C
• Refractive Index: 1.567
• PKA: 14.44±0.10(Predicted)
• CAS DataBase Reference: [(2S,3R)-3-phenyloxiran-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,3R)-3-phenyloxiran-2-yl]methanol(99528-63-9)
• EPA Substance Registry System: [(2S,3R)-3-phenyloxiran-2-yl]methanol(99528-63-9)

Safety Data

• Hazardous Substances Data: 99528-63-9(Hazardous Substances Data)

Upstream product

• 104-54-1 3-Phenylpropenol 
• 100-52-7 benzaldehyde 
• 57813-28-2 β-hydroxyethyltriphenylarsonium bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 3071-32-7 (S)-(-)-(1-phenyl)ethylhydroperoxide 
• 67-56-1 methanol 
• 104-55-2 3-phenyl-propenal 
• 71403-94-6 2,3-epoxy-3-phenylpropanal 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 536-74-3 phenylacetylene 
• 21915-53-7 2,3-epoxy-3-phenyl-1-propanol 
• 58210-04-1 (+)-(1S,2S)-2-(dimethylamino)-1-phenylpropane-1,3-diol 

Downstream Products

• 99528-65-1 (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate 
• 110379-48-1 (R)-(R)-[1,3]Dioxolan-4-yl-phenyl-methanol 
• 114395-16-3 [(2S,3S)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 121958-41-6 [(2R,3R)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 57200-23-4 3-phenyl-2(5H)-furanone 
• 129266-26-8 2-C-(2,5-dihydro-2-oxo-3-phenylfur-5-yl)lactic acid 
• 129266-27-9 (S)-2-Hydroxy-2-((S)-5-oxo-4-phenyl-2,5-dihydro-furan-2-yl)-propionic acid methyl ester 
• 4982-08-5 1-hydroxy-3-phenylpropan-2-one 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 19881-97-1 3-phenylpropane-1,2-diol 
• 60633-79-6 1-bromo-3-phenyl-2-epoxypropane 
• 132560-49-7 2-Iodomethyl-3-phenyl-oxirane 
• 121802-31-1 (S)-4-((S)-Hydroxy-phenyl-methyl)-[1,3]dioxolan-2-one 
• 121844-57-3 (4S,5S)-4-Hydroxymethyl-5-phenyl-[1,3]dioxolan-2-one 

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.

Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

Efficient and selective oxidation of alcohols to carbonyl compounds at room temperature by a ruthenium complex catalyst and hydrogen peroxide

In this study, convenient and selective oxidation of alcohols using aqueous hydrogen peroxide to yield carbonyl compounds was studied. Using the ruthenium-(4-methylphenyl-2,6-bispydinyl) pyridinedicarboxylate complex [Ru(mpbp)(pydic)] as a catalyst, primary and secondary alcohols were oxidized to aldehydes and ketones at room temperature with a satisfactory yield and excellent selectivity. The influence of various reaction parameters, such as solvent, catalyst and oxidant amount on both the activity and selectivity was also evaluated. Kinetic studies showed that the oxidation of alcohol was first order in terms of the substrate and hydrogen peroxide, and was second order in terms of the catalyst. A plausible mechanism involving ruthenium-oxo species with electrophilic character was proposed based on the in situ UV-vis spectroscopy studies and Hammett plots.