71031-03-3

Basic information

• Product Name: (S)-2-Oxiranylanisole
• Synonyms: (S)-2-OXIRANYLANISOLE;(S)-GLYCIDYL PHENYL ETHER;(S)-ALPHA-(2-OXIRANYL)ANISOLE;SPGE;(S)-PHENYL GLYCIDYL ETHER;OXIRANE, (PHENOXYMETHYL)-, (2S)-;(2S)-1,2-EPOXY-3-PHENOXYPROPANE;(S)-α-(2-Oxiranyl)anisole, (S)-Glycidyl phenyl ether
• CAS NO: 71031-03-3
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Mol File: 71031-03-3.mol
• Article Data: 92

Chemical Properties

• Flash Point: 71 °C
• Appearance: /
• Density: 1.11
• Refractive Index: 1.5290-1.5330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (S)-2-Oxiranylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Oxiranylanisole(71031-03-3)
• EPA Substance Registry System: (S)-2-Oxiranylanisole(71031-03-3)

Safety Data

• Hazard Codes: T
• Statements: 45-20/21-37/38-41-43-52/53-68
• Safety Statements: 53-26-36/37/39-45-61
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 71031-03-3(Hazardous Substances Data)

Usage

General Description

The epoxide hydrolase isolated from Bacillus megaterium ECU1001 can preferentially hydrolyze the (R)-enantiomer of racemic phenyl glycidyl ether to yield optically pure (S)-phenyl glycidyl ether.

InChI:InChI=1/C9H10O2/c1-10-8-5-3-2-4-7(8)9-6-11-9/h2-5,9H,6H2,1H3/t9-/m1/s1

Upstream product

• 140630-45-1 (R)-1-chloro-3-phenoxy-2-propanol 
• 108-95-2 phenol 
• 122-60-1 Phenyl glycidyl ether 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 67843-74-7 (S)-epichlorohydrin 
• 113826-06-5 (R)-glycidyl tosylate 
• 106-89-8 epichlorohydrin 
• 4248-19-5 tert-butyl carbazate 
• 621-84-1 O-benzyl carbamate 
• 51-79-6 urethane 
• 70987-78-9 (S)-Glycidyl tosylate 
• 100-51-6 benzyl alcohol 
• 140630-40-6 Acetic acid (R)-1-bromomethyl-2-phenoxy-ethyl ester 
• 1746-13-0 allyl phenyl ether 

Downstream Products

• 15288-08-1 1-diethylamino-3-phenoxy-propan-2-ol 
• 890017-17-1 4-((S)-2-hydroxy-3-phenoxy-propylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 202414-94-6 (S)-4-phenoxy-3-hydroxybutanoic acid methyl ester 
• 355414-97-0 (2S)-1-phenoxy-3-[N-benzyl-3,3-bis[3-(methoxycarbonylamino)phenyl]propylamino]-2-propanol 

Relevant articles and documents

An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst

An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).

Engineering a homochiral metal-organic framework based on an amino acid for enantioselective separation

A chiral metal-organic framework possessing an open amphiphilic channel is constructed from a dicarboxylate ligand derived from an amino acid and is shown to be an efficient and recyclable chiral solid adsorbent, which is capable of separating racemic secondary alcohols, epoxides, and ibuprofen with very high enantioselectivity.

Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium

A gene encoding halohydrin dehalogenase from an alphaproteobacterium (AbHHDH) was identified, cloned and over-expressed in Escherichia coli. AbHHDH was able to catalyze the stereoselective dehalogenation of prochiral and racemic halohydrins. It showed the highest enantioselectivity in the dehalogenation of 20?mM (R,S)-2-bromo-1-phenylethanol, which yielded (S)-2-bromo-1-phenylethanol with 99% ee and 34.5% yield. Moreover, AbHHDH catalyzed the azidolysis of epoxides with low to moderate (S)-enantioselectivity. The highest enantioselectivity (E = 18.6) was observed when (R,S)-benzyl glycidyl ether was used as the substrate. A sequential kinetic resolution catalyzed by HHDH was employed for the synthesis of chiral 1-chloro-3-phenoxy-2-propanol. We prepared enantiopure (S)-isomer with a high enantiopurity of ee > 99% and a yield of 30.7% (E-value: 21.3) by kinetic resolution of 20?mM substrate. The (S)-isomer with 99% ee readily obtained from 40 to 150?mM (R,S)-1-chloro-3-phenoxy-2-propanol. Taken together, the results of this study demonstrate the applicability of this HHDH for the production of optically active compounds. [Figure not available: see fulltext.].