20697-03-4

Usage

General Description

2-(3-methylphenyl)oxirane, also known as 3-methylphenyl glycidyl ether, is a chemical compound with the molecular formula C9H10O. It is an epoxide, which is a cyclic ether with a three-membered ring, also known as an oxirane. 2-(3-methylphenyl)oxirane is a colorless to light yellow liquid with a sweet, floral odor. It is commonly used as a raw material in the production of various chemical compounds, including pharmaceuticals, pesticides, and flavor and fragrance ingredients. It is also used as a solvent and as an intermediate in organic synthesis. 2-(3-methylphenyl)oxirane is considered to be toxic and may cause irritation to the skin, eyes, and respiratory system, and should be handled with caution in a well-ventilated area.

InChI:InChI=1/C9H10O/c1-7-3-2-4-8(5-7)9-6-10-9/h2-5,9H,6H2,1H3

Upstream product

• 2181-42-2 trimethylsulphonium iodide 
• 620-23-5 m-tolyl aldehyde 
• 100-80-1 3-methylstyrene 
• 704898-29-3 3-methylstyrene oxide 
• 65-85-0 benzoic acid 
• 6814-64-8 methylenedimethyl sulfurane 
• 2181-44-4 trimethylsulfonium methylsulfate 

Downstream Products

• 1166859-59-1 (R)-3-(3-methylphenyl)-1,2-thiazolidine 1,1-dioxide 
• 1166859-52-4 3-(3-methylphenyl)-4,5-dihydro-isothiazole 1,1-dioxide 
• 1426257-38-6 (E)-1-methyl-3-(2-(phenylsulfonyl)vinyl)benzene 
• 1313709-37-3 trans-(3-methyl)-1-phenylthiostyrene 

Relevant academic research and scientific papers

A new clade of styrene monooxygenases for (R)-selective epoxidation

Styrene monooxygenases (SMOs) are excellent enzymes for the production of (S)-enantiopure epoxides, but so far, only one (R)-selective SMO has been identified with a narrow substrate spectrum. Mining the NCBI non-redundant protein sequences returned a new distinct clade of (R)-selective SMOs. Among them,SeStyA fromStreptomyces exfoliatus,AaStyA fromAmycolatopsis albispora, andPbStyA fromPseudonocardiaceaewere carefully characterized and found to convert a spectrum of styrene analogues into the corresponding (R)-epoxides with up to >99% ee. Moreover, site 46 (AaStyA numbering) was identified as a critical residue that affects the enantioselectivity of SMOs. Phenylalanine at site 46 was required for the (R)-selective SMO to endow excellent enantioselectivity. The identification of new (R)-selective SMOs would add a valuable green alternative to the synthetic tool box for the synthesis of enantiopure (R)-epoxides.

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

Aerobic epoxidation of olefins by carboxylate ligand-based cobalt (II) compound: synthesis, X-ray crystallography, and catalytic exploration

A new quinoline carboxylate-based cobalt (II) metal compound, [Co (HL1)2(H2O)4] (1) (H2L1 = 2-hydroxyquinoline-4-carboxylic acid) has been hydrothermally synthesized, and fully characterized by single-crystal X-ray diffraction, powder X-ray diffraction, Fourier-transform infrared (FT-IR), elemental and thermo-gravimetric analysis. Compound 1 shows high thermal stability up to ~300°C. Single-crystal X-ray diffraction study of 1 exhibited monomeric structure experiences further stabilized in solid state through different non-covalent interaction, for example, H-bonding and π···π stacking interaction and extended to 3D supramolecular H-bonded network. Compound 1 efficiently catalyzes epoxidation reactions of olefins under homogeneous conditions using molecular oxygen as an oxidizer. Another reported quinoline carboxylate-based nickel (II) monomer [Ni(L2)2(H2O)2] (2) (HL2 = thiazole-4-carboxylic acid) has been synthesized and characterized to compare it with compound 1 towards aerobic epoxidation reactions, where 1 comes as superior.

Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides

A Ni/photoredox-catalyzed enantioselective reductive coupling of styrene oxides and aryl iodides is reported. This reaction affords access to enantioenriched 2,2-diarylalcohols from racemic epoxides via a stereoconvergent mechanism. Multivariate linear regression (MVLR) analysis with 29 bioxazoline (BiOx) and biimidazoline (BiIm) ligands revealed that enantioselectivity correlates with electronic properties of the ligands, with more electron-donating ligands affording higher ee's. Experimental and computational mechanistic studies were conducted, lending support to the hypothesis that reductive elimination is enantiodetermining and the electronic character of the ligands influences the enantioselectivity by altering the position of the transition state structure along the reaction coordinate. This study demonstrates the benefits of utilizing statistical modeling as a platform for mechanistic understanding and provides new insight into an emerging class of chiral ligands for stereoconvergent Ni and Ni/photoredox cross-coupling.

Kinetic resolution ofN-aryl β-amino alcoholsviaasymmetric aminations of anilines

An efficient kinetic resolution ofN-aryl β-amino alcohols has been developedviaasymmetricpara-aminations of anilines with azodicarboxylates enabled by chiral phosphoric acid catalysis. Broad substrate scope and high kinetic resolution performances were afforded with this method. Control experiments supported the critical roles of the NH and OH group in these reactions.

MeOTf/KI-catalyzed efficient synthesis of 2-arylnaphthalenesviacyclodimerization of styrene oxides

The MeOTf/KI-catalyzed synthesis of 2-arylnaphthalene derivatives from aryl ethylene oxides in alcohol under ambient conditions is described. The present protocol has a higher atom efficiency and wider substrate applicability with excellent yields. The reaction proceeded using the aryl ethylene oxides to give 2-arylnaphthalenes either in homo-coupling or in cross-coupling. The reaction could also be carried out at the gram scale in minutes.

Oxidovanadium(V) and dioxidomolybdenum(VI) Complexes of N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-fluorobenzohydrazide: Synthesis, characterization, crystal structures and catalytic property

N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-fluorobenzohydrazide (H2L) was used to prepare oxidovanadium(V) complex [VOL(OEt)(MeOH)] (1) and dioxidomolybdenum(VI) complex [MoO2L(OH2)]·[MoO2L(EtOH)] (2). The complexes were characterized by IR, UV-Vis, NMR spectroscopy, and single crystal X-ray diffraction. X-ray analysis indicates that the complexes are mononuclear species with the metal atoms in octahedral coordination. The complexes were studied for catalytic oxidation property on some olefins with tert-butyl hydroperoxide as oxidant.

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.

Photoenzymatic epoxidation of styrenes

Two-component-diffusible-flavomonooxygenases are versatile biocatalysts for selective epoxidation-, hydroxylation- or halogenation reactions. Their complicated molecular architecture can be simplified using photochemical regeneration of the catalytically

Synthesis, Characterization and Crystal Structures of Oxidovanadium(V) and Dioxidomolybdenum(VI) Complexes Derived from 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide with Catalytic Property

Abstract: A hydrazone compound 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H2L) was prepared and characterized by IR, UV-Vis and NMR spectra. Based on the hydrazone compound, a new oxidovanadium(V) and a new dioxidomolybdenum(VI) complexes, [VO(L)(OEt)(EtOH)] (I) and [MoO2(L)(OH2)] (II), were prepared and characterized by IR, UV-Vis, NMR spectra, and single crystal X-ray diffraction (CIF files nos. 1866755 (I) and 1866756 (II)). Complex I crystallizes as the monoclinic space group P21/c with unit cell dimensions a = 12.8733(12), b = 13.5088(13), c = 11.9262(11) ?, β = 91.765(2)°, V = 2073.0(3) ?3, Z = 4, R1 = 0.0524, wR2 = 0.1329, GOOF = 1.245. Complex II crystallizes as the monoclinic space group P21/c with unit cell dimensions a = 8.1140(9), b = 16.2975(19), c = 13.4318(15) ?, β = 106.456(2)°, V = 1703.4(3) ?3, Z = 4, R1 = 0.0296, wR2 = 0.0728, GOOF = 1.046. X-ray analysis indicates that the complexes are mononuclear species with the metal atoms in octahedral coordination. The complexes were studied for catalytic oxidation property on some olefins with tert-butyl hydrogen peroxide as oxidant.