20697-03-4

Basic information

• Product Name: 2-(3-methylphenyl)oxirane
• Synonyms: 2-(3-methylphenyl)oxirane;(3-Methylphenyl)oxirane;3-Methylstyrene oxide;Brn 1281584;Ccris 1156;m-(Epoxyethyl)toluene;m-Methylstyrene oxide;Oxirane, (3-methylphenyl)- (9ci)
• CAS NO: 20697-03-4
• Molecular Formula: C9H10O
• Molecular Weight: 134.1751
• Mol File: 20697-03-4.mol
• Article Data: 48

Chemical Properties

• Boiling Point: 214.5°Cat760mmHg
• Flash Point: 78.5°C
• Appearance: /
• Density: 1.075g/cm³
• Vapor Pressure: 0.226mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 2-(3-methylphenyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-methylphenyl)oxirane(20697-03-4)
• EPA Substance Registry System: 2-(3-methylphenyl)oxirane(20697-03-4)

Safety Data

• Hazardous Substances Data: 20697-03-4(Hazardous Substances Data)

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

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.