78619-09-7

Basic information

• Product Name: 1-vinylbenzene-3,4-oxide
• Synonyms: 1-vinylbenzene-3,4-oxide;3-Vinyl-7-oxabicyclo[4.1.0]hepta-2,4-diene
• CAS NO: 78619-09-7
• Molecular Formula: C₈H₈O
• Molecular Weight: 0
• Mol File: 78619-09-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 192°C at 760 mmHg
• Flash Point: 63.6°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 0.697mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: 1-vinylbenzene-3,4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-vinylbenzene-3,4-oxide(78619-09-7)
• EPA Substance Registry System: 1-vinylbenzene-3,4-oxide(78619-09-7)

Safety Data

• Hazardous Substances Data: 78619-09-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8O/c1-2-6-3-4-7-8(5-6)9-7/h2-5,7-8H,1H2

Upstream product

• 81498-78-4 4,5-dibromo-4-(2-bromoethyl)cyclohexane-1,2-oxide 
• 71647-37-5 1-(2'-hydroxyethyl)-1,4-cyclohexadiene 
• 82296-88-6 4,5-dibromo-4-(2-bromoethyl)-1-cyclohexene 

Downstream Products

• 70201-86-4 1-(ethylsulfanyl)-2-vinylbenzene 
• 2628-17-3 4-Vinylphenol 
• 1204504-31-3 C₁₄H₁₇NO₃S 
• 1204504-28-8 3-vinylphenylmercapturic acid 
• 510769-03-6 4-vinylphenylmercapturic acid 

Relevant articles and documents

New urinary metabolites formed from ring-oxidized metabolic intermediates of styrene

The urine from mice exposed to styrene vapors (600 and 1200 mg/m 3, 6 h) was analyzed for ring-oxidized metabolites of styrene. To facilitate the identification of metabolites in urine, the following potential metabolites were prepared: 2-, 3-, and 4-vinylphenol (2-, 3-, and 4-VP), 4-vinylpyrocatechol, and 2-, 3-, and 4-vinylphenylmercapturic acid (2-, 3-, and 4-VPMA). For the analysis of vinylphenols β-glucuronidase-treated urine was extracted and derivatized with acetanhydride/triethylamine before injection into GC/MS. Three isomers, 2-, 3-, and 4-VP, were found in the exposed urine using authentic standards. Additionally, three novel minor urinary metabolites, arylmercapturic acids 2-, 3-, and 4-VPMA, were identified by LC-ESI-MS 2 by comparison with authentic standards. Excretion of the most abundant isomer, 4-VPMA, amounted to 535 ± 47 nmol/kg and 984 ± 78 nmol/kg, representing approximately 0.047 and 0.043% of the absorbed dose for the exposure levels of 600 and 1200 mg/m3, respectively. The ratio of 2-VPMA, 3-VPMA, and 4-VPMA was approximately 2:1:6. In model reactions of styrene 3,4-oxide (3,4-STO) with N-acetylcysteine in aqueous solutions and of its methyl ester in methanol, 4-vinylphenol was always the main product, while 3-vinylphenol has never been detected. No mercapturic acid was found in the reaction of 3,4-STO with N-acetylcysteine in aqueous solution at pH 7.4 or 9.7, but a small amount of 4-VPMA methyl ester was detected by LC-ESI-MS after the reaction of 3,4-STO with N-acetylcysteine methyl ester. In contrast, no mercapturic acid was found in the reaction of 3,4-STO with N-acetylcysteine in aqueous solution at pH 7.4 or 9.7. These findings indicate a capability of 3,4-STO to react with cellular thiol groups despite its rapid isomerization to vinylphenol in an aqueous environment. Moreover, the in vivo formation of 2- and 3-isomers of both VP and VPMA, neither of which was formed from 3,4-STO in vitro, strongly suggests that another arene oxide, styrene 2,3-oxide, might be a minor metabolic intermediate of styrene.