63017-57-2

Basic information

• Product Name: (prop-1-en-2-ylselanyl)benzene
• CAS NO: 63017-57-2
• Molecular Formula: C₉H₁₀Se
• Molecular Weight: 197.1357
• Mol File: 63017-57-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 229.1°C at 760 mmHg
• Flash Point: 92.4°C
• Vapor Pressure: 0.107mmHg at 25°C
• CAS DataBase Reference: (prop-1-en-2-ylselanyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (prop-1-en-2-ylselanyl)benzene(63017-57-2)
• EPA Substance Registry System: (prop-1-en-2-ylselanyl)benzene(63017-57-2)

Safety Data

• Hazardous Substances Data: 63017-57-2(Hazardous Substances Data)

Usage

General Description

(prop-1-en-2-ylselanyl)benzene, also known as allylphenyl selenide, is an organoselenium compound with the molecular formula C9H10Se. It is a colorless to pale yellow liquid with a pungent, garlic-like odor. (prop-1-en-2-ylselanyl)benzene is used as a reagent in organic synthesis and is known for its potential medical applications, particularly in relation to its antioxidant and anti-inflammatory properties. It has been explored for its potential in the treatment of various diseases, including cancer. However, the compound should be handled with caution as it is considered to be toxic and may have harmful effects on human health if not used properly.

Upstream product

• 1666-13-3 diphenyl diselenide 
• 34837-55-3 Phenylselenyl bromide 
• 66030-49-7 phenyl vinyl selenoxide 
• 74-88-4 methyl iodide 
• 35167-28-3 vinyl phenyl selenide 
• 63017-63-0 (1-Bromo-1-methyl-ethylselanyl)-benzene 
• 35446-87-8 2,2-bis (phenylseleno)propane 
• 38447-66-4 acetyl phenyl selenide 
• 13291-18-4 isopropenylmagnesium bromide 

Downstream Products

• 115476-70-5 3-Chloro-5-methyl-2-oxo-5-phenylselanyl-tetrahydro-furan-3-carbonitrile 
• 115476-65-8 3,3-Dichloro-5-methyl-5-phenylselanyl-dihydro-furan-2-one 
• 115476-80-7 5-Methyl-2-oxo-5-phenylselanyl-tetrahydro-furan-3-carbonitrile 
• 148249-65-4 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-phenylselanyl-pent-4-enoic acid methyl ester 
• 148249-67-6 tert-Butyl-dimethyl-[(R)-3-methyl-1-(2-phenylselanyl-allyl)-but-2-enyloxy]-silane 
• 115476-63-6 phenyl isopropenyl selenoxide 
• 148249-47-2 methyl (R)-2-hydroxy-4-(phenylselanyl)pent-4-enoate 

Relevant articles and documents

Bisannelation with vinylselenoxide: Synthesis of tricyclo[3.2.1.0(2,7)]octane-6-one and its Congeners

Reaction of kinetic enolate of α'-substituted cyclohexenone derivatives with vinylselenoxides provided tricyclo[3.2.1.0(2,7)]octane-6-one derivatives via domino Michael-Michael-substitution protocol. (C) 2000 Elsevier Science Ltd.

Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues

A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.