5296-64-0

Basic information

• Product Name: ALLYL PHENYL SULFIDE
• Synonyms: ALLYL PHENYL SULFIDE;ALLYL PHENYL SULPHIDE;(Allylsulfanyl)benzene;(Allylthio)benzene;3-(Phenylthio)prop-1-ene;3-(Phenylthio)propene;Allyl phenyl thioether;Benzene, (2-propenylthio)-
• CAS NO: 5296-64-0
• Molecular Formula: C₉H₁₀S
• Molecular Weight: 150.24
• EINECS: 226-142-5
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 5296-64-0.mol
• Article Data: 132

Chemical Properties

• Melting Point: -48--46.5 °C
• Boiling Point: 223-225 °C(lit.)
• Flash Point: >98°C
• Appearance: /
• Density: 1.024 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.309mmHg at 25°C
• Refractive Index: n20/D 1.572
• Sensitive: Air Sensitive
• BRN: 1856940
• CAS DataBase Reference: ALLYL PHENYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL PHENYL SULFIDE(5296-64-0)
• EPA Substance Registry System: ALLYL PHENYL SULFIDE(5296-64-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21
• Safety Statements: 23-36/37/39
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 3
• RTECS: WR2400000
• F: 13
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 5296-64-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 625, 1984Tetrahedron, 47, p. 8621, 1991 DOI: 10.1016/S0040-4020(01)82405-4Tetrahedron Letters, 20, p. 1481, 1979

Purification Methods

Dissolve the sulfide in Et2O, wash with alkali, H2O, dry over CaCl2, evaporate and fractionally distil it, preferably under vacuum. It should not give a precipitate with an alcoholic solution of Pb(OAc)2. [Hurd & Greengard J Am Chem Soc 52 3356 1930, Tarbell & McCall J Am Chem Soc 74 48 1952, Beilstein 6 IV 1479.]

InChI:InChI=1/C9H10S/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2

Upstream product

• 108-98-5 thiophenol 
• 106-95-6 allyl bromide 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 138535-23-6 2-propenethiotrimethylstannane 
• 556-56-9 allyl iodid 
• 57340-80-4 thallium thiophenoxide 
• 19093-37-9 allyl phenyl sulfoxide 
• 108-24-7 acetic anhydride 
• 136679-14-6 2-iodo-3-phenylthio-1-propene 
• 64-19-7 acetic acid 
• 54739-05-8 allyloxy-tris(dimethylamino)phosphonium hexafluorophosphate 
• 882-33-7 diphenyldisulfane 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 300-57-2 allylbenzene 
• 108-98-5 thiophenol 
• 22103-05-5 1-(phenylthio)-1-propene 
• 16212-05-8 (allylsulfonyl)benzene 
• 19093-37-9 allyl phenyl sulfoxide 
• 6165-54-4 2-allylbenzenethiol 
• 3959-23-7 benzenesulfonylacetic acid 
• 69668-76-4 1-Chlor-2-methylthio-3-phenylthio-propan 
• 37912-26-8 Dithioacetic acid 1-methyl-2-phenylsulfanyl-ethyl ester 
• 2114-42-3 allylcyclohexane 
• 91789-01-4 (1RS),(2RS)-1-(1-phenylthioprop-2-enyl)indan-2-ol 
• 97370-20-2 1,1-Diphenyl-2-(phenylthio)-3-buten-1-ol 
• 882971-43-9 1-<1-(Phenylthio)-2-propenyl>-2-cyclohexen-1-ol 
• 135277-65-5 1-phenyl-2-(phenylthio)pent-4-en-1-one 

Relevant articles and documents

Size-dependent oxidation of monodisperse silicon nanocrystals with allylphenylsulfide surfaces

The synthesis and characterization of size-separated silicon nanocrystals functionalized with a heteroatom-substituted organic capping group, allylphenylsulfide, via photochemical hydrosilylation are described for the first time. These silicon nanocrystals form colloidally stable and highly photoluminescent dispersions in nonpolar organic solvents with an absolute quantum yield as high as 52% which is 20% above that of the allylbenzene analogue. Solutions of the size-separated fractions are characterized over time to monitor the effect of aging in air by following the change of their photoluminescence and absolute quantum yields, supplemented by transmission electron microscopy.

Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes

A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent

A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.