| Identification | Back Directory | [Name]
ALLYL PHENYL SULFOXIDE | [CAS]
19093-37-9 | [Synonyms]
Einecs 242-811-4
Phenyl allyl sulfoxide
ALLYL PHENYL SULFOXIDE
(Allylsulfinyl)benzene
(allylsulphinyl)benzene
(2-Propenylsulfinyl)benzene
Phenyl (2-propenyl) sulfoxide
ALLYL PHENYL SULFOXIDE, TECH.
Benzene, (2-propen-1-ylsulfinyl)- | [EINECS(EC#)]
242-811-4 | [Molecular Formula]
C9H10OS | [MDL Number]
MFCD00040897 | [MOL File]
19093-37-9.mol | [Molecular Weight]
166.24 |
| Chemical Properties | Back Directory | [Boiling point ]
85 °C0.3 mm Hg(lit.) | [density ]
1.122 g/mL at 20 °C(lit.) | [refractive index ]
n20/D 1.578 | [solubility ]
sparingly soluble hexane; sol most other organic solvents |
| Hazard Information | Back Directory | [Chemical Properties]
Allyl Phenyl Sulfoxide can undergo allylic rearrangement, bp 103-104 °C/0.36 mmHg; d 1.1205 g cm-3. | [Uses]
Allyl Phenyl Sulfoxide is use in: allylic sulfoxides undergo allylic rearrangement to form sulfenate esters, allowing the generation of allylic alcohols; metalated derivatives serve as ambident nucleophiles; precursors to Pummerer intermediates.
| [Synthesis Reference(s)]
Synthesis, p. 815, 1983 DOI: 10.1055/s-1983-30526
Tetrahedron Letters, 35, p. 1413, 1994 DOI: 10.1016/S0040-4039(00)76232-0 | [Synthesis]
Oxidation of Allyl Phenyl Sulfide in dichloromethane with m-Chloroperbenzoic Acid acid (1.2 equiv) added slowly as a solution in dichloromethane at -70 °C affords the sulfoxide in high yields with minimal over-oxidation to the sulfone. The m-chlorobenzoic acid formed may be removed simply by filtration. Other oxidizing agents such as Sodium Bromite3 and Trifluoroperacetic Acid4 afford the sulfoxide in yields greater than 80% and are also highly selective.
| [Solubility in organics]
Allyl Phenyl Sulfoxide is sparingly soluble hexane; sol most other organic solvents.
| [storage]
No special precautions are required. The sulfoxide may be handled normally at the bench for general weighing and transferring. However, for maximum shelf-life it is recommended that it be stored at 4 °C in a sealed vessel with exclusion of oxygen and moisture.
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SIGMA-RBI
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