ALLYL PHENYL SULFOXIDE Chemical Properties

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21

Safety Statements 

23-36/37

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

ALLYL PHENYL SULFOXIDE Usage And Synthesis

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.

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.

ALLYL PHENYL SULFOXIDE(19093-37-9)Related Product Information

• Allyl phenyl sulfone
• Phenyl sulfoxide
• DIOXO(PHENYL)(3-PHENYL-2-PROPENYL)-LAMBDA6-SULFANE
• BIS(P-DIMETHYLAMINOSTYRYL)-P-METHYLPHENYLSULFONYLMETHANE
• ALLYL PHENYL SULFOXIDE
• 5,5-DIMETHYL-3-OXO-2-[(PHENYLSULFONYL)METHYL]-1-CYCLOHEXENYL 4-METHYLBENZENECARBOXYLATE
• 5-PHENYL-3-(PHENYLSULFANYL)-2-[(PHENYLSULFONYL)METHYL]-2-CYCLOHEXEN-1-ONE
• 4-BROMO-3-(((4-CHLOROPHENYL)SULFONYL)METHYL)-2-METHYL-1-PHENYL-3-PYRAZOLIN-5-ONE
• 3-HYDROXY-5,5-DIMETHYL-2-[(PHENYLSULFONYL)METHYL]-2-CYCLOHEXEN-1-ONE
• N,N-DIMETHYL-4-PHENYL-2-(PHENYLSULFONYL)-1,3-BUTADIEN-1-AMINE
• 3-CHLORO-6-([3-(TRIFLUOROMETHYL)PHENYL]SULFINYL)[1,2,4]TRIAZOLO[4,3-B]PYRIDAZINE
• 4-PHENYL-2-(PHENYLSULFONYL)-3-BUTENAL O-METHYLOXIME
• 2-[(4-CHLOROPHENYL)SULFONYL]-4-PHENYL-3-BUTENAL OXIME
• 2-[(4-CHLOROPHENYL)SULFONYL]-4-PHENYL-3-BUTENAL O-(2,4-DICHLOROBENZYL)OXIME
• (4-CHLOROPHENYL)(DIOXO)(3-PHENYL-2-PROPENYL)-LAMBDA6-SULFANE
• 4-BROMO-2-METHYL-3-(((4-METHYLPHENYL)SULFONYL)METHYL)-1-PHENYL-3-PYRAZOLIN-5-ONE
• 4-PHENYL-2-(PHENYLSULFONYL)-3-BUTENAL OXIME
• 5-(4-CHLOROPHENYL)-2-[(PHENYLSULFONYL)METHYL]-3-(2-PYRIDINYLSULFANYL)-2-CYCLOHEXEN-1-ONE