| Identification | Back Directory | [Name]
(R)-(+)-Methyl p-tolyl sulfoxide | [CAS]
1519-39-7 | [Synonyms]
(R)-(+)-METHYL P-TOLYL SULFOXIDE
(R)-methyl4-methylphenylsulfoxide
1-Methanesulfinyl-4-methyl-benzene
(R)-(+)-Methyl p-tolyl sulfoxide 99%
1-methyl-4-[(R)-methylsulfinyl]benzene
(R)-1-Methyl-4-(Methylsulfinyl)benzene
Benzene, 1-methyl-4-[(R)-methylsulfinyl]- | [Molecular Formula]
C8H10OS | [MDL Number]
MFCD00151502 | [MOL File]
1519-39-7.mol | [Molecular Weight]
154.23 |
| Chemical Properties | Back Directory | [Melting point ]
73-75 °C(lit.) | [alpha ]
145 º (c=2, acetone) | [Boiling point ]
247.62°C (rough estimate) | [density ]
1.1125 (rough estimate) | [refractive index ]
1.5780 (estimate) | [storage temp. ]
Storage temp. 2-8°C | [form ]
Solid | [Appearance]
White to off-white Solid | [Optical Rotation]
[α]20/D +145°, c = 2 in acetone | [BRN ]
2040677 | [InChI]
1S/C8H10OS/c1-7-3-5-8(6-4-7)10(2)9/h3-6H,1-2H3/t10-/m1/s1 | [InChIKey]
FEVALTJSQBFLEU-SNVBAGLBSA-N | [SMILES]
Cc1ccc(cc1)S(C)=O |
| Hazard Information | Back Directory | [Uses]
Used in asymmetric synthesis; adds diastereoselectively to carbony compounds, esters, imines, nitrones, and nitrile oxides. | [General Description]
(R)-(+)-Methyl p-tolyl sulfoxide may be used to prepare (R)-(+)-methyl 3,5-dimethoxy-6-[8-oxo-9-(p-tolylsulfinyl) nonyl] benzoate, an intermediate for (R)-lasiodiplodin synthesis. Its anions undergo addition reaction with nitrones to form optically active a-substituted N-hydroxylamines. (R)-(+)-Methyl p-tolyl sulfoxide also reacts with O-mesitylsulfonylhydroxylamine (MSH) to form (-)-(R)-S-methyl-S-p-tolylsulfoximine. | [Synthesis]
(R)-(+)-Methyl p-tolyl sulfoxide is prepared by the nucleophilic displacement of (-)- (1R,2S,5R)-Menthyl (S)-p-Toluenesulfinate with methyl Grignard with complete inversion of configuration at sulfur (eq 1).
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