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| | (R)-(+)-Methyl p-tolyl sulfoxide Basic information |
| | (R)-(+)-Methyl p-tolyl sulfoxide Chemical Properties |
| 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 |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | F | 3-10 | | HS Code | 2930909899 | | Storage Class | 11 - Combustible Solids |
| | (R)-(+)-Methyl p-tolyl sulfoxide Usage And Synthesis |
| 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).
 | | Synthesis | Highly sensitive to air and moisture. Its generation and handling must be carried out under an inert atmosphere of nitrogen or argon. Normally, preparation is carried out immediately prior to use. |
| | (R)-(+)-Methyl p-tolyl sulfoxide Preparation Products And Raw materials |
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