(R)-(+)-Methyl p-tolyl sulfoxide

(R)-(+)-Methyl p-tolyl sulfoxide Property

Melting point:

73-75 °C(lit.)

Boiling point:

247.62°C (rough estimate)

alpha 

145 º (c=2, acetone)

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 activity

[α]20/D +145°, c = 2 in acetone

BRN 

2040677

Safety

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-10

HS Code 

2930909899

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

(R)-(+)-Methyl p-tolyl sulfoxide Chemical Properties,Usage,Production

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.