(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE Chemical Properties

Melting point:

99-104 °C

Boiling point:

402.3±38.0 °C(Predicted)

Density 

1.08

refractive index 

-199 ° (C=1.5, Acetone)

storage temp. 

-20°C

solubility 

Acetone (Slightly), Chloroform (Slightly)

form 

Solution

color 

Yellow to brown or gray

optical activity

[α]20/D 195°, c = 2 in acetone

BRN 

3207468

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

(1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate is a reactant used in the synthesis of sulfoxide pincer complexes of Mg, Rh and Ir.

Uses

(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate can react with:

• metal ketimines to form enantiopure sulfinimines
• p-(methylthio)benzaldehyde to form (S)-(-)-N-(4-methylthiobenzylidene)-p-toluenesulfinimine

General Description

(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate is mainly used for the introduction of p-toluenesulfinyl group in asymmetric synthesis.

Synthesis

The general procedure for the synthesis of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinyl ester from p-toluenesulfinic acid and L-menthol was as follows: to a 250 mL flame-dried and N2 purged round-bottomed flask were added sequentially p-toluenesulfinic acid (0.525 g, 3.36 mmol), 4-bromobenzyl alcohol (0.598 g, 3.20 mmol) and DMAP (0.078 g, 0.64 mmol), which were then dissolved in anhydrous CH2Cl2 (14 mL). To this solution was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.644 g, 3.36 mmol) in a single addition and the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was diluted with CH2Cl2 (30 mL) and washed sequentially with 1M HCl (30 mL) and brine (30 mL). The organic layer was separated, dried with MgSO4, filtered and the solvent was removed under reduced pressure. Finally, the crude product was purified by fast column chromatography.

References

[1] Synthesis (Germany), 2018, vol. 50, # 24, p. 4855 - 4866
[2] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1646 - 1652
[3] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1646 - 1652
[4] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 356, p. 371 - 387
[5] Tetrahedron, 1999, vol. 55, # 8, p. 2311 - 2316

(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE(1517-82-4)Related Product Information

• p-Toluenesulfonic acid
• P-TOLUENESULFINIC ACID
• (1S,2R,5S)-MENTHYL (R)-P-TOLUENESULFINATE,(1S,2R,5S)-(+)-MENTHYL (R)-P-TOLUENESULFINATE,(+)-(1S)-Menthyl (R)-p-toluenesulfinate
• DL-Menthol
• 2,5-DIMETHYLCYCLOHEXANOL
• 3,7-DIMETHYL-1-OCTANOL
• METHYL P-TOLUENESULFINATE
• (1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE
• 2-Methylcyclohexanol
• (+)-MENTHOL
• DL-Menthol
• 2-ETHYLCYCLOHEXANOL