(R)-tert-Butanethiosulfinate

(R)-tert-Butanethiosulfinate Property

Melting point:

78.5-81.2 °C

Boiling point:

72 °C(Press: 0.30 Torr)

Density 

1.055±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

CAS DataBase Reference

67734-35-4(CAS DataBase Reference)

Safety

HS Code 

2930909899

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

(R)-tert-Butanethiosulfinate Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of (R)-tert-butyl sulfinic acid thio-tert-butyl ester from tert-butyl disulfide was as follows: first, ligand L1 was prepared by reacting an equal amount of (1S,2R)-serpentinic acid trimethylsilyl ether with 3,5-dimethylsalicylaldehyde (for details of the preparation, see: Org. Synth. 2005, 82, 157). Subsequently, ligand L1 (5.0 mmol) was dissolved with VO(acac)2 (1.27 g, 4.8 mmol) in acetone and the reaction was stirred for 1 hour. After the color of the system darkened, the progress of the reaction was monitored by TLC. Next, tert-butyl disulfide (171.2 g, 0.96 mol) was dissolved in 190 mL of acetone and the reaction temperature was controlled at -5°C to 0°C. At this temperature, 25% hydrogen peroxide (1.0 mol) was added slowly dropwise, and the dropwise process took about 20-22 hours. After completion of the reaction, the reaction temperature was maintained until the ratio of feedstock to product reached 90:1, which was taken as the end point of the reaction. Throughout the process, the reaction temperature should not exceed 35°C. At the end of the reaction, the solvent was removed by distillation under reduced pressure. To the residue was added 350 mL of 2-methyltetrahydrofuran, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solution was tested by filtration. The yield of (R)-tert-butylsulfinyl tert-butyl thioester was 93% (173.5 g, 0.89 mol) with an ee value of 96.2%.

References

[1] Patent: CN106478471, 2017, A. Location in patent: Paragraph 0016; 0017; 0020; 0021
[2] Journal of the American Chemical Society, 1998, vol. 120, # 32, p. 8011 - 8019
[3] Journal of the American Chemical Society, 1998, vol. 120, # 32, p. 8011 - 8019
[4] Patent: WO2017/51326, 2017, A1. Location in patent: Page/Page column 44