ISOTHIAZOLINE 1,1-DIOXIDE Chemical Properties

Melting point:

145-146 °C

Boiling point:

128-132 °C(Press: 0.18 Torr)

Density 

1.326±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

11.52±0.20(Predicted)

form 

liquid

color 

Colorless to light yellow

InChI

InChI=1S/C3H7NO2S/c5-7(6)3-1-2-4-7/h4H,1-3H2

InChIKey

XGYCWCIGCYGQFU-UHFFFAOYSA-N

SMILES

S1(=O)(=O)CCCN1

Safety Information

WGK Germany 

3

HS Code 

2934999090

ISOTHIAZOLINE 1,1-DIOXIDE Usage And Synthesis

Uses

Propane Sultam is a reactant used in the synthesis of orally bioavailable hebatits B caspid inhibitors as well as in the preparation of cryptochrome imhibitors as antidiabetic agents.

Synthesis

At room temperature, 3-chloropropane-1-sulfonamide (27 g, 170 mmol, 1 eq.) was dissolved in ethanol (250 ml), followed by addition of sodium ethoxide (11.7 g, 170 mmol, 1 eq.). The reaction mixture was heated to reflux for 5 h. After completion of the reaction it was cooled to room temperature and concentrated under reduced pressure. The residual solid was fully extracted with dichloromethane, the organic phases were combined and concentrated under reduced pressure to give 1,1-dioxoisothiazolidine (20 g, 100% yield).

References

[1] Patent: WO2004/50619, 2004, A1. Location in patent: Page 24
[2] Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641
[3] Journal of Organic Chemistry, 1987, vol. 52, # 11, p. 2162 - 2166
[4] Patent: WO2012/3283, 2012, A1. Location in patent: Page/Page column 206-207
[5] Patent: US2012/316147, 2012, A1. Location in patent: Page/Page column 62-63

ISOTHIAZOLINE 1,1-DIOXIDE(5908-62-3)Related Product Information

• Isothiazole-5-methanol
• 3-Aminoisothiazolo[4,3-b]pyridine
• Isothiazole
• Isothiazole-4-carbaldehyde
• (2R)-Bornane-10,2-sultam
• (1R)-(-)-(10-Camphorsulfonyl)oxaziridine
• (+)-(8,8-DICHLOROCAMPHORYLSULFONYL)OXAZIRIDINE
• (2S)-Bornane-10,2-sultam
• (1S)-(+)-(Camphorylsulfonyl)oxaziridine
• N-(2-CARBOXYBENZOYL)-(-)-10,2-CAMPHORSULTAM
• N-(2-CARBOXY-4,5-DICHLOROBENZOYL)-(-)-10,2-CAMPHORSULTAM
• N-(2-CARBOXY-4,5-DICHLOROBENZOYL)-(+)-10,2-CAMPHORSULTAM
• (2R)-BORNANE-10,2-SULTAM GLYCINATE
• N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM
• N-ACETYL-(2S)-BORNANE 10,2-SULTAM
• (S)-(+)-(2-BUTENOYL)-2 10-CAMPHORSULTAM
• (2S)-BORNANE-10,2-SULTAM GLYCINATE
• N-PROPIONYL-(2S)-BORNANE- 10,2-SULTAM