3-Chloro-1,2-benzisothiazole Chemical Properties

Melting point:

38-39°C

Boiling point:

80-86°C 0,75mm

Density 

1.435±0.06 g/cm3(Predicted)

Flash point:

80-86°C/0.75mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform, Dichloromethane and Ethyl Acetate.

form 

Solid

pka

1.05±0.50(Predicted)

color 

White

BRN 

119370

InChI

InChI=1S/C7H4ClNS/c8-7-5-3-1-2-4-6(5)10-9-7/h1-4H

InChIKey

BCPVKLRBQLRWDQ-UHFFFAOYSA-N

SMILES

S1C2=C(C=CC=C2)C(Cl)=N1

CAS DataBase Reference

7716-66-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:ALFA

3-Chloro-1,2-benzisothiazole Usage And Synthesis

Chemical Properties

White Solid

Uses

3-Chloro-1,2-benzisothiazole is used as an intermediate of Ziprasidone.

Synthesis

Example 1A: To a 1 L four-necked round-bottomed flask equipped with a mechanical stirrer, a thermometer and a reflux condenser tube were sequentially added 75.6 g (0.5 mol) of 1,2-benzisothiazol-3-one, 54.8 g (0.75 mol) of N,N-dimethylformamide (DMF) and 100.0 g of chlorobenzene as a solvent. Stirring was turned on and the temperature of the reaction system was maintained between 70 °C and 80 °C, followed by the slow dropwise addition of 71.4 g (0.6 mol) of thionyl chloride (SOCl2) over a period of 1 hour. After the dropwise addition was completed, the reaction mixture was kept at the same temperature and the reaction was continued with stirring for 8 hours. Upon completion of the reaction, the liquid reaction mixture was concentrated under reduced pressure to remove the solvent and unreacted thionyl chloride. The resulting crude product was subjected to decompression distillation at 128 °C under reduced pressure at 0.93 kPa to yield 75.1 g (0.45 mol) of the target product 3-chloro-1,2-benzisothiazole in 90% yield as 1,2-benzisothiazol-3-one.

References

[1] Patent: US5883258, 1999, A
[2] Patent: US2013/5983, 2013, A1. Location in patent: Page/Page column 2-3
[3] Patent: US5883258, 1999, A
[4] Tetrahedron Letters, 2011, vol. 52, # 50, p. 6775 - 6778
[5] Journal of Medicinal Chemistry, 1986, vol. 29, # 3, p. 359 - 369

3-Chloro-1,2-benzisothiazole(7716-66-7)Related Product Information

• 2-Mercaptobenzothiazole
• Methylchloroisothiazolinone/methylisothiazolinone mixture (MCIT/MIT)
• 2-Methyl-4-isothiazolin-3-one
• Benzothiazole
• Probenazole
• 1,2-Benzisothiazol-3(2H)-one
• Isothiazole
• 2,2'-Dithiobis(benzothiazole)
• Difluorochloromethane
• FER1443,Landromil,Ticlaton,Ticlatone,3-Hydroxy-6-chloro-1,2-benzisothiazole
• 3-Chloro-benzo[d]isothiazole 1,1-dioxide
• 6-CHLORO-1,2-BENZISOTHIAZOLE-3-CARBOXYLIC ACID
• 3-Chloro-1,2-benzisothiazole
• 3-TERT-BUTYL-4-CHLORO-1,2-BENZISOTHIAZOLE-7-CARBALDEHYDE 1,1-DIOXIDE
• 3-(1H-Tetrazol-5-yl)methyl-5-chloro-1,2-benzisothiazole
• 4-chloro-1,2-benzisothiazole
• 5-Chloro-1,2-benzisothiazole-3-acetic acid
• methyl 3-chloro-1,2-benzisothiazole-6-carboxylate 1,1-dioxide