1,2-Benzisothiazol-3(2H)-one

Base Information

• Chemical Name: 1,2-Benzisothiazol-3(2H)-one
• CAS No.: 2634-33-5
• Deprecated CAS: 101964-01-6,40991-37-5,54392-14-2,75037-67-1,552320-00-0,1094749-54-8,919284-21-2,1148150-72-4,1376937-61-9,1399460-92-4,934197-15-6,1813531-93-9,1623463-70-6,2376801-76-0,1094749-54-8,40991-37-5,54392-14-2,552320-00-0,75037-67-1,919284-21-2
• Molecular Formula: C7H5NOS
• Molecular Weight: 151.189
• Hs Code.: 29339900
• European Community (EC) Number: 220-120-9
• UNII: HRA0F1A4R3
• DSSTox Substance ID: DTXSID5032523
• Nikkaji Number: J7.640F
• Wikipedia: Benzisothiazolinone
• Wikidata: Q411746
• RXCUI: 1368198
• Metabolomics Workbench ID: 46529
• ChEMBL ID: CHEMBL297304
• Mol file: 2634-33-5.mol

Synonyms:1,2-benzisothiazolin-3-one;1,2-benzisothiazoline-3-one;benzisothiazolinone;benzisothiazolone;Proxel

Chemical Property of 1,2-Benzisothiazol-3(2H)-one

Chemical Property:

• Appearance/Colour: white to pale yellow powder
• Vapor Pressure: 0.183mmHg at 25°C
• Melting Point: 154-158 ºC
• Refractive Index: 1.66
• Boiling Point: 204.5 ºC at 760 mmHg
• PKA: 10.19±0.20(Predicted)
• Flash Point: 77.5 ºC
• PSA: 61.10000
• Density: 1.367 g/cm³
• LogP: 1.58960
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in dichloromethane, dimethyl sulfoxide, methanol.
• Water Solubility.: 1.288g/L at 20℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 151.00918496
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

Benzoisothiazol-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-38-41-43-50
• Safety Statements: 24-26-37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)NS2
• Description: BIT is an irritant and also a skin sensitizer. Occupational allergie contact dermatitis has been reported mainly related to the use of cutting oils and greases in paint manufacturers, pottery mouldmakers, acrylic emulsion manufacturers, plumbers, printers and lithoprinters, paper makers, an analyticallaboratory, a rubber factory, and in employees manufacturing air fresheners.
• Uses: Antimicrobial agent. Isothiazolinone BIT is widely used in industry as a preservative in water-based solutions, such as pastes, paints and cutting oils. It exists at different concentrations in the different Proxel AB, GXL, CRL, XL2, XL, HL, TN, and in Mergal K-10. preservative in cooling fluids, paints, adhesives paper and in the textile industry

Technology Process of 1,2-Benzisothiazol-3(2H)-one

There total 58 articles about 1,2-Benzisothiazol-3(2H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-cyanothioanisole (6609-54-7) → 1,2-benzisothiazolin-3-one (2634-33-5)

Guidance literature:

2-cyanothioanisole; With chlorine; In water; chlorobenzene; at 45 - 70 ℃; for 5h;

With water; sodium hydroxide; In chlorobenzene; at 65 - 70 ℃; Concentration; Time;

Reference yield: 97.0%

2-Chlorobenzonitrile (873-32-5) → 1,2-benzisothiazolin-3-one (2634-33-5)

Guidance literature:

2-Chlorobenzonitrile; With tetrabutylammomium bromide; sodium thioethylate; In water; chlorobenzene; for 2h; Inert atmosphere; Reflux;

With sulfuryl dichloride; water; In chlorobenzene; at 5 - 80 ℃; for 1h;

Reference yield: 85.0%

2-methylsulfanyl-benzamide (54705-16-7) → 1,2-benzisothiazolin-3-one (2634-33-5)

Guidance literature:

With N-bromophthalimide; In 1,1,2,2-tetrachloroethane; at 50 - 60 ℃;

upstream raw materials:

2,2'-dithiodibenzoic acid dichloride

3H-1,2-benzodithiol-3-one

2,2'-dithiobisbenzamide

3-ethoxy-1,2-benzisothiazole

Downstream raw materials:

3-[5-(4-nitro-phenoxy)-pentyloxy]-benz[d]isothiazole

benzonitrile

3-chloro-1,2-benzisothiazole

2-mercaptobenzamide

Refernces

• 1、 Jin, Chun Keun,Moon, Jung-Kyen,Lee, Woo Song,Nam, Keun Soo. "Process Development of 1,2-Benzisothiazolin-3(2H)-one by Replacing of the Toxic Materials". . p. 1967 - 1968. Retrieved 2003.
• 2、 -. "Dimer impurity in ziprasidone hydrochloride raw material and preparation method thereof". Paragraph 0133-0136. . Retrieved 2021/06/09.
• 3、 Jin, Wen Bin,Xu, Chen,Cheung, Qipeng,Gao, Wei,Zeng, Ping,Liu, Jun,Chan, Edward W.C.,Leung, Yun-Chung,Chan, Tak Hang,Wong, Kwok-Yin,Chen, Sheng,Chan, Kin-Fai. "Bioisosteric investigation of ebselen: Synthesis and in vitro characterization of 1,2-benzisothiazol-3(2H)-one derivatives as potent New Delhi metallo-β-lactamase inhibitors". . . Retrieved 2020/04/30.