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561487

Sigma-Aldrich

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

97%

Synonym(s):

1,2-Benzisothiazolone, 1,2-Benzoisothiazol-3-one, 1,2-benzothiazoline-3-one, 2,3-Dihydro-1,2-benzothiazol-3-one, 3-Hydroxy-1,2-benzisothiazole, Benzisothiazolin-3-one

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About This Item

Empirical Formula (Hill Notation):
C7H5NOS
CAS Number:
2634-33-5
Molecular Weight:
151.19
EC Number:
220-120-9
MDL number:
MFCD00127753
UNSPSC Code:
12352100
PubChem Substance ID:
24879952
NACRES:
NA.22

assay

97%

form

solid

mp

154-158 °C (lit.)

SMILES string

Oc1nsc2ccccc12

InChI

1S/C7H5NOS/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9)

InChI key

DMSMPAJRVJJAGA-UHFFFAOYSA-N

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General description

1,2-Benzisothiazol-3(2H)-one can be synthesized by reacting 2-mercaptobenzoic acid with diphenyl phosphoryl azide.

Disclaimer

The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Convenient Synthesis of 1, 2-Benzisothiazol-3 (2H)-ones by Cyclization Reaction
of Acyl Azide
Chiyoda T, et al.
Synlett, 2000(10), 1427-1428 (2000)
Alan Rolfe et al.
Journal of combinatorial chemistry, 11(4), 732-738 (2009-06-10)
A sequential three-component synthesis of functionalized benzisothiazoline-3-acetic acid 1,1-dioxides utilizing a domino Heck-aza-Michael pathway is reported. This one-pot procedure rapidly assembles functionalized benzylsulfonamides, which undergo a palladium-catalyzed, domino, Heck-aza-Michael transformation in an experimentally straightforward manner. This attractive protocol has been
Kristiina Aalto-Korte et al.
Contact dermatitis, 57(6), 365-370 (2007-11-09)
Benzisothiazolinone is used as a slimicide in the manufacture of disposable powder-free polyvinyl chloride (PVC) gloves. We recently reported 6 patients from dentistry and health care probably sensitized to benzisothiazolinone in PVC gloves. The study aimed to investigate how widely
William L Jorgensen et al.
Bioorganic & medicinal chemistry letters, 21(15), 4545-4549 (2011-07-02)
Substituted N-phenylbenzisothiazolones have been investigated as inhibitors of the tautomerase activity of the proinflammatory cytokine MIF (macrophage migration inhibitory factor). Numerous compounds were found to possess antagonist activity in the low micromolar range with the most potent being the 6-hydroxy
Deepu Alex et al.
Antimicrobial agents and chemotherapy, 56(9), 4630-4639 (2012-06-13)
We have identified four synthetic compounds (DFD-VI-15, BD-I-186, DFD-V-49, and DFD-V-66) from an amino acid-derived 1,2-benzisothiazolinone (BZT) scaffold that have reasonable MIC(50) values against a panel of fungal pathogens. These compounds have no structural similarity to existing antifungal drugs. Three
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