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Key Documents

217077

Sigma-Aldrich

6-Hydroxy-1,3-benzoxathiol-2-one

≥98%

Synonym(s):

Tioxolone

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About This Item

Empirical Formula (Hill Notation):
C7H4O3S
CAS Number:
Molecular Weight:
168.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98%

mp

158-160 °C (lit.)

solubility

95% ethanol: soluble 50 mg/mL, clear to very slightly hazy, colorless to yellow
benzene: soluble
diethyl ether: soluble
isopropanol: soluble
propylene glycol: soluble
toluene: soluble
water: insoluble

SMILES string

Oc1ccc2SC(=O)Oc2c1

InChI

1S/C7H4O3S/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3,8H

InChI key

SLYPOVJCSQHITR-UHFFFAOYSA-N

General description

Antimicrobial and cytostatic properties of 6-hydroxy-1,3-benzoxathiol-2-one has been investigated. Supramolecular structure of 6-hydroxy-1,3-benzoxathiol-2-one has been studied.

Application

6-Hydroxy-1,3-benzoxathiol-2-one was used in the synthesis of heterocycle-phosphor esters having potential antimicrobial activity.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[Antimicrobial and cytostatic properties of 6-hydroxy-1,3-benzoxathiol-2-one (01 1)].
H Goeth et al.
Arzneimittel-Forschung, 19(8), 1298-1304 (1969-08-01)
Contact dermatitis to thioxolone.
J G Camarasa
Contact dermatitis, 7(4), 213-214 (1981-07-01)
Contact dermatitis to thioxolone.
H Näher et al.
Contact dermatitis, 17(4), 250-251 (1987-10-01)
Alessio Innocenti et al.
Bioorganic & medicinal chemistry letters, 18(14), 3938-3941 (2008-06-24)
Inhibition of 13 mammalian isoforms of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), CA I-XV, with thioxolone (6-hydroxy-1,3-benzoxathiol-2-one) and two sulfonamides was investigated. Thioxolone was inefficient for generating isozyme-selective inhibitors, since except for CA I which is inhibited in the
J M Varga et al.
Molecular immunology, 28(6), 641-654 (1991-06-01)
A recently developed solid-phase binding assay was used to investigate the specificity of ligand binding to a mouse monoclonal anti-dinitrophenyl IgE [IgE(aDNP)]. All DNP-amino acids, that were tested, inhibited the binding of radio-labeled IgE(aDNP) to DNP covalently attached to polystyrene

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