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Tioxolone

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Tioxolone Basic information

Product Name:
Tioxolone
Synonyms:
  • thioxolon
  • Thiphen
  • tioxolon
  • Trocinate
  • 6-HYDROXY-1,3-BENZOXANTHIOL-2-ONE
  • 6-HYDROXY-1,3-BENZOXATHIOL-2-ONE
  • 6-HYDROXY-1,3-BENZOXATHIOL-2-ONE, 98+%
  • 6-Hydroxy-2-oxo-1,3-benzoxathiole
CAS:
4991-65-5
MF:
C7H4O3S
MW:
168.17
EINECS:
225-653-0
Product Categories:
  • Heterocyclic Compounds
  • STEPIN
Mol File:
4991-65-5.mol
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Tioxolone Chemical Properties

Melting point:
158-160 °C(lit.)
Boiling point:
267.1°C (rough estimate)
Density 
1.4844 (rough estimate)
refractive index 
1.5151 (estimate)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
95% ethanol: soluble50mg/mL, clear to very slightly hazy, colorless to yellow
form 
A solid
pka
8.14±0.20(Predicted)
color 
Light yellow to yellow
Merck 
9456
LogP
1.770 (est)
CAS DataBase Reference
4991-65-5(CAS DataBase Reference)
NIST Chemistry Reference
Tioxolone(4991-65-5)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26
WGK Germany 
3
RTECS 
DM2953750
HS Code 
2934999090

MSDS

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Tioxolone Usage And Synthesis

Chemical Properties

light yellow to beige powder

Originator

Acnosan,Unia

Uses

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

Uses

antiseborrhoic

Definition

ChEBI: A 1,3-benzoxathiole having a hydroxy substituent at the 6-position.

Manufacturing Process

40 g potassium thiocyanate in 50 ml of water are added, while stirring at room temperature, to a solution of 11 g of resorcinol and 50 g of crystallized copper sulfate in 250 ml of water. The black cupric thiocyanate formed becomes colorless after a short time, which indicates that the introduction of thiocyanogen is terminated. The cuprous thiocyanate is removed by filtering with suction and then washed with water; the filtrate is mixed with 50 ml of a 2 N sodium carbonate solution, whereby the imino-thiocarbonate of resorcinol separates in the form of a colorless crystalline body. The yield amounts to 16 g. The new compound which melts at 149°C dissolves very easily in many organic solvents and in mineral acids.
A 10% solution of the imino-thiocarbonate of resorcinol in 10% hydrochloric acid is heated for 15 min on the steam bath. The 6-hydroxy-1,3-benzoxathiol- 2-one (thiocarbonate free from) nitrogen separates, on cooling, in the form of fine crystals melting at 158°C.

Therapeutic Function

Antiseborreic, Antifungal, Keratolytic

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.

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