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363197

Sigma-Aldrich

3-Hydroxy-4-methyl-2(3H)-thiazolethione

97%

Synonym(s):
2-Mercapto-4-methylthiazole 3-oxide
Empirical Formula (Hill Notation):
C4H5NOS2
CAS Number:
Molecular Weight:
147.22
Beilstein:
1210145
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

92-94 °C (lit.)

solubility

methanol: soluble 25 mg/mL, clear, brownish-yellow to brown

SMILES string

CC1=CSC(=S)N1O

InChI

1S/C4H5NOS2/c1-3-2-8-4(7)5(3)6/h2,6H,1H3

InChI key

LOKDIDVKVVVVHK-UHFFFAOYSA-N

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General description

3-Hydroxy-4-methyl-2(3H)-thiazolethione (HMTT) is a cyclic thiohydroxamic acid. It forms divalent complexes with the first-row d-block elements Co-Zn. Hydrated form of HMTT exhibits enhanced thermal stability and solubility compared with the anhydrous form. HMTT possess a chelating unit similar to pyrithione. Solid state chemistry of HMTT and its complexes with d-block elements has been reported.

Application

3-Hydroxy-4-methyl-2(3H)-thiazolethione may be employed as fungicide and alkoxy-radical precursors in the synthetic procedures. It may be useful in the Barton reaction for the generation of carbon radicals through decarboxylative rearrangement of the corresponding esters.

Packaging

1 g in glass bottle

Certificate of Analysis

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Certificate of Origin

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