363197
3-Hydroxy-4-methyl-2(3H)-thiazolethione
97%
Synonym(s):
2-Mercapto-4-methylthiazole 3-oxide
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About This Item
Empirical Formula (Hill Notation):
C4H5NOS2
CAS Number:
Molecular Weight:
147.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1210145
Assay:
97%
InChI
1S/C4H5NOS2/c1-3-2-8-4(7)5(3)6/h2,6H,1H3
SMILES string
CC1=CSC(=S)N1O
InChI key
LOKDIDVKVVVVHK-UHFFFAOYSA-N
assay
97%
Quality Level
solubility
methanol: soluble 25 mg/mL, clear, brownish-yellow to brown
functional group
thioether
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Solid-state study of cyclic thiohydroxamic acids: 1-hydroxy-2 (1H)-pyridinethione and 3-hydroxy-4-methyl-2 (3H)-thiazolethione.
Bond AD and Jones W.
Journal of Physical Organic Chemistry, 13(7), 395-404 (2000)
Synthesis and X-ray crystal structures of bis (3-hydroxy-4-methyl-2 (3H)-thiazolethiolato-S 2, O) bis (dimethylsulfoxide-O) M, M= cobalt (II) and nickel (II).
Bond AD and Jones W.
Transition Met. Chem. (London), 27(4), 407-410 (2002)
Divalent complexes of 3-hydroxy-4-methyl-2 (3H)-thiazolethione with Co-Zn: synthesis, X-ray crystal structures and the structure-directing influence of C-HS interactions.
Bond AD and Jones W.
J. Chem. Soc., Dalton Trans., 20, 3045-3051 (2001)
Journal of the Chemical Society. Perkin Transactions 1, 39-39 (1986)
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