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/REAXYS Number:
1210145
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

3

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)
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)
Journal of the Chemical Society. Perkin Transactions 1, 39-39 (1986)

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