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363197

Sigma-Aldrich

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:
49762-08-5
Molecular Weight:
147.22
Beilstein:
1210145
MDL number:
MFCD00077793
UNSPSC Code:
12352100
PubChem Substance ID:
24862354
NACRES:
NA.22

Assay

97%

mp

92-94 °C (lit.)

solubility

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

functional group

thioether

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

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Certificates of Analysis (COA)

Lot/Batch Number
19612CA
08911DQ

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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)
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)
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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