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69400

Sigma-Aldrich

6-Methyl-2-thiouracil

purum, ≥98.0% S basis (elemental analysis)

Synonym(s):

Basethyrin, Methiocil, Thiothymin, 4-Hydroxy-2-mercapto 6-methylpyrimidine, MZU

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About This Item

Empirical Formula (Hill Notation):
C5H6N2OS
CAS Number:
56-04-2
Molecular Weight:
142.18
Beilstein:
115648
EC Number:
200-252-3
MDL number:
MFCD00006040
UNSPSC Code:
12352100
PubChem Substance ID:
329761639
NACRES:
NA.22
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grade

purum

Quality Level

300

Assay

≥98.0% S basis (elemental analysis)

form

crystals

mp

~330 °C (dec.) (lit.)

SMILES string

CC1=CC(=O)NC(=S)N1

InChI

1S/C5H6N2OS/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)

InChI key

HWGBHCRJGXAGEU-UHFFFAOYSA-N

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General description

6-Methyl-2-thiouracil possesses antithyroid activity.[1]

Application

6-Methyl-2-thiouracil can be used in:
  • Synthesis of luminescent gold(I) thiouracilate complexes as emissive materials.[2]
  • Synthesis of uracil-containing histone deacetylase inhibitors.[3]
  • Synthesis of S-dihydro-alkylthio-benzyl-oxopyrimidines (S-DABOs) based anti-HIV agents.[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV1917
BCBS9703V
BCBS3283V
BCBS3282V
BCBS2229V

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Synthesis and biological properties of novel, uracil-containing histone deacetylase inhibitors.
Mai A, et al.
Journal of Medicinal Chemistry, 49(20), 6046-6056 (2006)
Antithyroid Drugs and their Analogues Protect Against Peroxynitrite-Mediated Protein Tyrosine Nitration-A Mechanistic Study.
Bhabak KP and Mugesh G
Chemistry?A European Journal , 16(4), 1175-1185 (2010)
Synthesis and biological investigation of S-aryl-S-DABO derivatives as HIV-1 inhibitors.
Mugnaini C, et al.
Bioorganic & Medicinal Chemistry Letters, 16(13), 3541-3544 (2006)
P Batjoens et al.
Journal of chromatography. A, 750(1-2), 127-132 (1996-10-25)
A more sensitive method was developed using the hyphenated technique of gas chromatography-mass spectrometry (GC-MS) supplementary to the official high-performance thin-layer chromatography (HPTLC) method. Even combined with less efficient extraction and clean-up methods, GC-MS is able to lower the detection
A M Attia et al.
Nucleosides & nucleotides, 18(10), 2307-2315 (2000-01-05)
N3-beta-D-glucopyranosyl, galactopyranosyl and xylopyranosyl 6-methyl-2-methylthiouracil and their 5-bromo derivatives have been synthesized by coupling an alpha-acetobromosugar with the corresponding thiouracil. The new modified thiouridine analogues were evaluated for their inhibitory activity against Human Immunodeficiency Virus (HIV) replication in MT-4 cells
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