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CAS 1450-85-7

2-Mercaptopyrimidine TCI M0937

2-Mercaptopyrimidine TCI M0937

Chemical Identity

CAS No.
1450-85-7
PubChem
CID 1550489·SID 87572919
Formula
C4H4N2S
Molecular weight
112.16 g/mol
Purity
>98.0%(HPLC)
Reference databases
ChEBI·ChemSpider·ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
1H-pyrimidine-2-thione
SMILES
C1=CNC(=S)N=C1
InChIKey
HBCQSNAFLVXVAY-UHFFFAOYSA-N
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TCI M0937 2-Mercaptopyrimidine, CAS 1450-85-7, is an aromatic heterocyclic compound consisting of a pyrimidine ring that carries a mercapto group at the two position. The compound exists in a tautomeric equilibrium between its thiol and thione forms, which gives it dual reactivity through both the sulfur atom and the ring nitrogen atoms. In the laboratory it serves as a heterocyclic building block for the synthesis of sulfur-substituted pyrimidine derivatives, and at the same time as a ligand capable of binding a variety of metal ions and noble metal surfaces.

The most prominent characteristic of this material is the high nucleophilicity of its sulfur atom, which allows the compound to undergo S-alkylation readily with alkyl and benzyl halides to produce pyrimidine thioethers, a motif frequently encountered in bioactive molecules. The combination of sulfur and nitrogen donors lets it act as a chelating ligand that forms stable complexes with transition metals, including silver, gold, copper, and nickel. It is supplied as a solid that is easy to weigh out, and it dissolves in polar solvents such as ethanol and dimethyl sulfoxide as well as in dilute basic solutions, which simplifies the preparation of working solutions at the bench.

In Indonesia, this compound is used chiefly in synthetic organic chemistry and coordination chemistry work at university research laboratories, government research institutes, and industrial development units. Its dual role as both a synthetic intermediate and a metal-binding ligand makes it a practical item to keep on hand for groups that move between heterocyclic synthesis, complex preparation, and surface modification studies within the same programme.

  • Synthesis of substituted pyrimidine derivatives: the mercapto group at position two provides a reactive handle for building sulfur-functionalised pyrimidine scaffolds relevant to medicinal chemistry programmes.
  • S-alkylation to pyrimidine thioethers: the highly nucleophilic sulfur atom reacts readily with alkyl and benzyl halides, giving a thioether motif that appears often in bioactive molecules.
  • Preparation of transition metal complexes: the paired sulfur and nitrogen donors allow the compound to chelate metal centres and form stable coordination complexes for structural and reactivity studies.
  • Ligand for silver, gold, copper, and nickel chemistry: the compound binds these metal ions in a defined manner, supporting the preparation of well-characterised complexes of each metal.
  • Modification of noble metal surfaces: the strong affinity of the sulfur donor for noble metal surfaces makes the compound useful where a pyrimidine-terminated organic layer is required.

Brand TCI (Tokyo Chemical Industry)
CAS number 1450-85-7
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes available in standard TCI research-scale packaging; please confirm the currently listed sizes when ordering
Physical form solid, readily weighed and dissolved
Storage keep in the closed original container under the conditions stated on the manufacturer label

Store the container tightly closed in a cool, dry, well-ventilated area, away from heat sources, moisture, and incompatible materials, following the conditions given on the manufacturer label. The original supplier container is the most suitable storage vessel; if the material must be transferred, use a clean, chemically compatible, tightly sealing container that is clearly labelled with the substance name and CAS number. Weigh and handle the solid inside a fume hood to avoid inhaling dust, and wear safety glasses, gloves, and a laboratory coat throughout. Thiol-containing compounds can carry a noticeable odour, so keep the container closed when not in active use. Consult the manufacturer safety data sheet before first use and dispose of residues and contaminated consumables through your institution's chemical waste route.

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