133039-83-5

Basic information

• Product Name: 2,4-Pyrimidinedithiol (9CI)
• Synonyms: 2,4-Pyrimidinedithiol (9CI)
• CAS NO: 133039-83-5
• Molecular Formula: C4H4N2S2
• Molecular Weight: 144.21796
• Product Categories: PYRIMIDINE
• Mol File: 133039-83-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Pyrimidinedithiol (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pyrimidinedithiol (9CI)(133039-83-5)
• EPA Substance Registry System: 2,4-Pyrimidinedithiol (9CI)(133039-83-5)

Safety Data

• Hazardous Substances Data: 133039-83-5(Hazardous Substances Data)

Usage

General Description

2,4-Pyrimidinedithiol (9CI) is a chemical compound with the molecular formula C4H4N2S2. It is a heterocyclic organic compound containing a pyrimidine ring and two thiol groups attached to carbon atoms 2 and 4 of the ring. 2,4-Pyrimidinedithiol (9CI) has potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science. It is known for its ability to form coordination complexes with various metal ions, making it useful in catalysis and metal ion sensing. Additionally, 2,4-Pyrimidinedithiol (9CI) is also used as a building block in the synthesis of more complex organic compounds. Overall, this chemical compound has versatile properties that make it valuable in different industrial and research applications.

Upstream product

• 3934-20-1 2,6-Dichloropyrimidine 
• 141-90-2 4-hydroxy-2-mercaptopyrimidine 
• 2001-93-6 2,4-dithiouracil 

Downstream Products

• 136129-70-9 bis{copper(I)(dithiouracil)(triphenylphosphine)chloride} 
• 136129-66-3 bis{copper(I)(dithiouracil)(tri-p-tolylphosphine)chloride} 
• 5909-26-2 2,4-Bis(methylthio)pyrimidine 

Relevant articles and documents

Spectroscopic identification of 2,4-pyrimidinedithiol; an experimental matrix isolation and ab initio Hartree-Fock and density functional theory study

2,4-Pyrimidinedithiol (the dithiol form of 2,4-dithiouracil) was generated by UV (λ > 335 nm) irradiation of the dithione form of 2,4-dithiouracil isolated in low-temperature argon or nitrogen matrices. The IR and UV spectra of the photoproduct are reported. The dithiol form of 2,4-dithiouracil was identified by comparison of the experimental spectrum with the spectrum theoretically predicted for this form at the HF/6-31 (d,p) and DFT(B-3LYP)/6-31 (d,p) levels. This comparison resulted also in assignment of the bands observed in the IR spectrum of 2,4-pyrimidinedithiol to the theoretically predicted normal modes.

Chalcogen containing heterocyclic scaffolds: New hybrids with antitumoral activity

In this work, 27 novel hybrid derivatives containing diverse substituents with chalcogen atoms (selenium or sulfur) and several active heterocyclic scaffolds have been synthesized. Compounds were tested against two human cancer cells lines (MCF7 and PC-3) and a normal human mammary epithelial cell line (184B5) in order to determine their activity and selectivity against malignant cells. Ten compounds showed GI50values below 10?μM in at least one of the cancer cell lines and six of them exhibited a selectivity index higher than 9. In general, selenium-containing compounds were more active than their corresponding sulfur analogs but we found some thiocyanate derivatives with comparable or higher activity and selectivity. Among the different substituents, the seleno- and thio-cyanate groups showed the most promising results. On the basis of their potent activity and high selectivity index, compounds 7e and 8f (containing a thiocyanate and a selenocyanate group, respectively) were selected for further biological evaluation. Both the compounds induced caspase-dependent cell death and cell cycle arrest in G2/M phase. In addition, these compounds do not violate any of the Lipinski's Rule of Five and thus possess good potential to become drugs, compound 7e being particularly promising.