15422-05-6

Basic information

• Product Name: 6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione
• Synonyms: 6-phenylthiouracil
• CAS NO: 15422-05-6
• Molecular Formula: C₁₀H₈N₂O₂S
• Molecular Weight: 220.2477
• Mol File: 15422-05-6.mol
• Article Data: 8

Chemical Properties

• Density: 1.43g/cm³
• Refractive Index: 1.683
• CAS DataBase Reference: 6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione(15422-05-6)
• EPA Substance Registry System: 6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione(15422-05-6)

Safety Data

• Hazardous Substances Data: 15422-05-6(Hazardous Substances Data)

Upstream product

• 4270-27-3 6-chlorouracil 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 4270-27-3 6-chloro-2,4-dihydroxypyrimidine 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 209908-56-5 trans-1-(4'-chloro-2'-buten-1'-yl)-6-(thiophenyl)uracil 
• 209908-62-3 cis-1-(4'-chloro-2'-buten-1'-yl)-6-(thiophenyl)uracil 
• 209908-68-9 1-(4'-chloro-2'-butyn-1'-yl)-6-(thiophenyl)uracil 
• 81077-94-3 5-bromo-6-phenylthiouracil 
• 80947-57-5 6-phenylthio-5-formyluracil 
• 152039-46-8 4-Phenylsulfanyl-2,6-bis-trimethylsilanyloxy-pyrimidine 

Relevant articles and documents

Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study

In this study, three new 6-(arylthio)uracil derivatives, namely, 6-(phenylthio)pyrimidine-2,4(1H,3H)-dione (1), C10H8N2O2S; 6-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione (2), C11H10N2O2S; and 6-(3,5-dimethylphenylthio)pyrimidine-2,4(1H,3H)-dione (3), C12H12N2O2S, have been synthesized. Single-crystal structures of these compounds reveal an invariant molecular tape contains alternate R22(8) synthons formed by N-H···O hydrogen bonds in 1 and 3. This alternate hydrogen-bonded pattern disappeared in 2; instead, a new synthon is generated. The lattice energy calculation suggests that the methyl-substituted derivatives (2 and 3) have high stabilization energy than compound 1. The electrostatic potential map reveals the difference in the accepting tendency of the carbonyl oxygen. The Hirshfeld surface and 2D-fingerprint plots analyses demonstrate that the major intermolecular interactions come from H···O contacts in 1, and these contacts were reduced due to the presence of methyl substitutions in 2 and 3. This reduction is compensated by the increase of the same amount of H···H contacts in these structures. Further, the PIXEL energy and DFT calculations at the M06-2X-D3/cc-pVTZ level of theory were used to characterize the dimeric topology formed in structures of 1-3. The intermolecular interaction energies of dimers calculated by the PIXEL method were compared with the B97D3/def2-TZVP level of approximation. Although these molecules' crystal packing is somewhat different, the energy frameworks show similarities on the respective crystal structure's shortest axis. Furthermore, the nature and strength of various noncovalent interactions such as N-H···O, C-H···O/S/π, π···π, and a chalcogen bond of type C-S···O═C were evaluated using the Bader's quantum theory of atoms-in-molecules framework.

Synthesis of substituted uracils by the reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles under focused microwave irradiation

Under microwave irradiation, the nucleophilic substitution reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to th

Synthesis and anti-HIV activity of acyclic unsaturated C6- and C5-thiophenyl uracil nucleoside and nucleotide analogues

Acyclic unsaturated C6- and C5-thiophenyl uracil nucleosides and nucleotides, analogues of 1[(2-hydroxyethoxy)methyl]6-(phenylthio)thymine (HEPT), were designed, synthesized and investigated as potential anti-HIV-1 agents in ATH8 cel