2001-93-6

Basic information

• Product Name: DITHIOURACIL
• Synonyms: Dithiouracil ,98%;2￡4-Dimercapto;Pyrimidine-2,4(1H,3H)-dithione, 2,4-Dithioxo-1,2,3,4-tetrahydropyrimidine;Dithiouracil 98%;Pyrimidine-2,4(1H,3H);PYRIMIDINE-2,4-DITHIOL;2,4-dithio-uraci;2,4-Dithioxopyrimidine
• CAS NO: 2001-93-6
• Molecular Formula: C₄H₄N₂S₂
• Molecular Weight: 144.22
• EINECS: 217-894-5
• Product Categories: PYRIMIDINE;Nucleic acids
• Mol File: 2001-93-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 279-281 °C (dec.)(lit.)
• Boiling Point: 225.6 °C at 760 mmHg
• Flash Point: 90.3 °C
• Appearance: /solid
• Density: 1.391 (estimate)
• Vapor Pressure: 0.0855mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Store Cold
• PKA: 6.55±0.20(Predicted)
• CAS DataBase Reference: DITHIOURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: DITHIOURACIL(2001-93-6)
• EPA Substance Registry System: DITHIOURACIL(2001-93-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: YR0175000
• Hazardous Substances Data: 2001-93-6(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

General Description

Dithiouracil is a potential anticancer drug and its redox mechanism and electronic absorption behavior has been investigated in a wide pH range by UV-Vis spectroscopy, cyclic voltammetry and differential pulse voltammetry.

InChI:InChI=1/C4H4N2S2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

Upstream product

• 3934-20-1 2,6-Dichloropyrimidine 
• 141-90-2 4-hydroxy-2-mercaptopyrimidine 
• 66-22-8 uracil 
• 91-17-8 decalin 
• 22536-63-6 2-chloro-4-methoxypyrimidine 
• 141-90-2 2-thiouracil 
• 17356-08-0 thiourea 

Downstream Products

• 5909-26-2 2,4-Bis(methylthio)pyrimidine 
• 89180-09-6 4-methylamino-1H-pyrimidine-2-thione 
• 333-49-3 2-thiocytosine 
• 32084-28-9 4-hydrazino-1H-pyrimidine-2-thione 
• 66-22-8 uracil 
• 104574-05-2 (R)-2-[2-{4-[1-((R)-1-Methoxycarbonyl-2-methyl-allyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-yldisulfanyl]-pyrimidin-2-yldisulfanyl}-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester 
• 104574-04-1 C₄₀H₃₈Cl₆N₆O₁₀S₄ 
• 111780-43-9 2,4-bis(4-bromobenzoylmethylthio)pyrimidine 
• 2001-93-6 2,4-dimercaptopyrimidine 
• 1642796-88-0 Cu₂(-μCl)(κ¹S,κ¹S-dithiouracil)(PPh₃)₄ 
• 1642796-89-1 Cu₂(μ-Br)(1S,κ¹S-2,4-dithiouracil)(PPh₃)₄ 
• 1476771-05-7 [Ag₂(μ-S,S-(2,4-dithiouracil))(μ-Br)(triphenylphosphine)₄] 
• 1476771-04-6 [Ag₂(μ-S,S-(2,4-dithiouracil))(μ-Cl)(triphenylphosphine)₄] 
• 1257414-40-6 [copper(I)(μ-S,S-2,4-dithiouracil)(PPh3)(iodide)] 

Relevant articles and documents

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Pyrimidine derivatives; 1. The highly regioselective 4-thionation of pyrimidine-2,4(1H,3H)-dione derivatives with Lawesson reagent

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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.

The Tautomeric Equilibria of Thio Analogues of Nucleic Acid Bases. Part 1. 2-Thiouracil: Background, Preparation of Model Compounds, and Gas-phase Proton Affinities

The preparation is reported of all four the monoalkyl derivatives of 2-thiouracil and four of the six possible dialkyl derivatives required as models for a study of the tautomeric equilibria by physical methods.Gas-phase proton affinities are determined using ion cyclotron resonance mass spectrometry, and are used to provide quantitative estimates of individual tautomer stabilities in the vapour state.These quantitative results agree well with qualitative deductions of predominant structures for the monoalkyl derivatives from i.r. spectroscopy.