2-Thiouracil

Base Information

• Chemical Name: 2-Thiouracil
• CAS No.: 141-90-2
• Deprecated CAS: 107646-88-8,107646-89-9,156-82-1,4401-53-0,4401-54-1,107646-89-9,156-82-1,4401-54-1
• Molecular Formula: C4H4N2OS
• Molecular Weight: 128.155
• Hs Code.: 29335995
• European Community (EC) Number: 205-508-8
• NSC Number: 758660,19473
• UNII: 59X161SCYL
• DSSTox Substance ID: DTXSID4021347
• Nikkaji Number: J9.741A
• Wikipedia: 2-Thiouracil
• Wikidata: Q20892027
• NCI Thesaurus Code: C29856
• Metabolomics Workbench ID: 66965
• ChEMBL ID: CHEMBL345768
• Mol file: 141-90-2.mol

Synonyms:Thiouracil

Chemical Property of 2-Thiouracil

Chemical Property:

• Appearance/Colour: white to cream fine crystalline powder
• Vapor Pressure: 5.45E-05mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.677
• Boiling Point: 337.2 °C at 760 mmHg
• PKA: pKa 7.46 (Uncertain)
• Flash Point: 157.7 °C
• PSA: 80.74000
• Density: 1.46 g/cm³
• LogP: 0.43250
• Storage Temp.: 2-8°C
• Solubility.: 7.9g/l
• Water Solubility.: 0.5 g/L
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.00443393
• Heavy Atom Count: 8
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

2-Thiouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 40-45-20/21/22
• Safety Statements: 36/37-53-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=S)NC1=O
• Uses: Reagent used in the preparation of Antithyroid agents. antiviral, thyroid depressant 2-Thiouracil has been used in the synthesis and characterization of silver colloid and film substrates and their applications in surface-enhanced Raman scattering (SERS)

Technology Process of 2-Thiouracil

There total 33 articles about 2-Thiouracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

3-acetyl-2-methylsulfanyl-3H-pyrimidin-4-one (283168-85-4) → 2-thiouracil (141-90-2,156-82-1)

Guidance literature:

With pyridine; hydrogen sulfide; triethylamine; for 4h;

Reference yield: 74.0%

5-(dihydroxyboryl)-1,3-dimethyluracil → 4-hydroxy-2-mercaptopyrimidine (141-90-2,80275-68-9)

Guidance literature:

With sodium ethanolate; thiourea; In ethanol;

DOI:10.1021/jm00105a049

Reference yield: 72.0%

thiourea (17356-08-0) + orthoformic acid triethyl ester (122-51-0) + Polymer: 4-phenylbutan-2-one cyclic malonic acid ester, bound to Merrifield resin → 2-thiouracil (141-90-2,156-82-1)

Guidance literature:

orthoformic acid triethyl ester; Polymer: 4-phenylbutan-2-one cyclic malonic acid ester, bound to Merrifield resin; for 6h; Heating;

thiourea; for 12h; Heating;

at 220 - 240 ℃; for 0.333333h; Further stages.;

DOI:10.1021/jo020175m

upstream raw materials:

2-ethylthio-3H-pyrimidin-4-one

(3t-ethoxy-acryloyl)-thiourea

ethyl 3,3-diethoxypropanoate

thiourea

Downstream raw materials:

2-(benzylsulfanyl)pyrimidin-4(3H)-one

(3Ξ,6R)-8,7'-dioxo-7t-(2-phenyl-acetylamino)-7'H-spiro[5-thia-1-aza-bicyclo[4.2.0]octane-3,3'-thiazolo[3,2-a]pyrimidine]-2ξ-carboxylic acid

2-phenyl-2,3-dihydro-thiazolo[3,2-a]pyrimidin-5-one

NSC295404

Refernces

• 1、 Alexeev,Sivets,Safonova,Mikhailov. "Substrate specificity of E. coli uridine phosphorylase. Further evidences of high-syn conformation of the substrate in uridine phosphorolysis". . p. 107 - 121. Retrieved 2017.
• 2、 Xu, Jianfeng,Tsanakopoulou, Maria,Magnani, Christopher J.,Szabla, Rafa?,?poner, Judit E.,?poner, Ji?í,Góra, Robert W.,Sutherland, John D.. "A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization". . p. 303 - 309. Retrieved 2017/04/03.