4-Thiouracil

Base Information

• Chemical Name: 4-Thiouracil
• CAS No.: 591-28-6
• Molecular Formula: C4H4N2OS
• Molecular Weight: 128.155
• Hs Code.: 29335990
• European Community (EC) Number: 627-565-1
• NSC Number: 43288
• DSSTox Substance ID: DTXSID50207840
• Nikkaji Number: J579.678D
• Wikipedia: 4-Thiouracil
• Wikidata: Q20892040
• Metabolomics Workbench ID: 123891
• ChEMBL ID: CHEMBL1650608
• Mol file: 591-28-6.mol

Synonyms:4-thiouracil

Chemical Property of 4-Thiouracil

Chemical Property:

• Appearance/Colour: yellow powder
• Melting Point: 295 °C
• Refractive Index: 1.7000 (estimate)
• Boiling Point: 388 °C at 760 mmHg
• PKA: 5.38±0.20(Predicted)
• Flash Point: 188.4 °C
• PSA: 84.81000
• Density: 1.46 g/cm³
• LogP: 0.47090
• Solubility.: 1 M NaOH: soluble50mg/mL
• XLogP3: -0.5
• 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:

98%,99%, ^*data from raw suppliers

4-Thiouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CNC(=O)NC1=S
• Description: 4-Thiouracil is a site-specific, photoactivatable probe used to detect RNA structures and nucleic acid-nucleic acid contacts. It absorbs ultraviolet light >300 nm and, in the presence of oxygen, acts as an energy donor to produce singlet oxygen by triplet-triplet energy transfer. The highly reactive oxygen species then reacts readily with 4-thiouracil, leading to the production of uracil and uracil-6-sulfonate, which is fluorescent at a wavelength of ~390 nm. 4-Thiouracil is used as a T. gondii uracil phosphoribosyltransferase substrate to produce 4-thiouridine monophosphate, which can ultimately be incorporated into RNA.
• Uses: 4-Thiouracil is suitable reagent employed in Schneider′s media for the embryos during RNA extraction. It may be employed as reagent for the Northwestern blotting technique. 4-Thiouracil is a derivative of Uracil (U801000), which is a nitrogenous base in RNA nucleic acid. 4-Thiouracil is used for tagging in cell type-specific RNA isolation from intact complex tissues.

Technology Process of 4-Thiouracil

There total 8 articles about 4-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: 92.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 4-thiouracil (591-28-6)

Guidance literature:

With diphosphorus pentasulfide; sodium hydrogencarbonate; In diethylene glycol dimethyl ether; at 110 ℃; for 2h;

DOI:10.1055/s-1987-27906

Reference yield: 77.5%

1-Benzoyl-4-thiouracil (215544-47-1) → 4-thiouracil (591-28-6)

Guidance literature:

With methylamine; In ethanol; for 1.5h; Ambient temperature;

DOI:10.1039/a803878c

Reference yield:

4-methylsulfanylpyrimidin-2(1H)-one (35551-31-6) → 4-thiouracil (591-28-6) + Cytosine (71-30-7)

Guidance literature:

With diammonium sulfide; In water; at 70 ℃; for 16h;

DOI:10.1039/C8CC09435G

upstream raw materials:

uracil

1-Benzoyl-4-thiouracil

4-thiouridine

4-methylsulfanylpyrimidin-2(1H)-one

Downstream raw materials:

uracil

2-(3-fluorobenzylthio)pyrimidin-4-ol

2-(benzylthio)pyrimidin-4-ol

4-methylsulfanylpyrimidin-2(1H)-one

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 2017/02/05.
• 2、 Frieden, Miriam,Giraud, Matthieu,Reese, Colin B.,Song, Quanlai. "Synthesis of 1-[cis-3-(hydroxymethyl)cyclobutyl]-uracil, -thymine and -cytosine". . p. 2827 - 2832. Retrieved 2007/10/03.