5-Nitrouracil

Base Information

• Chemical Name: 5-Nitrouracil
• CAS No.: 611-08-5
• Molecular Formula: C4H3N3O4
• Molecular Weight: 157.086
• Hs Code.: 29335990
• European Community (EC) Number: 210-250-4
• NSC Number: 9790
• DSSTox Substance ID: DTXSID2060597
• Nikkaji Number: J1.522.742G,J27.921H
• Wikidata: Q27128575
• Metabolomics Workbench ID: 61257
• ChEMBL ID: CHEMBL323780
• Mol file: 611-08-5.mol

Synonyms:5-nitrouracil

Chemical Property of 5-Nitrouracil

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 7.81E-09mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.607
• Boiling Point: 453.3 °C at 760 mmHg
• PKA: 5.19±0.10(Predicted)
• Flash Point: 227.9 °C
• PSA: 111.54000
• Density: 1.7 g/cm³
• LogP: -0.50540
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, Water
• Water Solubility.: 3.61g/L(25 oC)
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 157.01235559
• Heavy Atom Count: 11
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

5-Nitrouracil 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, F
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 22-24/25-45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)[N+](=O)[O-]
• Uses: 5-Nitrouracil is a compound useful in organic synthesis. 5-Nitrouracil (cas# 611-08-5) is a compound useful in organic synthesis.

Technology Process of 5-Nitrouracil

There total 27 articles about 5-Nitrouracil 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) → 5-nitrobarbituric acid (611-08-5,28806-18-0)

Guidance literature:

With sulfuric acid; nitric acid; at 50 - 55 ℃; for 3h; Inert atmosphere;

DOI:10.1038/onc.2014.225

Reference yield: 50.0%

benzoin oxime (441-38-3) → 5-nitrobarbituric acid (611-08-5,28806-18-0) + benzaldehyde (100-52-7) + benzonitrile (100-47-0)

Guidance literature:

With triethylamine; 2,4-Dichloro-5-nitropyrimidine; In acetonitrile; for 5h; Product distribution; Heating;

Reference yield: 44.0%

Benzophenone oxime (574-66-3) + 2,4-Dichloro-5-nitropyrimidine (49845-33-2) → 5-nitrobarbituric acid (611-08-5,28806-18-0) + 2,4-bis-diphenyliminoxy-5-nitropyrimidine

Guidance literature:

In dichloromethane; for 0.5h; Product distribution; Ambient temperature; other solvent, temperature, reaction time;

upstream raw materials:

6-Methyluracil

4-chloro-2-ethylsulfanyl-pyrimidine

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

5-nitroorotic acid

Downstream raw materials:

5-hydroxyuracil

5-Aminouracil

1,3-dimethyl-5-nitrouracil

oxaluric acid

Refernces

• 1、 ?turala, Ji?í,Bohá?ová, Soňa,Chudoba, Josef,Metelková, Radka,Cibulka, Radek. "Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations". . p. 2676 - 2699. Retrieved 2015/03/18.
• 2、 Jain, Harsh V.,Rasheed, Roshni,Kalman, Thomas I.. "The role of phosphate in the action of thymidine phosphorylase inhibitors: Implications for the catalytic mechanism". body text. p. 1648 - 1651. Retrieved 2010/08/20.