Uracil

Base Information

• Chemical Name: Uracil
• CAS No.: 24897-50-5
• Deprecated CAS: 144104-68-7,42910-77-0,4433-21-0,4433-24-3,766-19-8,138285-60-6,153445-42-2,51953-19-6,138285-60-6,153445-42-2,42910-77-0,4433-24-3,51953-19-6,766-19-8
• Molecular Formula: C4H3 D N2 O2
• Molecular Weight: 113.09
• European Community (EC) Number: 200-621-9
• NSC Number: 759649,29742,3970
• UNII: 56HH86ZVCT
• DSSTox Substance ID: DTXSID4021424
• Nikkaji Number: J4.842I
• Wikipedia: Uracil
• Wikidata: Q182990
• NCI Thesaurus Code: C917
• Metabolomics Workbench ID: 37192
• ChEMBL ID: CHEMBL566
• Mol file: 24897-50-5.mol

Synonyms:Uracil

Chemical Property of Uracil

Chemical Property:

• Boiling Point: 440.5°Cat760mmHg
• Flash Point: 220.2°C
• PSA: 65.72000
• Density: 1.321g/cm³
• LogP: -0.93680
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.027277375
• Heavy Atom Count: 8
• Complexity: 161

Purity/Quality:

99% ^*data from raw suppliers

Uracil-d ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=CNC(=O)NC1=O
• Recent ClinicalTrials: Study of 0.1% Uracil Topical Cream (UTC) for the Prevention of Hand-Foot Syndrome
• Recent EU Clinical Trials: Onderzoek naar de farmacokinetiek van uracil na orale toediening bij pati?nten met colorectaal carcinoom.
• Recent NIPH Clinical Trials: A phase II trial of uracil ointment for the prevention of capecitabine induced hand-foot syndrome (HFS): .
• Uses: Uracil-d can be used to treat Hepatitis C, HSV, RSV, HCV, and as an anti-tumor agent.

Technology Process of Uracil

There total 4 articles about Uracil 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: 99.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → uracil-5-d (24897-50-5)

Guidance literature:

With water-d2; triethylamine; at 70 ℃; for 288h; Inert atmosphere;

DOI:10.1021/ja206163j

Reference yield: 80.0%

5-iodouracil (696-07-1) → uracil-5-d (24897-50-5) + Uracil-5,6-d2 (24897-52-7)

Guidance literature:

With deuterium; tris(triphenylphosphine)ruthenium(II) chloride; In N,N-dimethyl-formamide; at 69.9 ℃; under 750.06 Torr; Product distribution; var. catalysts, var. solvents;

Reference yield:

1,3,5-trideuterio-1H-pyrimidine-2,4-dione → uracil-5-d (24897-50-5)

Guidance literature:

With water; Heating;

DOI:10.1016/0584-8539(84)80073-2

upstream raw materials:

5-iodouracil

uracil

Downstream raw materials:

1,3,5,6-tetradeuterio-1H-pyrimidine-2,4-dione

Refernces

• 1、 Ragab, Amany E.,Grueschow, Sabine,Tromans, Daniel R.,Goss, Rebecca J. M.. "Biogenesis of the unique 4′,5′-dehydronucleoside of the uridyl peptide antibiotic pacidamycin". supporting information; experimental part. p. 15288 - 15291. Retrieved 2011/11/11.
• 2、 Rocek, Josef,Svata, Vladimir,Leseticky, Ladislav. "HOMOGENEOUS HYDROGENOLYSIS OF THE C-I BOND; PREPARATION OF 2H>URACIL". . p. 1244 - 1248. Retrieved 2007/10/02.