5-Fluoro-1,3-dimethyluracil - ≥98% , CAS No.3013-92-1

CAS: 3013-92-1 Cat. No.: F339065 Molecular Weight: 158.13

GRADE & PURITY ≥98%

Synonyms

5-fluoro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione | EU-0068355 | 5-Fluoro-1,3-dimethyluracil, 99% | SR-01000402018-1 | 5-fluoro-1,3-dimethylpyrimidine-2,4-dione | A899578 | 5-Fluoro-1,3-dimethyluracil | NSC379683 | NSC-379683 | SCHEMBL3189250 | DTXSID90321

Storage

Room temperature

Shipped In

Normal

Overview

Oxidation of 5-fluoro-1,3-dimethyluracil (5-FDMU) with m-chloroperbenzoic acid has been described. It is reported as antineoplastic drug. On photoirradiation, 5-fluoro-1,3-dimethyluracil yields the trans-anti cyclobutane dimer and the cis-syn cyclobutane dimer. UV irradiation of 5-FDMU and naphthalene in a protic medium affords 5-(1-naphthyl)uracil, while in aprotic media it undergoes stereoselective 1,4-cycloaddition reaction to give a barrelene derivative. The thermochemical parameters of 5-FDMU has been determined. It reacts with substituted benzenes in the presence of trifluoroacetic acid to generate 5-aryl-1,3-dimethyluracils via photosubstitution.

Application：

Regioselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones；To synthesize 5-bis(ethoxycarbonyl)methyl-1,3-dimethyluracil；To synthesize new highly conjugated propenylidene derivatives via aromatic Paterno-Buchi type cycloaddition with 1-methoxynaphthalene

Specifications

Synonyms

5-fluoro-1, 3-dimethylpyrimidine-2, 4(1H, 3H)-dione | EU-0068355 | 5-Fluoro-1, 3-dimethyluracil, 99% | SR-01000402018-1 | 5-fluoro-1, 3-dimethylpyrimidine-2, 4-dione | A899578 | 5-Fluoro-1, 3-dimethyluracil | NSC379683 | NSC-379683 | SCHEMBL3189250 | DTXSID90321

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488189546
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189546
• Canonical Smiles: CN1C=C(C(=O)N(C1=O)C)F
• IUPAC Name: 5-fluoro-1,3-dimethylpyrimidine-2,4-dione
• InChIKey: DDEWVRFHURYTHA-UHFFFAOYSA-N
• INCHI: 1S/C6H7FN2O2/c1-8-3-4(7)5(10)9(2)6(8)11/h3H,1-2H3
• Isomeric SMILES: CN1C=C(C(=O)N(C1=O)C)F
• WGK Germany: 3
• Molecular Weight: 158.13
• Reaxy-Rn: 880396
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=880396&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Halopyrimidines
• Alternative Parents: Pyrimidones Hydropyrimidines Aryl fluorides Vinylogous amides Heteroaromatic compounds Ureas Lactams Azacyclic compounds Organooxygen compounds Organonitrogen compounds Organofluorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Halopyrimidine - Pyrimidone - Aryl fluoride - Aryl halide - Hydropyrimidine - Heteroaromatic compound - Vinylogous amide - Lactam - Urea - Azacycle - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CCRF-CEM (65223 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 158.130 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 158.049 Da
• Monoisotopic Mass: 158.049 Da
• Topological Polar Surface Area: 40.600 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 249.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Hanwen Liu, Ying Liu, Ting Zhou, Penghui Zhou, Jianguo Li, Anping Deng.  (2022)  Ultrasensitive and Specific Detection of Anticancer Drug 5-Fluorouracil in Blood Samples by a Surface-Enhanced Raman Scattering (SERS)-Based Lateral Flow Immunochromatographic Assay.  MOLECULES,  27  (13): (4019).  [PMID:35807264] [10.3390/molecules27134019]

2. Ting Zhou, Guangzhao He, Changjia Hu, Kang Wu, Ying Liu, Jianguo Li, Anping Deng.  (2022)  Development of a highly sensitive and specific monoclonal antibody-based ELISA coupled with immuno-affinity extraction for the detection of anticancer drug 5-fluorouracil in blood samples.  TALANTA,      [PMID:35696979] [10.1016/j.talanta.2022.123655]