5-ethenyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 151677
• Molecular Formular: C6H6N2O2
• Molecular Mass: 138.12404
• Monoisotopic Mass: 138.04292744
• SMILES: C=Cc1c[nH]c(=O)[nH]c1=O
• Canonical SMILES: C=Cc1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C6H6N2O2/c1-2-4-3-7-6(10)8-5(4)9/h2-3H,1H2,(H2,7,8,9,10)
• InChIKey: ZRYZBEQILKESAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethenyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-ethenyl-1,3-dihydropyrimidine-2,4-dione
• Synonyms: 5-Ethenyl-2,4(1H,3H)-pyrimidinedione; NSC 208961; 5-Vinyluracil; 5-Vinyl-1H-pyrimidine-2,4-dione; 5-Vinyluracil; 5-乙烯基尿嘧啶; 5-乙烯基-1H-嘧啶-2,4-二酮; 5-乙烯尿嘧啶

Database IDs

• CAS Number: 37107-81-6
• MDL Number: MFCD00913267
• PubChem SID: 24880583; 162245827
• PubChem CID: 99305

CALCULATED PROPERTIES

• Acid pKa: 9.657928
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.31918967
• LogD (pH = 7.4): -0.32152393
• Log P: -0.31915984
• Molar Refractivity: 34.9715 cm^3
• Polarizability: 13.045832 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Pale Yellow Solid; Powder
• Melting Point: >300 °C (dec.)(lit.); 298-304°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C6H6N2O2

DETAILS

Sigma Aldrich - 570656

Packaging
250 mg in glass bottle

Toronto Research Chemicals - V625000

A new nucleoside analog active against tumor cells.

REFERENCES

• Demario, M., et al.: J. Clin. Oncol., 16, 3362 (1999)
• Grem, J., et al.: J. Clin. Oncol., 18, 3952 (1999)
• Tebbutt, N., et al.: Eur. J. Cancer, 38, 1000 (1999)
• Hattori, K., et al.: Bioorg. Med. Chem. Lett., 13, 867 (1999)