6-chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 10087
• Molecular Formular: C4H3ClN2O2
• Molecular Mass: 146.53182
• Monoisotopic Mass: 145.98830503
• SMILES: [nH]1c(=O)[nH]c(=O)cc1Cl
• Canonical SMILES: Clc1cc(=O)[nH]c(=O)[nH]1
• InChI: InChI=1S/C4H3ClN2O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H2,6,7,8,9)
• InChIKey: PKUFNWPSFCOSLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 6-chloro-1,3-dihydropyrimidine-2,4-dione
• Synonyms: 6-Chloro-2,4-pyrimidinediol; 6-Chloropyrimidine-2,4(1H,3H)-dione; NSC 210419; NSC 43265; 6-Chlorouracil; 4-Chloro-2,6-dihydroxypyrimidine; 6-Chloro-2,4-dihydroxypyrimidine; 4-CHLOROURACIL; 6-Chloropyrimidine-2,4(1H,3H)-dione; 4-Chlorouracil; 6-Chloro-2,4(1H,3H)-pyrimidinedione; 6-Chlorouracil; 4-Chlorouracil; 6-Chlorouracil; 6-氯尿嘧啶

Database IDs

• CAS Number: 4270-27-3
• EC Number: 224-258-0
• MDL Number: MFCD00014595
• Beilstein Number: 120492
• PubChem SID: 160973394; 24893168
• PubChem CID: 73272

CALCULATED PROPERTIES

• Acid pKa: 7.747433
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.18840155
• LogD (pH = 7.4): -0.3449292
• Log P: -0.18597978
• Molar Refractivity: 40.8195 cm^3
• Polarizability: 11.625988 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White Solid
• Melting Point: >293°C (dec.); 300 °C; 301-302°C(dec); 301-302(dec.)(subl.)°C; ca 295°C dec.
• Partition Coefficient: -0.012

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 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%; ≥99%; 95%; 98%; 98+%

DETAILS

MP Biomedicals - 02190322

(6-Chlorouracil)

Sigma Aldrich - C9525

Application
Chlorouracil (4-Chlorouracil; 6-Chlorouracil) is a halogenated uracil that is useful in studies of the effects of halogenation on nucleic acid base-pair stability and alkali metal ion affinity.Reaction of 6-chlorouracil with 4-(dimethylamino)pyridine, 4-methylpyridine, and pyridin-4-yl-morpholine yielded pyridinium-substituted uracils as chlorides which were converted into pyridinium uracilates by deprotonation. These heterocyclic mesomeric betaines are cross-conjugated and thus possess separate cationic (pyridinium) and anionic (uracilate) moieties. Calculations and X-ray single crystal analyses may be used to characterize these systems and to compare the salts with the betaines.

Toronto Research Chemicals - C423780

6-Chlorouracil acts as an inhibitor of yeast alcohol dehydrogenase (ADH-H). 6-Chlorouracil is a potential inhibitor of DNA repair glycosylases.

REFERENCES

• Gauri, K.K.: Arch. Pharm., 306, 622 (1973)
• Speina, E. et al.: Acta Biochim. Pol., 52, 167 (1973)