5-Nitrouracil CAS 611-08-5
5-Nitrouracil Basic information
| Product Name: | 5-Nitrouracil |
| Synonyms: | NITROURACIL;2,4-Dihydroxy-5-nitropyrimidin;5-NITRO-2,4-DIHYDROXYPYRIMIDINE;5-NITROPYRIMIDINE-2,4(1H,3H)-DIONE;5-NITROPYRIMIDINE-2,4-DIOL;5-NITROURACIL;NSC 9790;NHCONHCOC(NO 2):CH |
| CAS: | 611-08-5 |
| MF: | C4H3N3O4 |
| MW: | 157.08 |
| EINECS: | 210-250-4 |
| Product Categories: | marker;Pyrimidine;Nucleic acids;Bases & Related Reagents;Nucleotides;Functional Materials;Organic Nonlinear Optical Materials;Nucleotides and Nucleosides;Pyrimidines;Pyrimidine series;Pyridines, Pyrimidines, Purines and Pteredines;Miscellaneous;611-08-5 |
| Mol File: | 611-08-5.mol |
5-Nitrouracil Chemical Properties
| Melting point | >300 °C(lit.) |
| Boiling point | 281.7°C (rough estimate) |
| density | 1.8278 (rough estimate) |
| refractive index | 1.5000 (estimate) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | DMSO, Water |
| pka | 5.19±0.10(Predicted) |
| form | Crystalline Powder or Needles |
| color | Off-white to pale yellow |
| Water Solubility | 3.61g/L(25 ºC) |
| BRN | 10410 |
| InChI | InChI=1S/C4H3N3O4/c8-3-2(7(10)11)1-5-4(9)6-3/h1H,(H2,5,6,8,9) |
| InChIKey | TUARVSWVPPVUGS-UHFFFAOYSA-N |
| SMILES | C1(=O)NC=C([N+]([O-])=O)C(=O)N1 |
| CAS DataBase Reference | 611-08-5(CAS DataBase Reference) |
| EPA Substance Registry System | 5-Nitrouracil (611-08-5) |
Safety Information
| Hazard Codes | F,C |
| Risk Statements | 11-34 |
| Safety Statements | 22-24/25-45-36/37/39-26-16 |
| WGK Germany | 2 |
| RTECS | UV9104545 |
| TSCA | TSCA listed |
| HS Code | 29335990 |
| Storage Class | 13 - Non Combustible Solids |
| Uses | 5-Nitrouracil is a compound useful in organic synthesis. |
| Chemical Properties | Off-White Solid |
| Uses | 5-Nitrouracil (cas# 611-08-5) is a compound useful in organic synthesis. |
| Definition | ChEBI: 5-nitrouracil is a C-nitro compound consisting of uracil having a nitro group at the 5-position. It is functionally related to a uracil. |
| Synthesis | 66-22-8 611-08-5 The general procedure for the synthesis of 5-nitropyrimidine-2,4(1H,3H)-dione from pyrimidine-2,4(1H,3H)-dione: Nitric acid solution (5.34 mL, 120 mmol, 70% solution) was added drop-wise to concentrated sulfuric acid (19.7 mL, 360 mmol, 98% solution) under the condition of the temperature not exceeding 50 ℃. Subsequently, pyrimidine-2,4(1H,3H)-dione (7.204 g, 60 mmol) was added to the stirred mixed acid solution in batches while controlling the reaction temperature not to exceed 50°C. The reaction mixture was heated to 55 °C and maintained for 3 h, after which it was cooled below room temperature and the reaction was quenched with ice water (38 mL). The resulting white precipitate was collected by filtration, washed with a small amount of ice water and dried under reduced pressure at 55 °C to afford 5-nitropyrimidine-2,4(1H,3H)-dione (8.658 g, 55.11 mmol, 92% yield) as a white solid. Product properties: decomposition temperature >288°C; thin layer chromatography Rf value 0.00 (unfolding agent ratio 1:10 ethyl acetate/hexane); IR spectrum (ZnSe pool, solid) vmax: 3142-2811 cm^-1 (medium, broad, OH/NH/CH), 1732 cm^-1 (strong, C=O), 1677 and 1624 cm^-1 (strong. NO2), 1417 cm^-1 (medium, CH), 1356 cm^-1 (medium, NO2), 1318 cm^-1 (strong, aromatic R2NH/R3N), 1234 cm^-1 (strong, -OH), 975 and 832 cm^-1 (weak, aromatic ring bending); 1H NMR (500 MHz, d6-DMSO): δ 8.84 ( 1H, single peak, 6-CH) ppm; 13C NMR (125 MHz, d6-DMSO): δ 155.5 (4-C=O), 149.8 (6-CH), 147.9 (2-C=O), 125.1 (5-CNO2) ppm. |
| Purification Methods | The uracil recrystallises in prisms from boiling H2O as the monohydrate and loses H2O on drying in vacuo. [UV: Brown J Chem Soc 3647 1959, Brown J Appl Chem 2 239 1952, Johnson J Am Chem Soc 63 263 1941, Beilstein 24 I 313, 24 II 171, 24 III/IV 1236.] |
| References | [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 29 - 34 [2] American Chemical Journal, 1905, vol. 33, p. 443 [3] American Chemical Journal, 1908, vol. 40, p. 31 [4] Journal of Biological Chemistry, 1908, vol. 4, p. 410 [5] Journal of the American Chemical Society, 1919, vol. 41, p. 786 |
5-Nitrouracil Preparation Products And Raw materials
| Raw materials | Uracil |
| Preparation Products | 2-CHLORO-5-NITROPYRIMIDIN-4-AMINE-->2-Chloro-4,5-diaminopyrimidine-->2-METHOXY-5-NITROPYRIMIDIN-4-AMINE-->5-Aminouracil-->2,4-Dichloro-5-nitropyrimidine-->2,4,5-TRIHYDROXYPYRIMIDINE |
