2,4-Dihydroxypyrimidine-5-carboxylic acid CAS 23945-44-0
2,4-Dihydroxypyrimidine-5-carboxylic acid Basic information
| Product Name: | 2,4-Dihydroxypyrimidine-5-carboxylic acid |
| Synonyms: | 1,2,3,4-TETRAHYDRO-2,4-DIOXO-5-PYRIMIDINECARBOXYLIC ACID;2,4-DIHYDROXYPYRIMIDINE-5-CARBOXYLIC ACID;5-CARBOXY-2,4-DIHYDROXYPYRIMIDINE;5-CARBOXYURACIL extrapure;2,4-Dioxo-11,2,3,4-tetrahydropyrimidine-5-carboxylic acid;2,4-Dioxo-1H-pyrimidine-5-carboxylic acid;5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo-;1,2,3,6-Tetrahydro-2,6-dioxo-5-pyrimidinecarboxylic acid |
| CAS: | 23945-44-0 |
| MF: | C5H4N2O4 |
| MW: | 156.1 |
| EINECS: | 245-947-2 |
| Product Categories: | Heterocycle-Pyrimidine series;Bases & Related Reagents;Nucleotides;Carboxylic Acids;Pyrazines, Pyrimidines & Pyridazines;Carboxylic Acids;Pyrazines, Pyrimidines & Pyridazines;Pyridine;Nucleotides and Nucleosides |
| Mol File: | 23945-44-0.mol |
2,4-Dihydroxypyrimidine-5-carboxylic acid Chemical Properties
| Melting point | 283 °C (dec.)(lit.) |
| Boiling point | 280.29°C (rough estimate) |
| density | 1.6814 (rough estimate) |
| refractive index | 1.4800 (estimate) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Soluble in DMSO |
| pka | 5.08±0.20(Predicted) |
| form | Crystalline Powder |
| color | White to slightly yellow |
| Water Solubility | 1.8g/L(20 ºC) |
| InChI | InChI=1S/C5H4N2O4/c8-3-2(4(9)10)1-6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) |
| InChIKey | ZXYAAVBXHKCJJB-UHFFFAOYSA-N |
| SMILES | C1(=O)NC=C(C(O)=O)C(=O)N1 |
| CAS DataBase Reference | 23945-44-0(CAS DataBase Reference) |
| EPA Substance Registry System | 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo- (23945-44-0) |
Safety Information
| Risk Statements | 36/37/38 |
| Safety Statements | 24/25 |
| WGK Germany | 3 |
| TSCA | TSCA listed |
| HS Code | 29335990 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | white to slightly yellow crystalline powder or |
| Uses | 2,4-Dihydroxypyrimidine-5-carboxylic acid (Uracil-5-carboxylic acid) has been used for the visual sensing of melamine (at parts-per-billion (ppb) level) by a highly sensitive analytical method based on Au nanoparticles. |
| Definition | ChEBI: Uracil-5-carboxylic acid is a pyrimidinemonocarboxylic acid that is uracil carrying a carboxy group at position 5. It is functionally related to a uracil. It is a conjugate acid of a uracil-5-carboxylate. It is a tautomer of a 2,4-dihydroxypyrimidine-5-carboxylic acid. |
| General Description | 2,4-Dihydroxypyrimidine-5-carboxylic acid (Uracil-5-carboxylic acid) has been obtained from 5-formyluracil by the action of enzyme, thymine 7-hydroxylase. It has been used to synthesize N1-alkylated uracil derivatives. |
| Synthesis | 65-71-4 23945-44-0 The general procedure for synthesizing uracil-5-carboxylic acid from 5-methyluracil was as follows: 100 g of 5-methyluracil and 300 mL of deionized water were added to an autoclave reactor, followed by the addition of 35 mL of a 30% hydrogen peroxide solution. Next, 15 g of 1-hydroxy-1,2,3-benzotriazin-4(3H)-one and 35 g of a pre-prepared catalyst (as described in Example 3) were added. The atmosphere in the autoclave was replaced with oxygen and the reaction system was subsequently heated to 130°C and maintained at this temperature for 3 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure and poured into an ice-water mixture for cooling and crystallization, resulting in 150 g of white solid product. The yield of this step was 96.1%, and the purity of the product was 99.3% as analyzed by high performance liquid chromatography (HPLC). |
| References | [1] Patent: CN108341785, 2018, A. Location in patent: Paragraph 0014-0020 [2] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038 [3] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038 |
2,4-Dihydroxypyrimidine-5-carboxylic acid Preparation Products And Raw materials
| Raw materials | Ethanol-->Sodium hydroxide-->Sodium-->Urea-->Triethyl orthoformate-->Diethyl malonate-->5-Hydroxymethyluracil-->2,4-DIMETHOXY-5-PYRIMIDINECARBOXYLIC ACID-->ETHYL N-(2-CYANO-3-ETHOXYACRYLOYL)CARBAMATE-->5-Cyanouracil-->Thymine |
| Preparation Products | isopropanyl 2,4-dichloropyriMidine-5-carboxylate-->5-FORMYLURACIL |
