Introduction：Basic information about 5-Chlorouracil CAS 1820-81-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
5-Chlorouracil Basic information
| Product Name: | 5-Chlorouracil |
| Synonyms: | TIMTEC-BB SBB004103;2,4(1H,3H)-Pyrimidinedione,5-chloro-;2,4-Pyrimidinediol,5-chloro-;3h)-pyrimidinedione,5-chloro-4(1h;5-Chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione;5-Chloropyrimidine-2,4-diol;5-Chlorouracil,99%;Fluorouracil Related CoMpound E |
| CAS: | 1820-81-1 |
| MF: | C4H3ClN2O2 |
| MW: | 146.53 |
| EINECS: | 217-339-7 |
| Product Categories: | Pyrimidine series;Heterocyclic Compounds;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Heterocycles;Nucleotides;PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines |
| Mol File: | 1820-81-1.mol |
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5-Chlorouracil Chemical Properties
| Melting point | >300 °C (lit.) |
| density | 1.6838 (rough estimate) |
| refractive index | 1.6550 (estimate) |
| storage temp. | 2-8°C |
| solubility | 1 M NH4OH: soluble50mg/mL |
| pka | 6.77±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| Water Solubility | 2.501g/L(25 ºC) |
| BRN | 127173 |
| InChI | InChI=1S/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
| InChIKey | ZFTBZKVVGZNMJR-UHFFFAOYSA-N |
| SMILES | C1(=O)NC=C(Cl)C(=O)N1 |
| CAS DataBase Reference | 1820-81-1(CAS DataBase Reference) |
| EPA Substance Registry System | 5-Chlorouracil (1820-81-1) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-36-26 |
| RIDADR | UN2811 |
| WGK Germany | 3 |
| RTECS | YQ9410000 |
| HazardClass | 6.1 |
| HS Code | 29335995 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral
Muta. 2 |
5-Chlorouracil Usage And Synthesis
| Description | 5-Chlorouracil (5-CU) may have advantages for the inhibition of undesired fibroblast proliferation taking place after surgery for glaucoma and results in filtration failure. A comparison of 5-CU and 5-fluorouracil (5-FU) cytotoxicity shows that 5-CU is approximately 1000 times less toxic to nonproliferative cells while maintaining good antimitotic activity. In addition, 5-CU induces apoptotic-controlled cell death, whereas the influence of 5-FU is by apoptonecrosis. The 5-CU apoptotic mechanism is driven mainly by the nuclear translocation of AIF and activation of the LEI/L-DNase II pathways, which are caspase-independent. In conclusion, even though 5-CU is a weaker antiproliferating agent than 5-FU, its reduced toxic side effects on the epithelium and sclera allow for its enhanced efficacy and extended reduction of IOP after filtering surgery for glaucoma. 5-CU is an effective mutagen, clastogen and toxicant, and an effective inducer of sister-chromatid exchange, and is not as sensitive to ionizing radiation as other thymine analogues[1]. |
| Chemical Properties | white to light beige crystalline powder |
| Uses | 5-Chlorouracil was used as a control in resazurin-based cytotoxicity assay for screening of cytotoxicity in hepatocytes and liver cell lines. |
| Uses | 5-Chlorouracil can be used for the experimental and clinical treatment of neoplastic and viral diseases. |
| Definition | ChEBI: An organochlorine compound consisting of uracil having an chloro substituent at the 5-position. It is functionally related to a uracil. |
| General Description | The shape resonance spectra of 5-chlorouracil, obtained from fixed-nuclei elastic scattering calculations by the Schwinger multichannel method with pseudopotentials, was studied. |
| Purification Methods | It recrystallises from hot H2O (4g/500mL) using charcoal. [McOmie et al. J Chem Soc 3478 1955, West & Barrett J Am Chem Soc 76 3146 1954, Beilstein 24 III/IV 1231.] |
| References | [1] Marianne Berdugo Polak. “Controlled delivery of 5-chlorouracil using poly(ortho esters) in filtering surgery for glaucoma.” Investigative ophthalmology & visual science (2008): 2993–3003. |
5-Chlorouracil Preparation Products And Raw materials
| Preparation Products | 2,4,5-Trichloropyrimidine |
