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| | 2,4-Dichloro-5-pyrimidinecarbonyl chloride Basic information |
| Product Name: | 2,4-Dichloro-5-pyrimidinecarbonyl chloride | | Synonyms: | 2,4-Dichloro-5-pyrimidinecarbonylchloride;5-(Chlorocarbonyl)-2,4-dichloropyrimidine, 5-(Chloroformyl)-2,4-dichloropyrimidine;2,4-DichloropyriMidine-5-carbonyl chloride 97%;5-(Chlorocarbonyl)-2,4-dichloropyrimidine;2,3-Dichloro-5-pyrimidine carbonyl chloride;5-(Chlorocarbonyl)-2,4-dichlo;5-Pyrimidinecarbonyl chloride, 2,4-dichloro-;RSYY（Avanafil)-46 | | CAS: | 2972-52-3 | | MF: | C5HCl3N2O | | MW: | 211.43 | | EINECS: | 638-925-2 | | Product Categories: | Pyrimidine;Building Blocks;pharmacetical;Pyrimidine series;Pyrimidines;Heterocycle-Pyrimidine series | | Mol File: | 2972-52-3.mol |  |
| | 2,4-Dichloro-5-pyrimidinecarbonyl chloride Chemical Properties |
| Boiling point | 83 °C(Press: 0.05 Torr) | | density | 1.645 g/mL at 25 °C | | refractive index | n20/D1.586 | | Fp | 93℃ | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | pka | -5.08±0.29(Predicted) | | form | liquid | | color | Clear, colourless | | InChI | InChI=1S/C5HCl3N2O/c6-3-2(4(7)11)1-9-5(8)10-3/h1H | | InChIKey | DZTIFMWYYHCREC-UHFFFAOYSA-N | | SMILES | C(Cl)(C1=CN=C(Cl)N=C1Cl)=O | | CAS DataBase Reference | 2972-52-3(CAS DataBase Reference) |
| Hazard Codes | C,Xi | | Risk Statements | 20/21/22-34 | | Safety Statements | 6-7/9-24/25-26-36/37/39-51 | | RIDADR | 3265 | | WGK Germany | 3 | | HazardClass | IRRITANT, CORROSIVE | | PackingGroup | Ⅲ | | HS Code | 2933599590 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Dam. 1
Skin Corr. 1B |
| | 2,4-Dichloro-5-pyrimidinecarbonyl chloride Usage And Synthesis |
| Synthesis | The general procedure for the synthesis of 2,4-dichloro-5-pyrimidinecarbonyl chloride from uracil-5-carboxylic acid is as follows:
9.1 Preparation of 2,4-dihydroxypyrimidine-5-carbonyl chloride
In a 250 mL round bottom flask, 10.0 g (64.0 mmol) of 2,4-dihydroxypyrimidine-5-carboxylic acid was dissolved in 46 mL (500.0 mmol) of phosphorus oxychloride (POCl3) under nitrogen protection. The reaction mixture was cooled to 0°C via an ice bath, followed by the batch addition of 47.7 g (230 mmol) phosphorus pentachloride (PCl5). The reaction solution was heated and stirred at reflux for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 100 mL of toluene and ground, followed by filtration. After this operation was repeated three times, the filtrate was evaporated under reduced pressure to give 13.5 g (64.0 mmol) of the yellow oily product 2,4-dichloro-5-pyrimidinecarbonyl chloride, which was used directly in the next step of the reaction. Yield = 100%. | | References | [1] Patent: US2011/251194, 2011, A1. Location in patent: Page/Page column 21
[2] Patent: US2010/222319, 2010, A1. Location in patent: Page/Page column 18
[3] Patent: WO2015/21149, 2015, A1. Location in patent: Page/Page column 56; 57
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2746 - 2763
[5] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 55 |
| | 2,4-Dichloro-5-pyrimidinecarbonyl chloride Preparation Products And Raw materials |
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