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| | 2-Chloro-5-methylpyrimidine Basic information |
| | 2-Chloro-5-methylpyrimidine Chemical Properties |
| Melting point | 89-92℃ | | Boiling point | 239.2±9.0 °C(Predicted) | | density | 1.234±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Solid | | pka | -1.03±0.22(Predicted) | | color | White to Light yellow | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C5H5ClN2/c1-4-2-7-5(6)8-3-4/h2-3H,1H3 | | InChIKey | APRMCBSTMFKLEI-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC=C(C)C=N1 | | CAS DataBase Reference | 22536-61-4(CAS DataBase Reference) |
| | 2-Chloro-5-methylpyrimidine Usage And Synthesis |
| Uses | Used in organic synthesis, catalytic agent, petrochemical additive and synthetic chemistry. Also used as intermediate for pharmaceutical. | | Synthesis | Step 1. Synthesis of 2-chloro-5-methylpyrimidine
To a stirred solution of 2,4-dichloro-5-methylpyrimidine (4.00 g, 24.5 mmol) dissolved in a solvent mixture of benzene (16.0 mL) and water (40.0 mL) was added zinc powder (4.81 g, 73.6 mmol) and ammonia (8.80 mL, 24.5 mmol) sequentially at room temperature. The reaction mixture was heated and refluxed for 18 hours, then cooled to room temperature and filtered through a diatomaceous earth pad. The filtrate was extracted with ether (Et2O), and the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1) to afford the target compound 2-chloro-5-methylpyrimidine (2.44 g, 77% yield) as a yellow oil.1H NMR (400 MHz, CDCl3) δ 2.33 (3H, s), 8.47 (2H, s). | | References | [1] Patent: WO2013/132376, 2013, A1. Location in patent: Page/Page column 224
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4720 - 4744
[3] Patent: US2012/53180, 2012, A1. Location in patent: Page/Page column 8
[4] Patent: US2010/190771, 2010, A1. Location in patent: Page/Page column 33
[5] Patent: US2008/306082, 2008, A1. Location in patent: Page/Page column 26-27 |
| | 2-Chloro-5-methylpyrimidine Preparation Products And Raw materials |
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