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| | 4,6-Dichloro-2-(methylsulfonyl)pyrimidine Basic information |
| Product Name: | 4,6-Dichloro-2-(methylsulfonyl)pyrimidine | | Synonyms: | nsc 45040;PYRIMIDINE, 4,6-DICHLORO-2-(METHYLSULFONYL)-;VITAS-BB TBB000242;DLMSP;4,6-DICHLORO-2-(METHYLSULFONYL)PYRIMIDINE;4,6-DIMETHY-2-METHYLSULFONYLPYRIMIDINE;2-(methylsulfonyl)-4,6-dichloropyrimidine;4,6-DICHLORO-2-METHANESULFONYLPYRIMIDINE | | CAS: | 4489-34-3 | | MF: | C5H4Cl2N2O2S | | MW: | 227.07 | | EINECS: | | | Product Categories: | Heterocycle-Pyrimidine series;Boron, Nitrile, Thio,& TM-Cpds;Heterocycles | | Mol File: | 4489-34-3.mol |  |
| | 4,6-Dichloro-2-(methylsulfonyl)pyrimidine Chemical Properties |
| Melting point | 117-118°C | | Boiling point | 402.3±48.0 °C(Predicted) | | density | 1.604 | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | soluble in Methanol | | form | powder to crystal | | pka | -9.08±0.30(Predicted) | | color | White to Yellow to Orange | | InChI | InChI=1S/C5H4Cl2N2O2S/c1-12(10,11)5-8-3(6)2-4(7)9-5/h2H,1H3 | | InChIKey | DROUVIKCNOHKBA-UHFFFAOYSA-N | | SMILES | C1(S(C)(=O)=O)=NC(Cl)=CC(Cl)=N1 | | CAS DataBase Reference | 4489-34-3(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36 | | Safety Statements | 26-24/25 | | HS Code | 29335990 |
| | 4,6-Dichloro-2-(methylsulfonyl)pyrimidine Usage And Synthesis |
| Chemical Properties | White solid | | Synthesis | The general procedure for the synthesis of 4,6-dichloro-2-(methylsulfonyl)pyrimidines from 4,6-dichloro-2-methylthioalkylpyrimidines is as follows:
Example 27: Synthesis of 4,6-dichloro-2-(methylsulfonyl)pyrimidine
Commercially available 4,6-dichloro-2-methylsulfanylpyrimidine (Aldrich, 21.0 g, 107.0 mmol, 1 eq.) was dissolved in dichloromethane and cooled in an ice bath. Subsequently, 3-chloroperoxybenzoic acid (60.0 g, 77% wt, 268.0 mmol, 2.5 eq.) was added in batches. The resulting white suspension was stirred at room temperature for 4 hours. Upon completion of the reaction, it was washed sequentially with a mixture of 1 M sodium thiosulfate solution and saturated sodium bicarbonate solution (1:1, v/v, 200 mL x 3), saturated sodium bicarbonate solution (100 mL x 3) and brine (100 mL x 1). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was dried under high vacuum overnight to give the title compound EPO27 as a white solid (22.0 g, 91% yield). Thin layer chromatography Rf value was 0.20 (unfolding agent: 20% ethyl acetate/hexane); mass spectrum m/z 227 (calculated value 227, corresponding to molecular formula C5H4Cl2N2O2S+). | | References | [1] Patent: WO2007/14250, 2007, A2. Location in patent: Page/Page column 17-18
[2] Patent: WO2007/87245, 2007, A2. Location in patent: Page/Page column 27
[3] Patent: WO2007/87246, 2007, A2. Location in patent: Page/Page column 27
[4] Patent: WO2008/13807, 2008, A2. Location in patent: Page/Page column 6
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8153 - 8157 |
| | 4,6-Dichloro-2-(methylsulfonyl)pyrimidine Preparation Products And Raw materials |
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