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| | 2-Chloro-4-methoxypyridine Basic information |
| | 2-Chloro-4-methoxypyridine Chemical Properties |
| Boiling point | 224-225 °C (lit.) | | density | 1.258 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.5400(lit.) | | Fp | >230 °F | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Soluble in alcohol. | | form | Liquid | | pka | 2.25±0.10(Predicted) | | Specific Gravity | 1.258 | | color | Colorless to pale yellow | | BRN | 1423379 | | InChI | InChI=1S/C6H6ClNO/c1-9-5-2-3-8-6(7)4-5/h2-4H,1H3 | | InChIKey | PMTPFBWHUOWTNN-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC=CC(OC)=C1 | | CAS DataBase Reference | 17228-69-2(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37 | | RIDADR | 2810 | | WGK Germany | 3 | | PackingGroup | III | | HS Code | 29333990 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-Chloro-4-methoxypyridine Usage And Synthesis |
| Chemical Properties | Colorless liquid | | Uses | 2-Chloro-4-methoxypyridine may be used to synthesize:
- 2-(2′,4′-difluorophenyl)-4-methoxypyridine
- (2-chloro-4-methoxypyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methanol
- (2-chloro-4-methoxypyridin-3-yl)bis-[2-(methylsulfanyl) pyrimidin-4-yl]methyl acetate
| | Uses | It is an active pharmaceutical ingredient. | | General Description | 2-Chloro-4-methoxypyridine can be obtained from the reaction between 2-chloro-4-nitropyridine and sodium methoxide in the presence of dioxane. It can also be prepared starting from 4-methoxy-2(1H)-pyridone and 4-nitropyridine N-oxide. | | Synthesis | At room temperature, 4-tert-butylpyridine (5.5 mL, 5.08 g, 37.5 mmol, Aldrich) was dissolved in acetic acid (30 )
mL, Fluka). Hydrogen peroxide was added (30% aqueous solution, 11.5 mL, containing 3.83 g H2O2, 113
mmol, excess, Fluka.). The reaction mixture was stirred at 80 C overnight. It was rotor evaporated to 1/3 of its volume, neutralized with aqueous Na2CO3 and extracted several times with CH2Cl2. The organic layer was evaporated to dryness. The starting material (0.2-1.0% CH3OH in CH2Cl2) was removed and the product (5-7% CH3OH in CH2Cl) was recovered by chromatographic purification (run twice; silica, 2 x 25 g). 2-chloro-4-methoxypyridine. The reaction was carried out in dry DMF under argon. At room temperature, sodium methanol (190) was added to the reaction.
mg, 3.52 mmol, excess, Fluka) was added to 2-chloro-4-nitropyridine (500 mg, 3.15
mmol, Aldrich) in DMF immediately undergoes an exothermic reaction and the color of the mixture changes from light yellow to dark red. Stirring for 3 h at room temperature gave a brown suspension which was extracted with water and ether. The organic layer was washed with water to remove the DMF. purification by chromatography (silica, 10 g; CH2Cl2) afforded the colorless oily product 2-chloro-4-methoxypyridine: 393
mg (2.74 mmol, 87%). |
| | 2-Chloro-4-methoxypyridine Preparation Products And Raw materials |
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