2-Chloro-6-methoxypyridine
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2-Chloro-6-methoxypyridine
structure -
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CAS No:
17228-64-7
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Formula:
C6H6ClNO
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Chemical Name:
2-Chloro-6-methoxypyridine
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Synonyms:
Pyridine,2-chloro-6-methoxy-;2-Chloro-6-methoxypyridine;6-Chloro-2-methoxypyridine;2-Methoxy-6-chloropyridine
- Categories:
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CAS No:
Characteristics
22.1
3
Colorless to pale yellow liquid
1.207 g/mL at 25 °C(lit.)
185.5 °C
169 °F
n20/D 1.528(lit.)
0.832mmHg at 25°C
Safety Information
III
2810
3
36/37/38
26-36/37/39-37/39
Xi
Irritant
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Chloro-6-methoxypyridine Use and Manufacturing
To a stirred solution of 2, 6-dichloropyridine (8) (68.9 g, 466 mmol) in MeOH (500 mL) was added NaOMe (100 g, 1.86 mol) at room temperature. The resulting mixture was stirred at 60°C for 24 h. After cooling, the mixture was quenched with 2 Maqueous HCl, and extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford 9(66.9 g, quant) as a colorless oil.9: IR (film, cm−1): 1599, 1585, 1560, 1468, 1410, 1302, 1265, 1152, 1024, 876, 789; 1H-NMR (CDCl3, 500 MHz) δ: 7.51 (t, J=7.37 Hz, 1H), 6.90 (d, J=7.37 Hz, 1H), 6.65 (d, J=7.37 Hz, 1H), 3.94 (s, 3H); 13C-NMR (CDCl3, 125 MHz) δ: 163.9, 148.4, 140.5, 116.2, 109.1, 54.0; HR-MS (ESI-time-of-flight (TOF)): Calcd for C6H7ClNO [(M+H)+] 144.0211. Found 144.0211.Add 2, 6-dichloropyridine, methanol, and sodium hydroxide in the corresponding proportions in Table 1 to a 250 ml or 500 ml three-necked flask equipped with a reflux condenser, stirrer, and thermometer, and heat to 70-75°C with stirring. While maintaining reflux, the reaction was sampled separately for 1 hour, 3 hours, and 5 hours. The conversion of 2, 6-dichloropyridine was measured and the reaction product was 6-chloro-2-methoxypyridine.Table 1 Composition of 2, 6-dichloropyridine, Methanol, and NaOH in Examples 1-20In a 500 ml reaction flask, 29.6 g of 2, 6-dichloropyridine was added, 8 g of solid sodium hydroxide and 200 ml of methanol, Stirring began to heat up to reflux, the reaction time was 8 hours, Stop the reaction, steamed most of the methanol, cooled, add 100 ml of water, Extract once with dichloromethane, remove methylene chloride to give the crude product, The crude product was distilled under reduced pressure to give 2-methoxy-6-chloropyridine, The yield is 88percent.
Computed Properties
Molecular Weight:143.57
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:143.0137915
Monoisotopic Mass:143.0137915
Topological Polar Surface Area:22.1
Heavy Atom Count:9
Complexity:89.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of 2-Chloro-6-methoxypyridine
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