3-Bromo-2-chloro-5-nitropyridine
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3-Bromo-2-chloro-5-nitropyridine
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CAS No:
5470-17-7
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Formula:
C5H2BrClN2O2
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Chemical Name:
3-Bromo-2-chloro-5-nitropyridine
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Synonyms:
Pyridine,3-bromo-2-chloro-5-nitro-;3-Bromo-2-chloro-5-nitropyridine;NSC 26278
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CAS No:
Safety Information
IRRITANT
2811
1
25-41
26-39-45
Xi,T
Irritant
P280-P301 + P310-P305 + P351 + P338
H301-H318
|Danger|H301 (90.7%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P280, P301+P310, P305+P351+P338, P310, P321, P330, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-Bromo-2-chloro-5-nitropyridine Use and Manufacturing
Second step POCI3 (3 ml) was added at 0°C to the mixture of compound 2 (7.25 g, 33 mmol) and quinoline (2 ml, 16.5 mmol). This reaction medium was heated at 12000 for 2.5 hours and then, after cooling to room temperature, 20 ml of water were added. The precipitate formed was collected by filtration and dried to give the expected compound 3 in the form of a brown solid, in a yield of 95percent (7.5 g).The NMR analyses (1H 400 MHz DMSO-d6) are in accordance with the expected structure.Step 2: To a cooled (0-5° C.) mixture of 3-bromo-2-hydroxy-5-nitropyridine (47 g; 0.214 mol) and quinoline (13.7 g; 0.107 mol) was added POClTo a cooled (0-5° C.) mixture of 3-bromo-2-hydroxy-5-nitropyridine (47.0 g, 0.214 mol) and quinoline (13.7 g, 0.107 mol) was added POClStep 2: To a cooled (0-5° C.) mixture of 3-bromo-2-hydroxy-5-nitropyridine (47.0 g; 0.214 mol) and quinoline (13.7 g; 0.107 mol) was added POClUnder ice-cooling, to a solid mixture of 3-bromo-5-nitro-2-ol (21.4 mmol) and quinoline (10.7Mmol) was slowly added dropwise phosphorus oxychloride (27.8 mmol). The mixture was stirred at 120 ° C for 3.5 hours, cooled to to 100 ° C, was added 10 ml of water. The reaction was stirred vigorously in an ice water bath for 1 hour. The precipitate was collected by filtration, washed with water, and dried to give 4.15 g of the title compound. 1H-NMR (CD30D) S9.09 (lH, d, J = 2.4Hz), 8.40 (lH, d, J = 2.4Ηζ).2-Chloro-3-bromo-5-nitropyridine (5.8 g, 24.4 mmol, CAS: 5470-17-7) and cesium carbonate (9.6 g, 29.5 mmol) were suspended in 20 mL of dimethyl sulfoxide and added to 4 , 4-difluorocyclohexanol (4.0 g, 29.4 mmol), heated to 80 C for 1 h, cooled to room temperature, then water and ethyl acetate layered, the organic phase, washed with brine, anhydrous sodium sulfate Drying and concentration in vacuo gave intermediate M-28-1 (3.5 g).2-Chloro-3-bromo-5-nitropyridine (3.0 g, 12.6 mmol, CAS: 5470-17-7) and cesium carbonate (8.4 g, 25.8 mmol) were suspended in cyclohexanol (10 mL, CAS: 108) -93-0), Heat to 100 C for 4 h, cool to room temperature, add water and ethyl acetate layerThe organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated.Intermediate M-7-1 (3.5 g) was obtained.2-Chloro-3-bromo-5-nitropyridine (10.0 g, 42.1 mmol, CAS: 5470-17-7), Aniline (4.3 g, 46.2 mmol, CAS: 62-53-3), cesium carbonate (18.0 g, 55.2 mmol) was suspended in 100 mL of dimethyl sulfoxide, heated to 80 C for 2 h, cooled to room temperature, then added with water and The ethyl acetate was layered, and the organic phase was washed with saturated brine.Dry over anhydrous sodium sulfate, concentrate by vacuum, and purified by column chromatography.Intermediate M-6-1 (5.4 g) was obtained.
Computed Properties
Molecular Weight:237.44
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Exact Mass:235.89882
Monoisotopic Mass:235.89882
Topological Polar Surface Area:58.7
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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3-Bromo-2-chloro-5-nitropyridine
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