2-Chloro-5-nitropyridin-4-amine
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2-Chloro-5-nitropyridin-4-amine
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CAS No:
2604-39-9
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Formula:
C5H4ClN3O2
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Chemical Name:
2-Chloro-5-nitropyridin-4-amine
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Synonyms:
2-Chloro-5-nitropyridin-4-amine;2-Chloro-4-aMino-5-nitropyridine;4-Amino-2-chloro-5-nitro-pyridine;2-Chloro-5-nitro-pyridin-4-ylamine
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CAS No:
Characteristics
84.7
1.5
white to light yellow crystal powder
1.6±0.1 g/cm3
155-156 °C
388.5°C at 760 mmHg
188.7±26.5 °C
1.658
0mmHg at 25°C
Safety Information
Xn
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Chloro-5-nitropyridin-4-amine Use and Manufacturing
2-ChloiO-4-nitroaminopyridine (10.0 g, mol) was carefully dissolved in 100 mL of concentrated sulfuric acid at room temperature and heated 100 A solution of 2, 4-dichloro-5-nitropyridine (3 g, 15 mmol) in methanolic ammonia (15 mL) was stirred at 25-28°C for 18 h. The reaction mixture was concentrated by evaporation in vacuo, then the residue was isolated by filtration and purified by hexane wash (3 x 30 mL), to provide the title compound (2.3 g, 86percent) as a yellow solid. H (400MHz, DMSO-d6) 8.83 (s, 1H), 7.35 (br s, 2H), 7.03 (s, 1H). LCMS (ES+) 173.95 (M+H), RT 1.46 minutes.To a solution of 2-chloropyridin-4-amine (10 g, 78 mmol) in conc. sulfuric acid (60 mL) at 0° C. was slowly added fuming nitric acid (30 mL). The mother liquor was purified on SiO2 gel column (30 g) by elution with (Tolune-EtOAc, (85:15) affording the desired minor isomer 4 (11.0 g, 9percent). 1H NMR (DMSO-d6; 500 MHz): delta 8.83 (1H, s), 8.10 (1H, brs), 6.95 (1H, s); EIMS m/z: 174.8 (M+1), 172.8 (M-1).The compound To a solution of NBS (564 mg, 3.17 mmol) was added to a solution of 1 (500 mg, 2.88 mmol) in 8 mL of AcOH. The resulting mixture was stirred at 60 C for 4 h. After cooled to room temperature, the mixture was diluted with water. The precipitate was collected by filtration to afford 580 mg of 2 as a yellow solid, which was used in the next step without further purification. [M+Hj : 251.91, 253.96.
Computed Properties
Molecular Weight:173.56
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:172.9992041
Monoisotopic Mass:172.9992041
Topological Polar Surface Area:84.7
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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