| Identification | Back Directory | [Name]
2-AMINO-5-CHLORO-3-IODOPYRIDINE | [CAS]
211308-81-5 | [Synonyms]
5-chloro-3-iodo-2-pyridinamine
5-Chloro-3-iodopyridin-2-amine
2-AMINO-5-CHLORO-3-IODOPYRIDINE
2-amino-3-iodo-5-chloropyridine
2-AMINO-5-CHLORO-4-IODOPYRIDINE
2-PyridinaMine, 5-chloro-3-iodo-
5-CHLORO-3-IODO-PYRIDIN-2-YLAMINE
2-AMINO-5-CHLORO-3-IODOPYRIDINE ISO 9001：2015 REACH | [Molecular Formula]
C5H4ClIN2 | [MDL Number]
MFCD07644578 | [MOL File]
211308-81-5.mol | [Molecular Weight]
254.46 |
| Chemical Properties | Back Directory | [Melting point ]
137-138°C | [Boiling point ]
306.9±42.0 °C(Predicted) | [density ]
2.139±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
powder to crystal | [pka]
2.27±0.49(Predicted) | [color ]
Light yellow to Yellow to Orange | [Sensitive ]
Light Sensitive | [CAS DataBase Reference]
211308-81-5 |
| Hazard Information | Back Directory | [Uses]
2-Amino-5-chloro-3-iodopyridine is a useful synthetic intermediate. It was used in the rational design of highly selective spleen tyrosine kinase inhibitors. It was also used to synthesize azaindole derivatives with antibacterial and antifungal activities. | [Synthesis]
GENERAL STEPS: 24,150 mL of a solvent mixture of tetrahydrofuran and 50 L of ethylene dichloride were added to an 8000 mL reactor, a plug-in thermometer was installed and a mechanical stirrer was started. Subsequently, 6037.5 g of 2-amino-5-chloropyridine and 18528 g of N-iodosuccinimide were added to the reactor. The reaction mixture was stirred continuously at 53 °C for 7 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and gas chromatography (GC) to confirm the complete reaction of 2-amino-5-chloropyridine. Upon completion of the reaction, the solvent was removed using a rotary evaporator to give the crude product. The crude product was recrystallized by a solvent mixture of ethyl acetate and ethanol to obtain purified 2-amino-3-iodo-5-chloropyridine. The product was dried and the calculated yield was 90.10% and the purity was 98.2% by GC. | [References]
[1] Patent: CN104744353, 2017, B. Location in patent: Paragraph 0017-0031
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 2, p. 307 - 315
[3] Patent: US2014/18533, 2014, A1. Location in patent: Paragraph 0074; 0075
[4] Patent: WO2011/73263, 2011, A1. Location in patent: Page/Page column 88-89
[5] Patent: WO2005/95400, 2005, A1. Location in patent: Page/Page column 345-346 |
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