| Identification | More | [Name]
2-AMINO-5-IODO-3-NITROPYRIDINE | [CAS]
25391-57-5 | [Synonyms]
2-AMINO-5-IODO-3-NITROPYRIDINE
5-IODO-3-NITRO-PYRIDIN-2-YLAMINE
2-PYRIDINAMINE,5-IODO-3-NITRO | [Molecular Formula]
C5H4IN3O2 | [MDL Number]
MFCD04038464 | [Molecular Weight]
265.01 | [MOL File]
25391-57-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
215-219 °C (lit.) | [Boiling point ]
365.4±42.0 °C(Predicted) | [density ]
2.229±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
solid | [pka]
0.41±0.49(Predicted) | [Appearance]
Light yellow to yellow Solid | [CAS DataBase Reference]
25391-57-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Uses]
2-Amino-5-iodo-3-nitropyridine is used in the synthetic preparation of disubstituted pyridinyl azabicyclo heptanes as epibatidine analogs. These analogs are evaluated for its affinity for nicotinic acetylcholine receptors via in vitro and antinociceptive properties via in vivo in rats. | [Synthesis]
To a 250 mL three-necked flask were added 2-amino-3-nitropyridine (10.0 g, 72.0 mmol), acetic acid (44 mL) and water (10 mL). The mixture was heated to 90°C and then periodic acid (3.28 g, 14.4 mmol) and concentrated sulfuric acid (1.3 mL) at a mass percent concentration of 98% were added sequentially. After stirring for 10 min, iodine (9.1 g, 36.0 mmol) was added and stirring was continued for 60 min at this temperature. Upon completion of the reaction, the reaction solution was cooled to room temperature and subsequently poured into saturated aqueous sodium thiosulfate solution (100 mL). The solid product was separated by filtration and washed sequentially with saturated brine (50 mL x 2) and petroleum ether (50 mL x 2). The crude product was recrystallized using a mixed solvent of petroleum ether and ethyl acetate (5:1, v/v) to afford a high purity yellow solid 2-amino-5-iodo-3-nitropyridine (17.57 g, 69.1 mmol, 96% yield). | [References]
[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[2] Patent: CN107325045, 2017, A. Location in patent: Paragraph 0006; 0009
[3] Patent: WO2013/53983, 2013, A1. Location in patent: Page/Page column 37
[4] Patent: US2015/11548, 2015, A1. Location in patent: Paragraph 0152 |
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