| Identification | Back Directory | [Name]
6-CHLORO-2-IODO-3-HYDROXYPYRIDINE | [CAS]
188057-26-3 | [Synonyms]
188057-26-3
6-Chloro-2-iodopyridin-3-ol
6-Chloro-2-iodo-3-pyridinol
3-Pyridinol,6-chloro-2-iodo-
6-CHLORO-2-IODO-3-HYDROXYPYRIDINE
3-Hydroxy-6-chloro-2-iodopyridine
6-Chloro-2-iodo-3-hydroxypyridine,98%
6-CHLORO-2-IODO-3-HYDROXYPYRIDINE ISO 9001：2015 REACH | [EINECS(EC#)]
158-856-9 | [Molecular Formula]
C5H3ClINO | [MDL Number]
MFCD07636749 | [MOL File]
188057-26-3.mol | [Molecular Weight]
255.44 |
| Chemical Properties | Back Directory | [Melting point ]
191-193℃ | [Boiling point ]
333℃ | [density ]
2.219 | [Fp ]
155℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Slightly Soluble (1.3 g/L) (25°C). | [form ]
powder to crystal | [pka]
4.22±0.10(Predicted) | [color ]
White to Yellow to Green | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C5H3ClINO/c6-4-2-1-3(9)5(7)8-4/h1-2,9H | [InChIKey]
FWIMPBYPMQSSCD-UHFFFAOYSA-N | [SMILES]
C1(I)=NC(Cl)=CC=C1O |
| Hazard Information | Back Directory | [Uses]
2,2'-Dipyridylamine has been obtained by by heating a mixture of 2-aminopyridine and 2-bromo- (chloro-, iodo- ) -pyridine with anhydrous zinc chloride or with barium oxide. | [Synthesis]
Step 1: 6-Chloropyridin-3-ol (112 g, 868 mmol) was used as a raw material and dissolved in a solvent mixture of THF (800 mL) and water (800 mL). Sodium carbonate (92.0 g, 1.736 mol) and iodine (244.2 g, 1.04 mol) were subsequently added. The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the aqueous and organic phases were separated and the product was mainly present in the aqueous phase. The aqueous phase product was washed with hexane (400 mL x 2) to remove impurities. Next, the pH of the aqueous phase was adjusted to 7 with hydrochloric acid and extracted with ethyl acetate (500 mL x 4). The organic layers were combined, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the crude product, which was washed with ethyl acetate to give a final 6-chloro-2-iodopyridin-3-ol 163 g in 75% yield. The structure of the product was confirmed by 1H NMR (DMSO, 400 MHz): δ 11.13 (s, 1H, OH), 7.31 (dd, J = 8.4,12.8 Hz, 2H). | [References]
[1] Tetrahedron Letters, 2003, vol. 44, # 4, p. 725 - 728
[2] Patent: US6696439, 2004, B1. Location in patent: Page column 20
[3] Patent: WO2015/165428, 2015, A1. Location in patent: Page/Page column 18
[4] Organic Process Research and Development, 2016, vol. 20, # 7, p. 1227 - 1238
[5] Patent: US2011/76291, 2011, A1. Location in patent: Page/Page column 148 |
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