3,5-Diiodo-4-hydroxypyridine Chemical Properties

Boiling point:

342.0±37.0 °C(Predicted)

Density 

2.769

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.36±0.23(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C5H3I2NO/c6-3-1-8-2-4(7)5(3)9/h1-2H,(H,8,9)

InChIKey

FRPFEVLOFNAKBS-UHFFFAOYSA-N

SMILES

C1=NC=C(I)C(O)=C1I

3,5-Diiodo-4-hydroxypyridine Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-hydroxy-3,5-diiodopyridine from pyridin-4(1H)-one: In a 3L three-necked round-bottomed flask, pyridin-4(1H)-one (50.0 g, 0.50 mol) and N-iodosuccinimide (232 g, 1.00 mol) were suspended in acetonitrile (1L). The reaction mixture was refluxed for 3 hours. After completion of the reaction, the mixture was cooled in an ice bath and subsequently filtered and washed with acetonitrile (150 mL). The resulting light yellow solid was dried under reduced pressure at 60 °C for 15 h to give 165 g (95% yield) of 4-hydroxy-3,5-diiodopyridine as a light yellow solid.LC/MS (Method B): retention time 1.34 min, (M+H)+ m/z 348.

References

[1] Patent: WO2015/144290, 2015, A1. Location in patent: Page/Page column 69
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 1078 - 1101
[3] DRP/DRBP Org.Chem.,
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 765
[5] Journal of the Society of Chemical Industry, London, 1943, vol. 62, p. 189

3,5-Diiodo-4-hydroxypyridine(7153-08-4)Related Product Information

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• Methyl 4-hydroxyquinoline-6-carboxylate
• 8-FLUORO-4-HYDROXYQUINOLINE
• 3-Bromo-4-hydroxy-5-nitropyridine
• 4-Hydroxy-6-methoxyquinoline-3-carbonitrile
• 4-HYDROXY-5-BROMOQUINOLINE
• 4-Hydroxy-3-methyl-1H-indazole
• 4-HYDROXY-7-NITROQUINOLINE
• 1-Methylazepan-4-ol
• Benzaldehyde, 4-hydroxy-2-iodo-
• 3-iodopyridin-4-ol
• 5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• 2-Pyridinecarboxylic acid, 4-hydroxy-, methyl ester (9CI)
• 5-IODO-1H-PYRIMIDIN-4-ONE
• 4-Hydroxy-2-pyridinecarboxylic acid ethyl ester
• Pyridin-2-ol
• 2-Aminopyridin-4-ol
• 4-IODO-PYRIDIN-3-OL