| Identification | More | [Name]
2-IODO-3-HYDROXYPYRIDINE | [CAS]
40263-57-8 | [Synonyms]
2-IODO-3-HYDROXYPYRIDINE
2-IODO-3-PYRIDINOL
2-IODOPYRIDIN-3-OL
3-HYDROXY-2-IODOPYRIDINE
3-Pyridinol, 2-iodo-
Pyridine, 2-iodo-3-hydroxy-
2-HYDROXY-3-IODOPYRIDINE | [EINECS(EC#)]
254-864-0 | [Molecular Formula]
C5H4INO | [MDL Number]
MFCD00023421 | [Molecular Weight]
221 | [MOL File]
40263-57-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
193-195°C | [Boiling point ]
296.6±20.0 °C(Predicted) | [density ]
2.142±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
4.74±0.10(Predicted) | [color ]
White to tan | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Light Sensitive | [BRN ]
109836 | [InChI]
InChI=1S/C5H4INO/c6-5-4(8)2-1-3-7-5/h1-3,8H | [InChIKey]
HJBGMPCMSWJZNH-UHFFFAOYSA-N | [SMILES]
C1(I)=NC=CC=C1O | [CAS DataBase Reference]
40263-57-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Uses]
2-Iodo-3-hydroxypyridine acts as a reagent in the synthesis of the differentiating antibiotic azatyrosine | [Synthesis]
General procedure for the synthesis of 2-iodo-3-hydroxypyridine using 3-hydroxypyridine as starting material: sodium carbonate (Na2CO3, 11.6 g, 109.72 mmol) and iodine (I2, 13.3 g, 52.57 mmol) were added sequentially to a solution of 3-hydroxypyridine (5.0 g, 52.57 mmol) in water (400 mL). The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the pH was adjusted to 4 with 1 M hydrochloric acid (HCl) solution. the precipitate was collected by filtration, washed with cold water and dried to give 2-iodo-3-hydroxypyridine (10.7 g, 92% yield) as a white powder. The product characterization data were as follows: melting point 189-190 °C (neat); thin layer chromatography (TLC) Rf = 0.33 (unfolding reagent dichloromethane/ethanol, 97/3, v/v); infrared spectroscopy (IR, KBr pressed) νmax (cm-1): 2851, 2722, 2573, 2345, 1560, 1455, 1301, 1189, 1121, 794, 668; nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, DMSO-d6): δ10.88 (s, 1H, OH), 7.87 (dd, 1H, J1 = 1.6 Hz, J2 = 4.4 Hz, H-6), 7.24 (dd, 1H, J1 = 4.4 Hz, J2 = 8.0 Hz, H-5), 7.18 (dd, 1H, J1 = 1.6 Hz, J2 = 8.0 Hz, H-4); nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, DMSO-d6): δ 154.0, 141.8, 124.3, 121.3, 110.9; high resolution mass spectrometry (HRMS) calculated value of C5H4INO [M + H]+ 221.9410, measured value 221.9416. | [References]
[1] Tetrahedron Letters, 2012, vol. 53, # 8, p. 944 - 947
[2] Tetrahedron, 2017, vol. 73, # 41, p. 6000 - 6007
[3] Patent: CN107793420, 2018, A. Location in patent: Paragraph 0009
[4] Roczniki Chemii, 1936, vol. 16, p. 502,507
[5] Chem. Zentralbl., 1937, vol. 108, # I, p. 3634 |
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