| Identification | More | [Name]
2-Hydroxy-3-trifluoromethylpyridine | [CAS]
22245-83-6 | [Synonyms]
2-HYDROXY-3-(TRIFLUOROMETHYL)PYRIDINE
3-(TRIFLUOROMETHYL)-1,2-DIHYDROPYRIDIN-2-ONE
3-(TRIFLUOROMETHYL)-2-PYRIDONE
BUTTPARK 24\01-66
3-(Trifluoromethyl)pyridin-2-one
3-Trifluoromethyl-pyridin-2-ol
2-Hydroxy-3-(trifluoromethyl)pyridine 97%
2-Hydroxy-3-(trifluoromethyl)pyridine97%
3-(Trifluoromethyl)pyridin-2-ol, 3-(Trifluoromethyl)pyridin-2(1H)-one
3-(Trifluoromethyl)-2-pyridinone | [EINECS(EC#)]
671-273-7 | [Molecular Formula]
C6H4F3NO | [MDL Number]
MFCD00153194 | [Molecular Weight]
163.1 | [MOL File]
22245-83-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
150-153°C | [Boiling point ]
223.7±40.0 °C(Predicted) | [density ]
1.398±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
9.67±0.10(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C6H4F3NO/c7-6(8,9)4-2-1-3-10-5(4)11/h1-3H,(H,10,11) | [InChIKey]
JHDCDEHVUADNKQ-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=CC=C1C(F)(F)F | [LogP]
0.71 at 25℃ | [CAS DataBase Reference]
22245-83-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R65:Harmful: May cause lung damage if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R20/21:Harmful by inhalation and in contact with skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
UN2811 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Description]
2-hydroxy-3-(trifluoromethyl)pyridine (or 3-(Trifluoromethyl)-2-pyridone) is a trifluoromethyl substituted 2-hydroxypyridine. It is used as a synthesis intermediate for ligands and bioactive ingredients in the application of drug discovery and catalytic reactions. In catalytic reactions, the amide group of 2-pyridone binds to transition metals, forming stable 5-/6-membered ring intermediates. Hence, 2-hydroxy-3-(trifluoromethyl)pyridine is widely used as a ligand in catalytic reactions such as directed C-H activation on meta-position. In addition, the trifluoromethyl substituent of 3-(trifluoromethyl)-2-pyridone tunes its metal-binding affinity and limits the reaction site for improving regioselectivity.
| [Chemical Properties]
White powder | [Uses]
2-Hydroxy-3-trifluoromethylpyridine is a reactant in the synthesis of Pyrido[2,3-b]pyrazine, a TRPV1 antagonist . | [Synthesis]
General procedure: 2-hydroxypyridine (0.19 g, 2.0 mmol) and ferrocene (0.11 g, 0.6 mmol) were accurately weighed and placed in a dry two-necked flask and the atmosphere was replaced under argon protection. Dimethyl sulfoxide (8.0 mL), 3.0 mol/L trifluoromethyl iodine in dimethyl sulfoxide solution (2.0 mL) and 30% aqueous hydrogen peroxide solution (0.4 mL) were added sequentially to the flask, and the reaction mixture was stirred for 20 min at 40 °C to 50 °C. After completion of the reaction, the mixture was cooled to room temperature. The generation of 2-hydroxy-3-trifluoromethylpyridine was confirmed by 19F-NMR analysis using 2,2,2-trifluoroethanol as an internal standard (19F-NMR yield: 64%). Following the subsequent processing steps of Example 1, the target product 2-hydroxy-3-trifluoromethylpyridine was obtained as a white solid (0.081 g, yield: 50%). The structure of the product was determined by 1H-NMR (deuterated chloroform, δ 6.34 (dd, J = 6.9, 5.5 Hz, 1H), 7.65 (d, J = 5.6 Hz, 1H), 7.88 (d, J = 6.9 Hz, 1H), 13.25 (brs, 1H)), 13C-NMR (deuterated chloroform, δ 105.6, 120.4 (q, JCF = 31.4 Hz), 122.7 (q, JCF = 271.3 Hz), 139.2, 140.7 (q, JCF = 4.9 Hz), 161), 19F-NMR (deuterated chloroform, δ -66), and mass spectrometry (m/z: 163 [M]+) confirmed. | [References]
[1] Patent: EP2080744, 2009, A1. Location in patent: Page/Page column 7-8
[2] Journal of Fluorine Chemistry, 2010, vol. 131, # 1, p. 98 - 105 |
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