Basic information
- CAS
22245-83-6- Standard SMILES
O=c1[nH]cccc1C(F)(F)F- InChIKey
JHDCDEHVUADNKQ-UHFFFAOYSA-N- Molecular formula
- C6H4F3NO
- Average molar mass
- 163.1 g/mol
- Monoisotopic mass
- 163.02449824
Names & identifiers
- Preferred name
- 2(1H)-Pyridinone, 3-(trifluoromethyl)-
- IUPAC
- 3-(trifluoromethyl)-1H-pyridin-2-one
- English name
- 2-Hydroxy-3-trifluoromethylpyridine
- Molecular formula
- C6H4F3NO
- Molecular weight
- 163.1
Names & synonyms
3-(trifluoromethyl)pyridin-2-ol2(1H)-PYRIDINONE, 3-(TRIFLUOROMETHYL)-RefChem:439776671-273-7948-667-522245-83-62-Hydroxy-3-Trifluoromethylpyridine2-Hydroxy-3-(trifluoromethyl)pyridine3-(trifluoromethyl)-1H-pyridin-2-one2-Hydroxy-3-Trifluoromethyl Pyridine3-(Trifluoromethyl)-2-pyridone3-(Trifluoromethyl)pyridin-2(1H)-one
Show more names
3-Trifluoromethyl-pyridin-2-olBUTTPARK 24\01-662-Hydroxy-3-(trifL2-Hydroxy-3-trifluorHydroxy-3-trifluoromethyl2-Hydroxy-3-trifluoromethyl3-trifluoroMethyl-2-pyridinol3-(Trifluoromethyl)pyridin-2-one
MFCD001531943-(TRIFLUOROMETHYL)-2(1H)-PYRIDINONEFD2043CS-W002444DS-0797FS-11282-hydroxy-3-(trifluoromethyl)-pyridineAC-20524
Database identifiers
- CAS
22245-83-6- PubChem CID
- 3678411
- DTXSID
DTXSID80394934- UNII
- 2L4XZF8FMB
- EC Number
- 671-273-7、948-667-5
- Nikkaji
- J1.900.513E、J3.791.080E
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 29.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 239
Physicochemical properties
- Melting point
- 150 · 150-153°C
- Boiling point
- 223.7 · 223.7±40.0 °C(Predicted)
- Density
- 1.398 · 1.398±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- form
- powder to crystal
- pka
- 9.67 · 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 · 0.71 at 25℃
- CAS DataBase Reference
- 22245 · 22245-83-6(CAS DataBase Reference)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Commission Regulation No 844/2012
Status: Cease Manufacture Update: 06-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/30477
Hazard Classes and Categories
Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (66.7%)
Skin Irrit. 2 (100%)；Eye Irrit. 2A (100%)
Regulatory information
Regulatory Information
Commission Regulation No 844/2012
Status: Cease Manufacture Update: 06-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/30477
Safety data
Chemistry & industry
Uses & manufacturing
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
Applications
Description2-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.
Uses2-Hydroxy-3-trifluoromethylpyridine is a reactant in the synthesis of Pyrido[2,3-b]pyrazine, a TRPV1 antagonist .
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
63 records
Compound notes
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