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2-(Trifluoromethyl)pyridine

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2-(Trifluoromethyl)pyridine Basic information
Product Name:2-(Trifluoromethyl)pyridine
Synonyms:Pyridine, 2-(trifluoromethyl)-;ALPHA,ALPHA,ALPHA-TRIFLUORO-2-PICOLINE;à,à,à-trifluoro-2-picoline;α,α,α-trifluoro-2-picoline;2-(TRIFLUOROMETHYL)PYRIDINE;2-(Trifluoromethyl)pyridine,α,α,α-Trifluoro-2-picoline;2-trifluoromethylpyridine UNDRE RD;2-(CF3)-Pyridine
CAS:368-48-9
MF:C6H4F3N
MW:147.1
EINECS:626-032-0
Product Categories:Fluorine series;pharmacetical;Pyridines;Pyridine
Mol File:368-48-9.mol
2-(Trifluoromethyl)pyridine Structure
2-(Trifluoromethyl)pyridine Chemical Properties
Boiling point 139-141 °C
density 1.275 g/mL at 25 °C
refractive index n20/D 1.419
Fp 109 °F
storage temp. Inert atmosphere,Room Temperature
solubility Soluble in most organic solvents.
pka0.60±0.12(Predicted)
form clear liquid
color Colorless to Light yellow
BRN 3112
InChIInChI=1S/C6H4F3N/c7-6(8,9)5-3-1-2-4-10-5/h1-4H
InChIKeyATRQECRSCHYSNP-UHFFFAOYSA-N
SMILESC1(C(F)(F)F)=NC=CC=C1
CAS DataBase Reference368-48-9(CAS DataBase Reference)
NIST Chemistry Reference2-(CF3)-pyridine(368-48-9)
Safety Information
Hazard Codes Xi,F
Risk Statements 10-36/37/38
Safety Statements 16-26-36
RIDADR UN 1993 3/PG 3
WGK Germany 3
Hazard Note Flammable/Irritant
HazardClass 3
PackingGroup III
HS Code 2933399990
Storage Class3 - Flammable liquids
Hazard ClassificationsEye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
2-(Trifluoromethyl)pyridine English
SigmaAldrich English
ALFA English
2-(Trifluoromethyl)pyridine Usage And Synthesis
UsesLithiation with n-BuLi/LiOCH2CH2NMe2?takes place at the 6-position, affording access to 6-substituted derivatives. With LiTMP?. It is a building block in heterocycle synthesis.
Synthesis Reference(s)Synthesis, p. 932, 1980 DOI: 10.1055/s-1980-29276
Synthesis
2-Bromopyridine

109-04-6

(Trifluoromethyl)trimethylsilane

81290-20-2

2-(Trifluoromethyl)pyridine

368-48-9

AgF (1.27 g, 10 mmol) was dissolved in 10 mL of DMF at room temperature and stirred thoroughly. Subsequently, Me3SiCF3 (1.7 g, 12 mmol) was added to the mixture and stirring was continued for 20 minutes. Next, copper powder (1.0 g, 15 mmol) was added and the reaction mixture was stirred for 4 hours to ensure complete formation of CuCF3. Then, the corresponding halogenated compound (9 mmol, 4.5 mmol for 2,6-dibromopyridine) was added and the reaction mixture continued to be stirred under the conditions listed in Table 1. The progress of the reaction was monitored by 19F NMR spectroscopy until the signal of CuCF3 completely disappeared and the reaction was terminated. Upon completion of the reaction, the mixture was filtered to remove the solid precipitate and the filtrate was poured into 50 mL of water. The organic layer in the aqueous phase was extracted with ether and the extract was dried with MgSO4. Finally, the ether was removed by evaporation and the residue was purified by distillation under reduced pressure or crystallization to give the target product 2-trifluoromethylpyridine.

References[1] Journal of Fluorine Chemistry, 2012, vol. 133, p. 67 - 71
Tag:2-(Trifluoromethyl)pyridine(368-48-9) Related Product Information
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