2-(Trifluoromethyl)pyridin-4-ol Chemical Properties

Melting point:

120.0 to 124.0 °C

Boiling point:

324.4±37.0 °C(Predicted)

Density 

1.423

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

7.53±0.10(Predicted)

form 

Powder

color 

Off-white

InChI

InChI=1S/C6H4F3NO/c7-6(8,9)5-3-4(11)1-2-10-5/h1-3H,(H,10,11)

InChIKey

LKHCWMQMRXAPHX-UHFFFAOYSA-N

SMILES

C1(C(F)(F)F)=NC=CC(O)=C1

Safety Information

HS Code 

2933399990

2-(Trifluoromethyl)pyridin-4-ol Usage And Synthesis

Uses

2-(Trifluoromethyl)pyridin-4-ol is a pyridine derivative. Its molecular structure contains trifluoromethyl and hydroxyl reactive groups, which have high reactivity and are prone to substitution reactions, and can be used to prepare 4-Chloro-2-(trifluoromethyl)pyridine, 2-(trifluoromethyl)isonicotinic acid and 4-Amino-2-( trifluoromethyl)pyridine.

Synthesis

Step F4: Under dry conditions, 3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid (0.092 g, 0.302 mmol) and 1-(3-methylcyclopentyl)-2-piperazinone (0.060 g, 0.274 mmol) were dissolved in DMF (3.07 mL). Subsequently, HATU (0.115 g, 0.302 mmol) and DIPEA (0.120 mL, 0.686 mmol) were added. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with EtOAc and water. The organic phase was separated and washed sequentially with 5% LiCl aqueous solution (3 times), saturated NaHCO3 aqueous solution (3/4 v/v), brine, then dried with anhydrous MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (elution gradient: 0-2% MeOH/DCM) to afford the title compound (0.101 g, 79% yield) as a white solid.1H NMR (400 MHz, chloroform-d) δ ppm: 7.37-7.48 (m, 1H), 7.06 (br.s., 1H), 4.87-5.21 (m, 1H) , 4.42-4.51 (m, 1H), 4.34 (s, 1H), 3.90-4.12 (m, 2H), 3.43 (d, J = 5.66 Hz, 2H), 1.79-2.19 (m, 5H), 1.46-1.56 (m, 1H), 1.10-1.32 (m, 4H), 1.04 (ddd, J = 12.58, 6.44, 2.24 H 6.44, 2.24 Hz, 3H), 0.87 (d, J = 5.27 Hz, 2H). ES-LCMS m/z: 469.3 (M + 1).

References

[1] Patent: WO2011/50284, 2011, A1. Location in patent: Page/Page column 127

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