2-CHLORO-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE Chemical Properties

Boiling point:

249℃

Density 

1.618

Flash point:

105℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

-6.04±0.10(Predicted)

Appearance

Light yellow to yellow Liquid

InChI

InChI=1S/C6H2ClF3N2O2/c7-5-4(6(8,9)10)1-3(2-11-5)12(13)14/h1-2H

InChIKey

OPEZLLCPUDLUFV-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C([N+]([O-])=O)C=C1C(F)(F)F

Safety Information

RIDADR 

2810

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933399990

2-CHLORO-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-chloro-3-trifluoromethyl-5-nitropyridine from 2-hydroxy-5-nitro-3-trifluoromethylpyridine: Thionyl chloride (SOCl2, 18.45 mL, 253 mmol) was slowly added dropwise to a reaction vial containing 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2.63 g, 12.64 mmol). Subsequently, N,N-dimethylformamide (DMF, 1.957 mL, 25.3 mmol) was added as a catalyst. The reaction mixture was stirred at 100°C for 10 hours. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure to remove excess thionyl chloride. The concentrated residue was extracted by partitioning between ethyl acetate (EA) and saturated sodium bicarbonate (NaHCO3) solution. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the crude product 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (2.46 g, 10.86 mmol, 86% yield), which could be used in the next reaction without further purification. Thin layer chromatography (TLC) analysis conditions: petroleum ether/ethyl acetate (PE/EA = 5:1), Rf = 0.6. 1H NMR (400 MHz, CDCl3) δ: 9.23-9.59 (m, 1H), 8.79 (d, J = 2.4 Hz, 1H).

References

[1] Patent: US2014/275111, 2014, A1. Location in patent: Paragraph 0259; 0260
[2] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 49; 59; 63; 87; 88; 124
[3] Patent: US2007/60623, 2007, A1. Location in patent: Page/Page column 39
[4] Patent: WO2016/37578, 2016, A1. Location in patent: Page/Page column 84
[5] Patent: WO2006/42289, 2006, A2. Location in patent: Page/Page column 52