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

Melting point:

189 °C

Boiling point:

276.2±40.0 °C(Predicted)

Density 

1.61±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

5.89±0.10(Predicted)

form 

Solid

color 

Off-white

InChI

InChI=1S/C6H3F3N2O3/c7-6(8,9)3-1-4(11(13)14)5(12)10-2-3/h1-2H,(H,10,12)

InChIKey

JYXKHKBZLLIWEV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

33252-64-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-26-36/37/39

RIDADR 

NA3077

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

2933399990

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

Synthesis

The general procedure for the synthesis of 2-hydroxy-3-nitro-5-trifluoromethylpyridine using 2-hydroxy-5-trifluoromethylpyridine as starting material was as follows: 2-hydroxy-5-trifluoromethylpyridine (10.0 g, 61.3 mmol) was dissolved in concentrated sulfuric acid (50 mL), and the reaction system was cooled to 0 °C. Fuming nitric acid (14 mL, 92 mmol) was slowly added dropwise at 0 °C. After the dropwise addition, the reaction was kept at 0 °C and continued to be stirred for 1 h. Subsequently, the temperature of the reaction was raised to 65 °C and the reaction was continued to be stirred for 24 h. The reaction temperature was increased to 65 °C and the reaction was continued to be stirred. After completion of the reaction, the reaction system was cooled to room temperature and the reaction was quenched by slowly pouring into ice (300 g). Subsequently, 50% aqueous sodium hydroxide solution (85 mL) was slowly added to neutralize the reaction mixture. The aqueous phase was extracted several times with ethyl acetate (4 x 200 mL), all organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a yellow solid 2-hydroxy-3-nitro-5-trifluoromethylpyridine 7.4 g in 58% yield. The product was characterized by 1H NMR (CDCl3): δ 8.66 (s, 1H), 8.29 (s, 1H).

References

[1] Patent: WO2009/7418, 2009, A1. Location in patent: Page/Page column 23
[2] Patent: CN105111209, 2017, B. Location in patent: Paragraph 0029; 0036
[3] Patent: US2006/4018, 2006, A1. Location in patent: Page/Page column 14; 35
[4] Patent: WO2011/43404, 2011, A1. Location in patent: Page/Page column 111-112
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987

2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE(33252-64-1)Related Product Information

• 2-(4-BROMOPHENYL)PROPAN-2-OL
• 5-AMINOMETHYL-1H-PYRIDIN-2-ONE
• 2-HYDROXY-3-PHENYLPYRIDINE
• 5-IODO-3-(TRIFLUOROMETHYL)-2(1H)-PYRIDINONE
• 5-BROMO-3-CHLORO-2-HYDROXYPYRIDINE
• 3-BroMo-6-chloropyridin-2-ol
• 2-HYDROXY-5-METHYLPYRAZINE
• 6-CHLORO-1,3-DIHYDRO-2H-IMIDAZO[4,5-B]PYRIDIN-2-ONE
• 2-HYDROXY-5-IODO-BENZONITRILE
• 3-Cyano-2-hydroxy-5-iodopyridine
• 2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE,2-Hydroxy-5-nitro-3-(trifluoromethyl)pyridine 98%,2-Hydroxy-5-nitro-3-(trifluoromethyl)pyridine98%
• 5-Trifluoromethyl-pyridin-3-ylamine
• 3-METHYL-5-NITROPYRIDINE
• 2-Hydroxy-5-methyl-3-nitropyridine
• 2-HYDROXY-3-NITROPYRIDINE
• 5-Methylpyridin-3-amine
• 2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE
• 2-HYDROXY-3-AMINO-5-PICOLINE