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158063-66-2

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158063-66-2 Structure

158063-66-2 Structure
IdentificationMore
[Name]

4-(Trifluoromethyl)nicotinic acid
[CAS]

158063-66-2
[Synonyms]

4-(TRIFLUOROMETHYL)NICOTINIC ACID
4-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXYLIC ACID
BUTTPARK 43\57-42
RARECHEM AL BO 0760
4-(Trifluoromethyl)nicotinic acid 98%
4-(Trifluoromethyl)nicotinicacid98%
4-(Trifluromethyl)nicotinic acid
[EINECS(EC#)]

623-902-1
[Molecular Formula]

C7H4F3NO2
[MDL Number]

MFCD00082626
[Molecular Weight]

191.11
[MOL File]

158063-66-2.mol
Chemical PropertiesBack Directory
[Melting point ]

146-148 °C(lit.)
[Boiling point ]

290.4±40.0 °C(Predicted)
[density ]

1.484±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

2.50±0.36(Predicted)
[color ]

Pale Yellow to Dark Yellow
[InChI]

InChI=1S/C7H4F3NO2/c8-7(9,10)5-1-2-11-3-4(5)6(12)13/h1-3H,(H,12,13)
[InChIKey]

LMRJHNFECNKDKH-UHFFFAOYSA-N
[SMILES]

C1=NC=CC(C(F)(F)F)=C1C(O)=O
[CAS DataBase Reference]

158063-66-2(CAS DataBase Reference)
[EPA Substance Registry System]

3-Pyridinecarboxylic acid, 4-(trifluoromethyl)- (158063-66-2)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Methanol-->Tetrahydrofuran-->n-Butyllithium-->Nitrogen-->Carbon dioxide-->Diisopropylamine-->Ammonium formate-->Potassium fluoride-->Cuprous iodide-->N-Methyl-2-pyrrolidone-->(Trifluoromethyl)trimethylsilane-->PALLADIUM, 10% ON CHARCOAL-->2,6-Dichloro-4-trifluoromethyl-nicotinic acid-->2-Chloro-4-iodopyridine-->4-(Trifluoromethyl)nicotinamide-->3-Cyano-2,6-dihydroxy-4-(trifluoromethyl)pyridine-->4-(Trifluoromethyl)nicotinonitrile-->4-(Trifluoromethyl)pyridine
[Preparation Products]

3-Pyridinecarbonyl chloride, 4-(trifluoromethyl)- (9CI)
Hazard InformationBack Directory
[Uses]

4-(Trifluoromethyl)-3-Pyridinecarboxylic Acid is a useful synthetic intermediate. It can be used to prepare pyridine carboxamides as palm site inhibitors of HCV NS5B polymerase. It can also be used to synthesize pyrazolylcarboxanilides as Ca2+ release-activated Ca2+ (CRAC) channel inhibitors.
[Application]

4-(Trifluoromethyl)nicotinic acid is a trifluoromethyl-containing aromatic compound with unique biological activity, which can be used as a precursor material for the preparation of other pesticides or medicines. 4-(Trifluoromethyl)nicotinic acid is a key intermediate of flonicamid, a highly effective insecticide.
[Definition]

ChEBI: 4-(trifluoromethyl)nicotinic acid is a member of pyridines and an aromatic carboxylic acid.
[Preparation]

synthesis of 4-(Trifluoromethyl)nicotinic acid: add 5g (0.0192mol) Methyl 2,6-dichloro-4-(trifluoromethyl)nicotinate in turn to a 100mL three-necked flask, 0.3g of 10% Pd/C (water content 63.45%) ), 5.25g (0.0389mol) CH3COONa 3H2O and 20mL ethanol, after stirring and dissolving, nitrogen was replaced 3 times to discharge air, after hydrogen replacement 2 times, the reaction was stirred at room temperature for 8h under a hydrogen atmosphere until no hydrogen was absorbed to complete the reaction, and suction filtration was recovered. Palladium carbon, washed the filter cake 3 times with ethanol, the filtrate was rotary evaporated to remove the solvent, added 20 mL of water to the obtained solid, fully shaken to dissolve it, added hydrochloric acid to adjust pH=2～3, extracted 3 times with ethyl acetate, The organic phases were combined and washed three times with saturated brine, dried over anhydrous sodium sulfate, and rotary-evaporated to obtain 3.3 g of a pale yellow solid with a yield of 90.4%.
[Synthesis]

4-(TRIFLUOROMETHYL)NICOTINAMIDE

158062-71-6

4-(Trifluoromethyl)nicotinic acid

158063-66-2

General procedure for the synthesis of 4-(trifluoromethyl)nicotinic acid from 4-(trifluoromethyl)nicotinamide: 9.5 g of 4-(trifluoromethyl)nicotinamide, 1.5 g of Pd/MCM-22 catalyst, and 40 ml of a 25% aqueous sodium hydroxide solution were added to a 250-mL flask at room temperature. The reaction mixture was heated to 100 °C and kept reacting for 4 hours until the solid was completely dissolved to form a light yellow transparent solution. Upon completion of the reaction, the mixture was cooled to room temperature, the pH was adjusted to 2 with concentrated hydrochloric acid, stirred and diafiltrated. The residue was washed with water and dried to give 4-trifluoromethylnicotinic acid as a white powdery solid.

[References]

[1] Patent: CN108586328, 2018, A. Location in patent: Page/Page column 4-7
[2] Patent: EP1460071, 2004, A1. Location in patent: Page 40
Spectrum DetailBack Directory
[Spectrum Detail]

4-(Trifluoromethyl)nicotinic acid(158063-66-2)1HNMR
4-(Trifluoromethyl)nicotinic acid(158063-66-2)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

4-(trifluoromethyl)nicotinic acid(158063-66-2)
[Alfa Aesar]

4-(Trifluoromethyl)nicotinic acid, 98%(158063-66-2)
[Sigma Aldrich]

158063-66-2(sigmaaldrich)
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