4-(TRIFLUOROMETHYL)NICOTINAMIDE Chemical Properties

Melting point:

165°C

Boiling point:

292.0±40.0 °C(Predicted)

Density 

1.409±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

14.29±0.50(Predicted)

color 

White to Off-White

InChI

InChI=1S/C7H5F3N2O/c8-7(9,10)5-1-2-12-3-4(5)6(11)13/h1-3H,(H2,11,13)

InChIKey

JUIWZYBJXUPIKF-UHFFFAOYSA-N

SMILES

C1=NC=CC(C(F)(F)F)=C1C(N)=O

CAS DataBase Reference

158062-71-6(CAS DataBase Reference)

EPA Substance Registry System

3-Pyridinecarboxamide, 4-(trifluoromethyl)- (158062-71-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933399990

4-(TRIFLUOROMETHYL)NICOTINAMIDE Usage And Synthesis

Uses

4-(Trifluoromethyl)nicotinamide (TFNA-AM) is a metabolite of Flonicamid (F405710); a novel insecticide with rapid inhibitory effect against aphid feeding.

Synthesis

Sodium hydroxide (600 mg, 15 mmol) was added as 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (mixture of IIa and IIb, 1.90 g, 10 mmol) and methanol (15 mL). The reaction mixture was heated to reflux for 6 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with hexane/acetone (1:1, v/v) as eluent to afford 4-(trifluoromethyl)nicotinamide (1.25 g, 65.6% yield). The product was characterized by 1H-NMR (200 MHz, DMSO-d6): δ 8.89 (1H, d, J = 5.1 Hz), 8.82 (1H, s), 8.18 (1H, brs), 7.85 (1H, brs), 7.81 (1H, d, J = 5.1 Hz).

References

[1] Patent: EP1460071, 2004, A1. Location in patent: Page 39
[2] Patent: EP1460071, 2004, A1. Location in patent: Page 40
[3] Patent: EP1460071, 2004, A1. Location in patent: Page 40

4-(TRIFLUOROMETHYL)NICOTINAMIDE(158062-71-6)Related Product Information

• 4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 4-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE
• 2,6-DICHLORO-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 2-METHOXY-4-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXAMIDE
• 2-METHOXY-4-(TRIFLUOROMETHYL)PYRIDINE-5-CARBOXAMIDE
• 2-CHLORO-5-NITRO-6-(3-NITROPHENYL)-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• N3-(2,4-DICHLOROBENZYL)-N3-PROPYL-6-CHLORO-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 2-CHLORO-N-(2,4-DICHLOROBENZYL)-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 6-CHLORO-N-[2-(3-CHLOROPHENYL)-2-OXOETHYL]-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 2-CHLORO-N-(2,4-DICHLORO-6-METHYLBENZYL)-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 2-CHLORO-6-(2-THIENYL)-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 6-CHLORO-N-(2,4-DICHLORO-6-METHYLBENZYL)-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• N-[[[(2,6-DIMETHOXYBENZYL)AMINO]CARBONYL]METHYL]-4-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXAMIDE
• 6-CHLORO-N'-(3-CHLOROBENZOYL)-4-(TRIFLUOROMETHYL)NICOTINOHYDRAZIDE
• N3-[2-(4-CHLOROPHENYL)-2-OXOETHYL]-6-CHLORO-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• N3-(2,4-DIFLUOROPHENYL)-2-CHLORO-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• 6-CHLORO-N-(4-METHOXYBENZYL)-4-(TRIFLUOROMETHYL)NICOTINAMIDE
• N-ETHYL-N-PHENYL-4-(TRIFLUOROMETHYL)NICOTINAMIDE