ChemicalBook--->CAS DataBase List--->158062-71-6

158062-71-6

158062-71-6 Structure

158062-71-6 Structure
IdentificationMore
[Name]

4-(TRIFLUOROMETHYL)NICOTINAMIDE
[CAS]

158062-71-6
[Synonyms]

4-(TRIFLUOROMETHYL)NICOTINAMIDE
4-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXAMIDE
Trifluoromethylpyridinecarboxamide2
[Molecular Formula]

C7H5F3N2O
[MDL Number]

MFCD00126658
[Molecular Weight]

190.12
[MOL File]

158062-71-6.mol
Chemical PropertiesBack Directory
[Melting point ]

165°C
[Boiling point ]

292.0±40.0 °C(Predicted)
[density ]

1.409±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,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 DataBack Directory
[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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

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

2-Propenenitrile, 3-[(4,4,4-trifluoro-3-oxo-1-buten-1-yl)amino]-, (2Z)-

533932-97-7

2-Propenenitrile, 3-[(4,4,4-trifluoro-3-oxo-1-buten-1-yl)amino]-, (2E)-

533932-96-6

4-(TRIFLUOROMETHYL)NICOTINAMIDE

158062-71-6

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
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