4-(TRIFLUOROMETHYL)NICOTINAMIDE CAS 158062-71-6

Introduction：Basic information about 4-(TRIFLUOROMETHYL)NICOTINAMIDE CAS 158062-71-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

4-(TRIFLUOROMETHYL)NICOTINAMIDE Basic information

• Product Name: 4-(TRIFLUOROMETHYL)NICOTINAMIDE
• Synonyms: 4-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXAMIDE;4-(TRIFLUOROMETHYL)NICOTINAMIDE;Trifluoromethylpyridinecarboxamide2;4-trifluoroMethyl-3-pyridinecarboxaMide;FlonicaMide Metabolite (TFNA-AM type,4-TriuoroMethylnicotin aMide);3-Pyridinecarboxamide, 4-(trifluoromethyl)-;TFNA-AM;TFNA-AM Standard
• CAS: 158062-71-6
• MF: C7H5F3N2O
• MW: 190.12
• Mol File: 158062-71-6.mol

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

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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

4-(TRIFLUOROMETHYL)NICOTINAMIDE Preparation Products And Raw materials

• Raw materials: 2-Propenenitrile, 3-[(4,4,4-trifluoro-3-oxo-1-buten-1-yl)amino]-, (2Z)--->2-Propenenitrile, 3-[(4,4,4-trifluoro-3-oxo-1-buten-1-yl)amino]-, (2E)--->2,6-DICHLORO-4-(TRIFLUOROMETHYL)NICOTINAMIDE-->Methanol-->2,6-Dichloro-4-(trifluoromethyl)nicotinonitrile-->Sodium hydroxide-->3-CYANO-2,6-DIHYDROXY-4-(TRIFLUOROMETHYL)PYRIDINE-->4-(Trifluoromethyl)nicotinonitrile
• Preparation Products: 4-(Trifluoromethyl)nicotinic acid