|
|
| | 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 | | EINECS: | | | Product Categories: | | | 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) |
| 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 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 |
|