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6-METHYLNICOTINAMIDE

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CAS:6960-22-1
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  • Purity: 99.46%
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6-METHYLNICOTINAMIDE Basic information
Product Name:6-METHYLNICOTINAMIDE
Synonyms:6-METHYLPYRIDINE-3-CARBOXAMIDE;6-METHYLNICOTINAMIDE;5-CARBOXAMIDO-2-PICOLINE;6-Methylnicotinamide,98%;3-Pyridinecarboxamide, 6-methyl-;3-Pyridinecarboxamide,6-methyl-(9CI);6-METHYLPYRIDINE-3-CARBOXAMIDE (6-METHYLNICOTINAMIDE);Nicotinamide, 6-methyl-
CAS:6960-22-1
MF:C7H8N2O
MW:136.15
EINECS:204-624-6
Product Categories:AMIDE;Pyridines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Nicotine Derivatives;Pharmaceuticals;Heterocyclic Compounds;C7 and C8;Heterocyclic Building Blocks
Mol File:6960-22-1.mol
6-METHYLNICOTINAMIDE Structure
6-METHYLNICOTINAMIDE Chemical Properties
Melting point 197-199 °C(lit.)
Boiling point 289.4±28.0 °C(Predicted)
density 1.157±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility water: soluble50mg/mL, clear to slightly hazy, colorless to light yellow
form Solid
pka15.04±0.50(Predicted)
color Plae Beige to Pale Orange
Water Solubility water: soluble 50mg/mL, clear to slightly hazy, colorless to light yellow
BRN 112050
InChI1S/C7H8N2O/c1-5-2-3-6(4-9-5)7(8)10/h2-4H,1H3,(H2,8,10)
InChIKeyIJXDURUAYOKSIS-UHFFFAOYSA-N
SMILESCc1ccc(cn1)C(N)=O
CAS DataBase Reference6960-22-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HS Code 29333990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
6-METHYLNICOTINAMIDE Usage And Synthesis
Chemical PropertiesWhite soild
UsesA nicotinamide derivative that inhibits state 3 respiration in isolated rat liver mitochondria. It is toxic to rat B65 neuroblastoma cells and is used in studies associated with early symptoms of Parkinson''s disease.
Uses6-Methylpyridine-3-carboxamide may be used in chemical synthesis studies.
Uses6-Methylnicotinamide is a nicotinamide derivative that inhibits state 3 respiration in isolated rat liver mitochondria. It is toxic to rat B65 neuroblastoma cells and is used in studies associated with early symptoms of Parkinson's disease.
Synthesis
6-Methylnicotinic acid

3222-47-7

6-METHYLNICOTINAMIDE

6960-22-1

To a stirred dichloromethane (DCM) solution of 6-methylpyridine-3-carboxylic acid (0.3 g, 2 mmol) was added ammonium chloride (0.7 g, 13 mmol), triethylamine (TEA, 2.7 mL, 19 mmol), and propylphosphoric anhydride (T3P, 4 mL, 6.5 mmol) sequentially at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated sodium bicarbonate (NaHCO3) solution and the reaction mixture was extracted with dichloromethane (DCM). The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by Combiflash rapid chromatography system using 10% methanol (MeOH) in dichloromethane (DCM) solution as eluent to give white solid 6-methylnicotinamide (0.1 g, 33.6% yield). The product was confirmed by 1H NMR (DMSO-d6, 400 MHz): δ2.48 (s, 3H), 7.30 (d, J=8Hz, 1H), 7.44 (bs, 1H), 8.02 (bs, 1H), 8.07 (dd, J=2.4 Hz, J=2.4 Hz, 1H), 8.88 (s, 1H); mass spectra (ESI) m/z 137.1 ([M+H]+); HPLC analysis showed a purity of 98.97% at 264 nm.

References[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 5, p. 922 - 925
[2] Journal of Chemical Research, Miniprint, 1987, # 9, p. 2360 - 2384
Tag:6-METHYLNICOTINAMIDE(6960-22-1) Related Product Information
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