627098-02-6

Basic information

• Product Name: 3-Pyridinol,6-(dimethylamino)-2,4-dimethyl-(9CI)
• Synonyms: 3-Pyridinol,6-(dimethylamino)-2,4-dimethyl-(9CI)
• CAS NO: 627098-02-6
• Molecular Formula: C9H14N2O
• Molecular Weight: 166.22026
• Product Categories: AMINETERTIARY
• Mol File: 627098-02-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 132 °C
• Boiling Point: 370.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.096±0.06 g/cm3(Predicted)
• PKA: 12.14±0.10(Predicted)
• CAS DataBase Reference: 3-Pyridinol,6-(dimethylamino)-2,4-dimethyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinol,6-(dimethylamino)-2,4-dimethyl-(9CI)(627098-02-6)
• EPA Substance Registry System: 3-Pyridinol,6-(dimethylamino)-2,4-dimethyl-(9CI)(627098-02-6)

Safety Data

• Hazardous Substances Data: 627098-02-6(Hazardous Substances Data)

Upstream product

• 627098-10-6 5-bromo-4,6-dimethyl-2-(dimethylamino)pyridine 
• 5407-87-4 2-Amino-4,6-dimethylpyridine 
• 1083329-37-6 5-benzyloxy-4,6-dimethyl-2-N,N-dimethylaminopyridine 

Relevant articles and documents

6-amino-3-pyridinols: Towards diffusion-controlled chain-breaking antioxidants

The incorporation of nitrogen in the phenolic ring leads to compounds with very low phenolic O-H bond dissociation enthalpies, and thus high reactivities towards peroxyl radicals, but which are reasonably stable to direct reactions with air. The 3-pyridinols 1 and 2 are extremely effective peroxyl-radical-trapping chain-breaking antioxidants.

Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain-breaking antioxidants

The synthesis and study of a series of 6-substituted-2,4-dimethyl-3- pyridinols having interesting antioxidant properties is reported. The general synthetic strategy leading to the compounds involved a low-temperature aryl bromide-to-alcohol conversion as the last step. 2,4-Dimethyl-3-pyridinol (1a), 2,4,6-trimethyl-3-pyridinol (1b), and 2,4-dimethyl-6-(dimethylamino)-3-pyridinol (1d) were thus prepared from the corresponding 3-bromopyridine precursor. The methoxy derivative 2,4-dimethyl-6-(methoxy)-3-pyridinol (1c) was also prepared by an alternate route via a Baeyer-Villiger reaction on the substituted benzaldehyde precursor. Novel bicyclic pyridinols 2 and 3 required prior construction of the ring structure. Thus, 2 was prepared by the use of a 6-step intramolecular Friedel-Crafts strategy, and 3 required an 11-step sequence with a thermolytic intramolecular inverse-demand Diels-Alder reaction between a pyrimidine ring and an alkyne as the key step. Basicities of the pyridinols approached physiological pH with increasing electron density in the ring. Pyridinols 1a-d were found to be indefinitely stable to air oxidation while 2 and 3 decomposed upon extended exposure to the atmosphere. The reactivities of the pyridinols toward chain-carrying peroxyl radicals in homogeneous organic solution were examined by studying the kinetics of radical-initiated styrene autoxidations under controlled conditions. These experiments revealed that some of the newly synthesized pyridinols are the most effective phenolic chain-breaking antioxidants reported to date.