| Identification | More | [Name]
4-Hydroxy-2,6-dimethylpyridine | [CAS]
13603-44-6 | [Synonyms]
2,6-DIMETHYL-4-HYDROXYPYRIDINE
2,6-DIMETHYL-PYRIDIN-4-OL
4-HYDROXY-2,6-DIMETHYLPYRIDINE
4-PYRIDINOL, 2,6-DIMETHYL-
2,6-Dimethyl-4-hydroxypyridine 98%
2,6-Dimethyl-4-pyridinol
2,6-Dimethyl-4-hydroxypyridine ,98%
2,6-Dimethylpyridine-4-ol | [EINECS(EC#)]
237-089-2 | [Molecular Formula]
C7H9NO | [MDL Number]
MFCD00956021 | [Molecular Weight]
123.15 | [MOL File]
13603-44-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow to Brown Cryst | [Melting point ]
230-232°C | [Boiling point ]
351 °C | [density ]
1,053g/cm | [refractive index ]
1,501-1,503 | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly) | [form ]
Solid | [pka]
5.49±0.23(Predicted) | [color ]
White to Off-White | [Detection Methods]
HPLC | [InChI]
InChI=1S/C7H9NO/c1-5-3-7(9)4-6(2)8-5/h3-4H,1-2H3,(H,8,9) | [InChIKey]
PRAFLUMTYHBEHE-UHFFFAOYSA-N | [SMILES]
C1(C)=NC(C)=CC(O)=C1 | [LogP]
0.190 (est) | [CAS DataBase Reference]
13603-44-6(CAS DataBase Reference) |
| Safety Data | Back 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:Wear suitable protective clothing . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow to Brown Cryst | [Uses]
2,6-Dimethyl-4-hydroxypyridine is a useful synthetic intermediate. It is used in the synthesis of disubstituted pyridinyl-aminohydantoins as selective human BACE1 inhibitors. | [Synthesis]
The general procedure for the synthesis of 2,6-dimethyl-4-hydroxypyridine from dehydroacetic acid was as follows: five different batches of dehydroacetic acid (1.5 g, 8.92 mmol) were suspended in concentrated ammonia (4 mL) and placed in a microwave reactor (Discover system, 150 W, CEM Corporation, Matthews, North Carolina, USA) and microwave irradiated at 120°C for 20 min. Upon completion of the reaction, the reaction mixture was cooled and all batches were combined and subsequently evaporated to dryness to afford the target product 2,6-dimethyl-4-hydroxypyridine. The mass of the product was 5.91 g (108% yield), which was analyzed by LC/MS showing a purity of 73%. Unreacted dehydroacetic acid was present as a residual mass balance.The LC/MS retention time was 0.67 min and the mass spectrum (ES+) showed m/z 168 (M + CH3CN + H). | [References]
[1] Patent: WO2008/57497, 2008, A2. Location in patent: Page/Page column 252-253
[2] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 252-253
[3] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 252-253
[4] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 6, p. 373 - 377
[5] Chemische Berichte, 1887, vol. 20, p. 159 |
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