4-Hydroxy-2,6-dimethylpyridine Chemical Properties

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

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39

HazardClass 

IRRITANT

HS Code 

29333990

4-Hydroxy-2,6-dimethylpyridine Usage And Synthesis

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

4-Hydroxy-2,6-dimethylpyridine(13603-44-6)Related Product Information

• 4-Hydroxy-2,6-dimethylpyridine
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• 5-Bromo-3-cyano-2-hydroxy-4,6-dimethylpyridine, 98%
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• 5,7-DIMETHYLPYRIDO[2,3-D]PYRIMIDIN-4(3H)-ONE
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• 2-Hydroxy-4,6-dimethylpyridine-3-carbonitrile ,98%,2-hydroxy-4,6-dimethylpyridine-3-carbonitrile,3-Cyano-2-hydroxy-4,6-dimethylpyridine, 98%
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• 4'-METHOXY-2,2':6',2''-TERPYRIDINE
• 4'-HYDROXY-2,2':6',2''-TERPYRIDINE
• COLLISMYCIN A
• 4-[2,6-BIS(TRIFLUOROMETHYL)PYRIDIN-4-YLOXY]ANILINE
• 5,8-DIHYDRO-4,6-DIHYDROXY-5,8-DIOXO-2-QUINOLINECARBOXYLIC ACID
• 4'-ETHOXY-2,2':6',2''-TERPYRIDINE