3-HYDROXY-6-METHYL-2-NITROPYRIDINE Chemical Properties

Melting point:

106-107 °C (lit.)

Boiling point:

277.46°C (rough estimate)

Density 

1.4564 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

1.01±0.22(Predicted)

color 

Light orange to Yellow to Green

BRN 

974751

InChI

InChI=1S/C6H6N2O3/c1-4-2-3-5(9)6(7-4)8(10)11/h2-3,9H,1H3

InChIKey

WZMGQHIBXUAYGS-UHFFFAOYSA-N

SMILES

C1([N+]([O-])=O)=NC(C)=CC=C1O

CAS DataBase Reference

15128-90-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-HYDROXY-6-METHYL-2-NITROPYRIDINE Usage And Synthesis

Chemical Properties

yellow fine crystalline powder

Uses

3-Hydroxy-6-methyl-2-nitropyridine was used in the synthesis of 3-methoxy-6-methyl-2-nitropyridine.Molecular structure and corresponding vibrational assignments of 3-hydroxy-6-methyl-2-nitropyridine have been investigated using density functional theory (DFT).

General Description

Molecular structure and corresponding vibrational assignments of 3-hydroxy-6-methyl-2-nitropyridine have been investigated using density functional theory (DFT).

Synthesis

General procedure for the synthesis of 3-hydroxy-6-methyl-2-nitropyridine from 3-hydroxy-6-methylpyridine: 3-hydroxy-6-methylpyridine (23.6 g, 216 mmol) was dissolved in concentrated sulfuric acid (50 mL) and cooled to 0 °C. Fuming nitric acid (50 mL) was added slowly over a period of 1 hour. The reaction mixture was stirred at room temperature for 1 hour and then poured into ice (400 g) and the precipitate was collected by filtration. The resulting solid was dissolved in ethyl acetate and the organic layer was washed with brine (100 mL). The organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give 12.1 g of the title compound (36.3% yield). The melting point of the product was 102-105 °C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.44 (s, 3H), 7.52 (d, J = 8.5 Hz, 1H), 7.58 (d, J = 8.5 Hz, 1H). Mass spectrum (ESI-Q1MS) m/e 153 (M-H)+. Elemental analysis calculated values (C6H6N3O3): C, 46.76; H, 3.92; N, 18.18. Measured values: C, 46.65; H, 3.98; N, 18.10.

References

[1] Heterocycles, 1994, vol. 38, # 3, p. 529 - 540
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 11, p. 2031 - 2046
[3] Patent: US6133253, 2000, A
[4] Patent: US5155116, 1992, A
[5] Patent: US5084456, 1992, A

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