4-Nitro-2-picoline N-oxide Chemical Properties

Melting point:

155-159 °C(lit.)

Boiling point:

277.46°C (rough estimate)

Density 

1.4564 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO, Methanol

pka

-1.18±0.10(Predicted)

form 

powder

color 

yellow to light orange

λmax

333nm(EtOH)(lit.)

BRN 

135501

InChI

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

InChIKey

FTTIAVRPJGCXAC-UHFFFAOYSA-N

SMILES

C1(C)[N+]([O-])=CC=C([N+]([O-])=O)C=1

CAS DataBase Reference

5470-66-6(CAS DataBase Reference)

NIST Chemistry Reference

4-Nitro-2-picoline-n-oxide(5470-66-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

22-26-36

RIDADR 

2811

WGK Germany 

3

RTECS 

UT5710000

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:2-Methyl-4-nitropyridine 1-oxide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Nitro-2-picoline N-oxide Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

A nitroheterocyclic compound and its potential suitability as radiosensitizer for cancer radiotherapy.

Reactivity Profile

4-Nitro-2-picoline N-oxide could be used to synthesize 2-Methyl-4-nitro-6-(pyridin-2-yl)pyridine 1-oxide which is a key intermediate of Caerulomycin E and A[1].
 

Synthesis

General procedure for the synthesis of 2-methyl-4-nitropyridine-N-oxide from 2-methylpyridine-N-oxide: to a solution containing 2-methylpyridine-N-oxide (4 g, 36.0 mmol), concentrated sulfuric acid (10 mL) was slowly added in a sealed tube. The reaction mixture was stirred at 70°C for 16 hours. The completion of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was cooled to room temperature, quenched with ice-cold water (100 mL) and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was ground with a hexane solution of 10% ethyl acetate (50 mL) to give 2-methyl-4-nitropyridine-N-oxide as a yellow solid. Yield: 4 g (70%); 1H NMR (400 MHz, DMSO-d6): δ 8.41-8.45 (m, 2H), 8.06-8.10 (m, 1H), 2.42 (s, 3H).

References

[1] Zhang, Fang , and X. F. Duan . "Facile one-pot direct arylation and alkylation of nitropyridine N-oxides with Grignard reagents. " Organic Letters 43.13(2012).

4-Nitro-2-picoline N-oxide(5470-66-6)Related Product Information

• Methylparaben
• 2-Picoline
• 4-Nitropyridine N-oxide
• Pyridine-N-oxide
• 2,6-Lutidine
• 2-Chloro-5-chloromethylpyridine
• 4-Nitropyridine
• 4-Methylpyridine
• 2-Picoline-N-oxide
• 2-Methyl-4-nitropyridine
• 2,4,6-Collidine
• METHYL THIOPHENE-2-CARBOXYLATE
• Methyl acrylate
• Kresoxim-methyl
• Bensulfuron methyl
• Methyl acetate
• Thiophanate-methyl
• Methyl