2-Picoline-N-oxide Chemical Properties

Melting point:

41-45 °C(lit.)

Boiling point:

259-261 °C

Density 

1.1143 (rough estimate)

refractive index 

1.5444 (estimate)

Flash point:

>230 °F

storage temp. 

RT, stored under nitrogen

pka

pK1:1.029(+1) (25°C)

form 

powder to lump to clear liquid

color 

White or Colorless to Light yellow

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

106916

InChI

InChI=1S/C6H7NO/c1-6-4-2-3-5-7(6)8/h2-5H,1H3

InChIKey

CFZKDDTWZYUZKS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

931-19-1(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 2-methyl-, 1-oxide(931-19-1)

EPA Substance Registry System

2-Methylpyridine-1-oxide (931-19-1)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

36/37/38-20/21/22-10

Safety Statements 

26-36-24/25-16

WGK Germany 

3

F 

3

TSCA 

TSCA listed

HS Code 

29333990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:2-Picoline-N-oxide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Picoline-N-oxide Usage And Synthesis

Chemical Properties

light yellow to brown crystalline low melting mass

Uses

2-Picoline N-oxide is used in proteomics research. Also used as pharmaceutical intermediates.

Application

2-Methylpyridine 1-oxide is a useful building block for organic synthesis.

Definition

ChEBI: Picoline N-oxide is a member of methylpyridines and a member of pyridine N-oxides.

Synthesis

K2CO3 (20 mmol) and urea peroxide (10 mmol) were dissolved in dry 1,4-dioxane (100 mL), which was then stirred and reacted at room temperature for 1 hour. Trifluoroacetic anhydride (10 mmol) was added dropwise to the mixture below 12 ??C to bring the mixture back to room temperature. To the reaction mixture was added the corresponding 2-methylpyridine (1 mmol) and the mixture was stirred at 50 ??C overnight. The 1,4-dioxane was removed by distillation and replaced with dichloromethane, the mixture was washed with water (50 mL) and the resulting organic layer was dried over anhydrous MgSO4, filtered to remove the desiccant and the resulting filtrate was concentrated under vacuum to remove the solvent to give the 2-methylpyridine oxide.

Purification Methods

Purify the N-oxide by fractional distillation, and it can be recrystallised from *C6H6/hexane but is hygroscopic. [Bullitt & Maynard J Am Chem Soc 76 1370 1954, Ross et al. J Am Chem Soc 78 3625 1956, IR: Wiley & SlaymAker J Am Chem Soc 79 2233 1957.] The picrate has m 125-126.5o (from EtOH) [Boekelheide & Linn J Am Chem Soc 76 1286 1954]. The phthalate has m 115-116o (from EtOH) [den Hertog et al. Recl Trav Chim Pays-Bas 70 591 1951.]. [Beilstein 20 III/IV 2689, 20/5 V 479.]

2-Picoline-N-oxide(931-19-1)Related Product Information

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