3-Methylpicolinonitrile Chemical Properties

Melting point:

83-87 °C(lit.)

Boiling point:

141°C 38mm

Density 

1.1151 (rough estimate)

refractive index 

1.5500 (estimate)

Flash point:

115°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-0.03±0.10(Predicted)

form 

Crystalline Powder

color 

Light beige

BRN 

112001

CAS DataBase Reference

20970-75-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37

RIDADR 

3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333999

MSDS

• Language:English Provider:3-Methylpyridine-2-carbonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Methylpicolinonitrile Usage And Synthesis

Chemical Properties

light beige crystalline powder

Uses

3-Methylpicolinonitrile is a useful chemical reagent. It has been used in the synthesis of, triazolo[1,5-c]pyrimidines as potential antiasthma agents; ?s-tetrazine derivatives as anti-tumor agents.

Synthesis

II-1-1: Synthesis of 2-cyano-3-methylpyridine 10.9 g (0.1 mol) of 3-methylpyridine-N-oxide was mixed with 12.6 g (0.1 mol) of dimethyl sulfate and the reaction was stirred at 70-75°C for 2 hours. Subsequently, a solution prepared from 13.0 g (0.2 mol) potassium cyanide dissolved in 10-40 mL of water was slowly added dropwise to the reaction system while maintaining stirring. After the dropwise addition was completed, the reaction mixture was continued to be stirred at the same temperature for 1 hour and then at room temperature for another 1 hour. Upon completion of the reaction, it was diluted with 150 mL of water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent ratio: ethyl acetate/hexane = 2:8 to 3:7, 2:8 for the second time), and finally recrystallized from hexane to give 2.20 g of colorless solid product in 18.6% yield. The melting point of the product was 82.5-83.5 °C. IR (KBr, cm-1): 2210, 1560.

References

[1] Patent: US5219847, 1993, A
[2] Chemical and Pharmaceutical Bulletin, 1959, vol. 7, p. 925,928

3-Methylpicolinonitrile(20970-75-6)Related Product Information

• 4-Methylpyridine
• 2,4,6-Collidine
• 2,6-Lutidine
• 3-Picoline
• Azamethiphos
• Trimethylsilyl cyanide
• 2-Cyanopyridine
• 2-CYANOPYRIDINE-3-CARBOXYLIC ACID
• 3-CYANO-5-METHYLPYRIDINE
• 3-[2-(3-Chlorophenyl)ethyl]-2-pyridinecarbonitrile
• 5-hydroxy-3-methylpicolinonitrile
• 5-Methylpicolinonitrile
• 2-Chloro-4-methylpyridine-3-carbonitrile
• 2-Chloro-6-methyl-3-pyridinecarbonitrile
• 3-Cyano-2-methylpyridine
• 3-Cyano-2,6-dihydroxy-4-methylpyridine
• 5-CYANO-2-METHYLPYRIDINE
• 4-Methylpicolinonitrile