3-Cyano-4-methylpyridine Chemical Properties

Melting point:

41-44°C

Boiling point:

108-111°C 20mm

Density 

1.08±0.1 g/cm3(Predicted)

Flash point:

108-111°C/20mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.45±0.18(Predicted)

color 

White to Orange to Green

BRN 

112016

InChI

InChI=1S/C7H6N2/c1-6-2-3-9-5-7(6)4-8/h2-3,5H,1H3

InChIKey

XLAPHZHNODDMDD-UHFFFAOYSA-N

SMILES

C1=NC=CC(C)=C1C#N

CAS DataBase Reference

5444-01-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

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

Safety Statements 

22-36/37/39-36-26-36/37

RIDADR 

3439

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

3-Cyano-4-methylpyridine Usage And Synthesis

Uses

3-Cyano-4-methylpyridine, is an intermediate for the synthesis of various pharmaceutical compounds, including inhibitors and anticancer agents. It can be used for the preparation of a series of azaindenoisoquinoline topoisomerase I I inhibitors and potential anticancer agents.

Synthesis

General procedure for the synthesis of 3-cyano-4-methylpyridine (112) from 3-cyano-4-methyl-2,6-dichloropyridine (Ref. J. Org. Chem. 1960, 25, 560-564): palladium dichloride (50 mg, 0.3 mmol) was added to a degassed 3-cyano-4-methyl-2,6-dichloropyridine (5.0 g, 27 mmol) and sodium acetate (4.5 g, 55 mmol) in a methanol (100 mL) solution. The reaction mixture was stirred under hydrogen (1 atm) atmosphere for 14 hours at room temperature. After completion of the reaction, the precipitate was filtered and washed with methanol (3 x 20 mL). The filtrates were combined, the solvent was removed by evaporation under reduced pressure and chloroform (50 mL) was added to the residue. The chloroform solution was filtered through a thin silica gel pad and the silica gel pad was washed with additional chloroform. The filtrate was evaporated to dryness to afford 3-cyano-4-methylpyridine (112) (2.9 g, 93% yield) as a yellow oil. The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 8.77 (s, 1H), 8.63 (s, J = 6.0 Hz, 1H), 7.3 (d, J = 6.0 Hz, 1H), 2.56 (s, 3H). The resulting 3-cyano-4-methylpyridine (112) can be used in subsequent reactions without further purification.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1682 - 1697
[2] Patent: US2014/18360, 2014, A1. Location in patent: Paragraph 0146
[3] Patent: EP1348706, 2003, A1. Location in patent: Page/Page column 36
[4] Letters in Organic Chemistry, 2016, vol. 13, # 6, p. 450 - 452

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