5-CYANO-2-METHYLPYRIDINE Chemical Properties

Melting point:

83-85°C

Boiling point:

216-217°C

Density 

1.08±0.1 g/cm3(Predicted)

Flash point:

216-217°C

storage temp. 

2-8°C

pka

2.51±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow

BRN 

111235

InChIKey

PBLOYQAQGYUPCM-UHFFFAOYSA-N

CAS DataBase Reference

3222-48-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

T+,T

Risk Statements 

22-41-25

Safety Statements 

26-36/37/39-45-39

RIDADR 

3439

WGK Germany 

1

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

5-CYANO-2-METHYLPYRIDINE Usage And Synthesis

Uses

5-Cyano-2-methylpyridine is used to synthesize acridone-based inhibitors of inosine 5'-monophosphate dehydrogenase (IMPDH). It is also used in the preparation of potent and selective nonpeptidic inhibitors of procollagen C-proteinase.This compound is suitable for pyruvate dehydrogenase (PDH) related research.

Synthesis

General procedure for the synthesis of 5-cyano-2-methylpyridine from 2-bromo-6-methylnicotinonitrile: a generalized method using Pd(OAc)2-PPh3, Pd2(dba)3-tbpf, Pd2(dba)3-DavePhos, Pd2(dba)3-P(t-Bu)3, Pd2(dba)3-XantPhos or Pd (OAc)2-XPhos as catalyst systems. First, anhydrous THF (13.2 mL) was degassed by bubbling argon for a few minutes, followed by the addition of Pd(OAc)2 (7.2 mg, 0.033 mmol, 5 mol%) and PPh3 (17.7 mg, 0.132 mmol, 20 mol%) and stirring of the resulting mixture for 30 minutes at room temperature. Next, halogenated heterocycles (0.66 mmol), TMEDA (0.130 g, 1.12 mmol, 1.7 eq.) and NaBH4 (42.4 mg, 1.12 mmol, 1.7 eq.) were added sequentially. The reaction mixture was stirred at room temperature or heated under argon protection at 65 °C for an appropriate time. After completion of the reaction, the residue was dissolved in brine and extracted with ethyl acetate. The organic phase was separated, dried and the solvent was evaporated, and finally the residue was purified by fast chromatography (using a mixture of petroleum ether and ethyl acetate) to give the pure hydrodehalogenated heterocyclic product.

References

[1] Tetrahedron Letters, 2010, vol. 51, # 12, p. 1562 - 1565
[2] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209

5-CYANO-2-METHYLPYRIDINE(3222-48-8)Related Product Information

• Ethyl 2-chloro-3-cyano-6-methylpyridine-4-,ETHYL 2-CHLORO-3-CYANO-6-METHYLPYRIDINE-4-CARBOXYLATE
• 3-CYANO-4,6-DIMETHYL-2-MERCAPTOPYRIDINE
• Ethyl 3-cyano-2-mercapto-6-methylisonicotinate
• 5-CYANO-2-METHYLPYRIDINE
• 2-CHLORO-3-CYANO-6-METHYLPYRIDINE,2-CHLORO-3-CYANO-6-METHYLPYRIDINE 99%
• 2-Chloro-3-cyano-4,6-dimethylpyridine
• 3-Cyano-2,6-Dichloro-4-Methylpyridine 2,6-Dichloro-3-Cyano-4-Methylpyridine,2,6-DICHLORO-3-CYANO-4-METHYLPYRIDINE
• Ethyl 2-chloro-5-cyano-6-Methylnicotinate
• 3-CYANO-5-METHYLPYRIDINE
• 3-Methylpicolinonitrile
• 6-Methylpyridine-2-carbonitrile
• 3-Cyano-2-methylpyridine
• 2-CYANO-5-METHYLPYRIDINE (2-CYANO-5-PICOLINE),2-CYANO-5-METHYLPYRIDINE
• 3-CYANO-4-METHYLPYRIDINE
• 4-CYANO-2-METHYLPYRIDINE
• 2-CYANO-4-METHYLPYRIDINE (2-CYANO-4-PICOLINE),2-Cyano-4-methylpyridine, 4-Methyl-2-cyanopyridine,2-Cyano-4-methylpyridine ,98%,2-CYANO-4-METHYLPYRIDINE
• 6-AMINO-3-CYANO-2-METHYLPYRIDINE,6-Amino-3-cyano-2-methylpyridine 97%
• 2,6-DIHYDROXY-3-CYANO-4-METHYLPYRIDINE