6-CYANONICOTINIC ACID Chemical Properties

Melting point:

190-194 °C(lit.)

Boiling point:

395.9±27.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in alcohol.

form 

Oil

pka

2.81±0.10(Predicted)

color 

Clear Yellow

BRN 

4384027

CAS DataBase Reference

70165-31-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-CYANONICOTINIC ACID Usage And Synthesis

Uses

6-Cyanonicotinic acid, is used in medicine

Synthesis

The general procedure for the synthesis of 6-cyanonicotinic acid from oxonicotinic acid and sodium cyanide was as follows: to a 1.2 L DMF solution of oxonicotinic acid N-oxide (51 g, 0.37 mol) was added sodium cyanide (54 g, 1.1 mol), triethylamine (255 mL, 1.83 mol), and trimethylchlorosilane (185 mL). The reaction mixture was stirred at 110 °C for 10 h. After completion of the reaction, filtration was performed and the filtrate was concentrated. The residue was dissolved in 100 mL of 2N hydrochloric acid and extracted with dichloromethane. The organic layers were combined, concentrated and recrystallized from water to give 12 g (22% yield) of 6-cyanonicotinic acid.

References

[1] Synthesis, 1983, # 4, p. 316 - 319
[2] Chemical Communications, 2004, # 15, p. 1770 - 1771
[3] Patent: WO2003/101956, 2003, A1. Location in patent: Page 113; 114
[4] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 4, p. 385 - 389

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