3-Amino-6-cyanopyridine Chemical Properties

Melting point:

148-152 °C(lit.)

Boiling point:

368.2±27.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

0.61±0.10(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C6H5N3/c7-3-6-2-1-5(8)4-9-6/h1-2,4H,8H2

InChIKey

IFOXWHQFTSCNQB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

55338-73-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

RIDADR 

3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich

3-Amino-6-cyanopyridine Usage And Synthesis

Chemical Properties

Brown powder

Uses

5-Amino-2-pyridinecarbonitrile (5-Amino-2-cyanopyridine) may be used to synthesize 5-amino-2-pyridine.

Synthesis

The general procedure for the synthesis of 3-amino-6-cyanopyridine from 2-cyano-5-nitropyridine was as follows: to a solution of 5-nitropyridine-2-carbonitrile (7.0 g, 46.9 mmol) in methanol (150 mL) was added 10% palladium carbon catalyst (2.0 g) and ammonium carbamate (7.0 g, 115 mmol). The reaction mixture was heated under reflux conditions for 16 hours. Upon completion of the reaction, the mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure. The concentrated residue was dissolved in water (150 mL) and subsequently extracted with ethyl acetate (150 mL × 3). The organic layers were combined, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 5.1 g of 5-aminopyridine-2-carbonitrile in 91.3% yield.

References

[1] Patent: WO2015/22301, 2015, A1. Location in patent: Page/Page column 28
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 18 - 25
[3] Organic Process Research and Development, 2004, vol. 8, # 1, p. 62 - 71
[4] Patent: CN106810494, 2017, A. Location in patent: Paragraph 0030; 0031
[5] Patent: WO2017/184547, 2017, A1. Location in patent: Paragraph 00384

3-Amino-6-cyanopyridine(55338-73-3)Related Product Information

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