2-Amino-4-cyanopyridine Chemical Properties

Melting point:

146-148°C

Boiling point:

297.7±20.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.93±0.11(Predicted)

Appearance

Off-white to light yellow Solid

Water Solubility 

Slightly soluble in water.

BRN 

386393

InChI

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

InChIKey

GEEAYLFEIFJFGP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

42182-27-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-41-37/38-22

Safety Statements 

26-36/37/39-36-39

RIDADR 

3439

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

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2-Amino-4-cyanopyridine Usage And Synthesis

Chemical Properties

Yellow or pale brown cryst powder

Uses

2-Amino-4-cyanopyridine is used in the treatment of central nervous system (CNS) disorders and as a mGluR2 antagonist.

Uses

2-Amino-4-cyanopyridine is a pyridine derivative as mGluR2 antagonists; used in the treatment of CNS disorders.

Synthesis

Step 5: A mixture of 4-bromopyridin-2-amine (4.9 g, 28.5 mmol), zinc cyanide (5.0 g, 42.5 mmol), tris(dibenzylideneacetone)dipalladium (1.3 g, 1.4 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (1.6 g, 2.8 mmol) was dissolved in N,N-dimethylformamide (150 mL). The reaction mixture was stirred at 100 °C for 1.5 h under nitrogen protection. After completion of the reaction, the mixture was cooled to room temperature and diluted with water (500 mL). The mixture was extracted with ethyl acetate (300 mL x 3). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent petroleum ether/ethyl acetate (10:1 to 2:1) to afford 2-amino-4-cyanopyridine as a light yellow solid (2.7 g, 80% yield).1H NMR (300 MHz, CDCl3) δ 8.19 (d, J = 5.1 Hz, 1H), 6.82 (d, J = 4.8 Hz, 1H) 6.69 (d, J = 0.9 Hz, 1H), 4.72 (br s, 2H).LCMS (ESI) m/z 120 (M + H)+.

References

[1] Patent: EP2766359, 2016, B1. Location in patent: Paragraph 117.5

2-Amino-4-cyanopyridine(42182-27-4)Related Product Information

• 4-Methylpyridin-2-amine
• 4-Cyanopyridine
• ETHYL 2-CYANOACRYLATE
• Glycine
• ALTRENOGEST
• 2,6-Lutidine
• 2-Chloro-3-cyanopyridine
• 4-Dimethylaminopyridine
• 6-Aminocaproic acid
• 3-Cyanopyridine
• 3-Aminophenol
• 3-Aminopyridine
• 2-Aminopyridine
• Tris(hydroxymethyl)aminomethane
• 3-AMINO-4-CYANOPYRIDINE
• 2-Pyrimidinecarbonitrile, 5-amino- (9CI)
• 4-Amino-2-bromopyrimidine-5-carbonitrile
• N'-[6-(4-BROMOPHENYL)-3,4,5-TRICYANO-2-PYRIDINYL]-N,N-DIMETHYLIMINOFORMAMIDE