5-Amino-2-chloropyridine Chemical Properties

Melting point:

81-83 °C(lit.)

Boiling point:

205.39°C (rough estimate)

Density 

1.2417 (rough estimate)

refractive index 

1.5110 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

1.94±0.10(Predicted)

color 

White to Brown

BRN 

108891

InChI

InChI=1S/C5H5ClN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2

InChIKey

QAJYCQZQLVENRZ-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC=C1N

CAS DataBase Reference

5350-93-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:5-Amino-2-chloropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Amino-2-chloropyridine Usage And Synthesis

Chemical Properties

Light yellow to brown crystalline powder

Uses

5-Amino-2-chloropyridine was used in the synthesis of [²H₅]2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine. It was used in identification and evaluation of molecularly imprinted polymers for the selective removal of potentially genotoxic aminopyridine impurities from pharmaceuticals.

Definition

ChEBI: 3-Amino-6-chloropyridine is an aminopyridine.

General Description

5-Amino-2-chloropyridine undergoes Suzuki-Miyaura coupling with sterically hindered 2,6-dimethylphenylboronic acid. It undergoes facile temperature dependent displacement of chloride by bromide via Sandmeyer reaction to yield 2,5-dibromopyridine.

Synthesis

General method: 2-chloro-5-nitropyridine (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, 2N aqueous hydrochloric acid solution was slowly added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3). The organic layer was extracted three times with saturated aqueous sodium bicarbonate solution and combined. The organic layers were subsequently washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford the target product 2-chloro-5-aminopyridine.

References

[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Organic Letters, 2009, vol. 11, # 6, p. 1345 - 1348
[3] ACS Catalysis, 2014, vol. 4, # 6, p. 1777 - 1782
[4] New Journal of Chemistry, 2015, vol. 39, # 11, p. 8498 - 8504
[5] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649

5-Amino-2-chloropyridine(5350-93-6)Related Product Information

• 4-Dimethylaminopyridine
• ALTRENOGEST
• Clopidol
• 3-Aminophenol
• 2-Chloro-5-chloromethylpyridine
• Glycine
• 3-Aminopyridine
• 6-Aminocaproic acid
• 2-Chloro-5-nitropyridine
• 2-Chloro-3-cyanopyridine
• 2-Aminopyridine
• 2-Chloropyridine
• Tris(hydroxymethyl)aminomethane
• 2-chloro-5-cyanopyridine
• 2-Chloro-5-fluoropyridine
• 3-Bromo-6-chloro-2-methylpyridine
• 5-Bromo-2-chloropyridine
• 6-Chloro-2-methyl-3-nitropyridine