4-Amino-2,6-dichloropyridine Chemical Properties

Melting point:

169-173 °C (lit.)

Boiling point:

336.7±37.0 °C(Predicted)

Density 

1.497±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Powder

pka

0.49±0.50(Predicted)

color 

White to buff

BRN 

114351

InChI

InChI=1S/C5H4Cl2N2/c6-4-1-3(8)2-5(7)9-4/h1-2H,(H2,8,9)

InChIKey

WAEZOSSWRXDWAX-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=CC(N)=C1

CAS DataBase Reference

2587-02-2(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 4-amino-2,6-dichloro-(2587-02-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

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

4-Amino-2,6-dichloropyridine Usage And Synthesis

Chemical Properties

White solid

Uses

4-Amino-2,6-dichloropyridine is a compound useful in organic synthesis used in the synthesis of Rho kinase inhibitors.

Application

4-Amino-2,6-dichloropyridine has wide applications in the pharmaceutical field. Because its molecule contains amino and chlorine atoms, it can interact with a variety of biomolecules, thus serving as a raw material for the synthesis of many drugs. For example, it can be used to synthesize certain antibiotics, anticancer drugs, and antiviral drugs. These drugs play an important role in the treatment of many diseases.

Synthesis

The general procedure for the synthesis of 4-amino-2,6-dichloropyridine from 2,6-dichloro-4-nitropyridine was as follows: to a solution of 2,6-dichloro-4-nitropyridine (14.82 g, 76.79 mmol) in ethanol (350 mL) was added sequentially iron powder (19.91 g, 356.58 mmol), water (65.8 mL, 3.6 mol), and concentrated hydrochloric acid (14.1 mL, 464.1 mmol). The reaction was carried out at 95 °C with stirring for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature and the pH was adjusted to neutral. After filtration, the filtrate was concentrated and extracted with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to afford 11.9 g of the title product 4-amino-2,6-dichloropyridine in 95.1% yield.

References

[1] Patent: US2012/289497, 2012, A1. Location in patent: Page/Page column 51-52
[2] Patent: EP2524917, 2012, A1. Location in patent: Page/Page column 58-59
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1511 - 1530
[4] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 12, p. 2133 - 2144
[5] ChemCatChem, 2016, vol. 8, # 8, p. 1485 - 1489

4-Amino-2,6-dichloropyridine(2587-02-2)Related Product Information

• ALTRENOGEST
• Bis(2-ethylhexyl)amine
• 2,6-Diaminopyridine
• Clopyralid
• Aniline
• 2,6-Lutidine
• Betaine
• 2-Aminopyridine
• 2-Chloro-5-chloromethylpyridine
• Glycine
• 2,5-Dichloropyridine
• 3-Aminopyridine
• 4-Dimethylaminopyridine
• 4-Aminopyridine
• 2,3-Dichloropyridine
• 2,6-Dichloropyridine
• 2,6-DICHLORO-4-ISOCYANATOPYRIDINE
• 3-AMINO-2,6-DICHLOROPYRIDINE