ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Chloropyridine 4-Amino-2,6-dichloropyridine

4-Amino-2,6-dichloropyridine

Product Name4-Amino-2,6-dichloropyridine
CAS2587-02-2
MFC5H4Cl2N2
MW163
EINECS629-221-6
MOL File2587-02-2.mol

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)
pka	0.49±0.50(Predicted)
form	Powder
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

Provider	Language
SigmaAldrich	English
ALFA	English

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

25194-01-8

2587-02-2

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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