2-Amino-6-bromopyridine Chemical Properties

Melting point:

88-91 °C (lit.)

Boiling point:

273.0±20.0 °C(Predicted)

Density 

1.710±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Very Slightly)

pka

2.73±0.24(Predicted)

form 

Powder

color 

Slightly yellow to light brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H5BrN2/c6-4-2-1-3-5(7)8-4/h1-3H,(H2,7,8)

InChIKey

BKLJUYPLUWUEOQ-UHFFFAOYSA-N

SMILES

C1(N)=NC(Br)=CC=C1

CAS DataBase Reference

19798-81-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-Amino-6-bromopyridine Usage And Synthesis

Chemical Properties

Slightly yellow to light brown powder

Uses

Employed in an efficient one-pot synthesis of 7-azaindoles. Used in the synthesis of anti-HIV agents.

Uses

2-Amino-6-bromopyridine is a disubstituted pyridine used as a building block in the preparation of nitrogen containing bicyclic and polycylic compounds.

Application

2-Amino-6-bromopyridine is an important raw material for the synthesis of:
2-amino-6-diethylaminopyridine
2,6-di-(methylamino)-pyridine
3-(6-bromopyridin-2-yl)-2-(2,6-difluorophenyl)-1,3-thiazolidin-4-one
N-(6-bromopyridin-2-yl)dodecylamide
2-bromo-6-iodopyridine
Employed in an efficient one-pot synthesis of 7-azaindoles.
Used in the synthesis of anti-HIV agents.

General Description

2-Amino- 6-bromopyridine has been synthesized from epichlorohydrin.

Synthesis

14.1 Preparation of 6-bromo-2-aminopyridine In a steel autoclave equipped with a glass liner, 10.00 g of 2,6-dibromopyridine (42.2 mmol) was suspended in 50 mL of concentrated ammonia. The autoclave was sealed and heated to 190°C using a heating jacket and maintained for 6 hours (pressure was raised to about 25 bar). After the autoclave was cooled and depressurized, the reaction mixture was mixed with 100 mL of ethyl acetate for phase separation. The aqueous phase was extracted twice with ethyl acetate, 100 mL each. the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in 250 mL of a solvent mixture of cyclohexane/ethyl acetate (1:1, v/v) to remove the by-product 2,6-diaminopyridine. Subsequently, the solution was filtered through a short silica gel column (5 x 20 cm) and washed again with 250 mL of cyclohexane/ethyl acetate (1:1, v/v) mixed solvent. After removal of the solvent under reduced pressure, the residue was sublimated at 90°C and 10-1 mbar to give 6.49 g (37.5 mmol, 88.9% yield) of 6-bromo-2-aminopyridine as a white solid.

References

[1] Patent: US2004/199024, 2004, A1. Location in patent: Page 17
[2] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 381,386, 949
[3] Chemical Communications, 2010, vol. 46, # 6, p. 925 - 927

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