5-Amino-2-bromopyridine Chemical Properties

Melting point:

75 °C

Boiling point:

180 °C

Density 

1.6065 (rough estimate)

refractive index 

1.5182 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

1.87±0.10(Predicted)

form 

Powder

color 

Beige to brown-black

BRN 

109102

InChI

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

InChIKey

XTHKRYHULUJQHN-UHFFFAOYSA-N

SMILES

C1=NC(Br)=CC=C1N

CAS DataBase Reference

13534-97-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29333990

MSDS

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

5-Amino-2-bromopyridine Usage And Synthesis

Chemical Properties

Light yellow needles

Uses

3-Amino-6-bromopyridine may undergo polymerization via Buchwald–Hartwig amination in the presence of sodium tert-butoxide and XPhos(2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) ligand yielding para-linked and meta-linked polyaminopyridines.

General Description

3-Amino-6-bromopyridine can be synthesized via bromination of 3-aminopyridine using N-bromosuccinimide in acetonitrile.

Synthesis

General procedure for the synthesis of 5-amino-2-bromopyridine from 2-bromo-5-nitropyridine: To a solution of 2-bromo-5-nitropyridine (2.03 g, 10 mmol) in ethanol (48 mL) was added sequentially iron powder (2.8 g, 50 mmol), concentrated hydrochloric acid (1.9 mL) and water (9.1 mL). The reaction mixture was stirred under reflux conditions for 5 hours. After completion of the reaction, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure, the pH was adjusted to 7-8 with base and subsequently extracted with dichloromethane (DCM). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the reddish brown solid product 5-amino-2-bromopyridine (1.58 g, 91.3% yield).

References

[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Green Chemistry, 2018, vol. 20, # 1, p. 130 - 135
[3] Journal of Organic Chemistry, 2011, vol. 76, # 23, p. 9841 - 9844
[4] Patent: EP2886540, 2015, A1. Location in patent: Paragraph 0143; 0144
[5] Patent: US2014/93505, 2014, A1. Location in patent: Page/Page column

5-Amino-2-bromopyridine(13534-97-9)Related Product Information

• 2-Bromo-5-chloropyridine
• ALTRENOGEST
• 2,6-Diaminopyridine
• 4-Dimethylaminopyridine
• 3-Aminopyridine
• 4-Aminopyridine
• 2-Bromo-5-fluoropyridine
• 6-Aminocaproic acid
• 2-Bromo-5-nitropyridine
• 2-Bromopyridine
• Glycine
• 2-Aminopyridine
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane
• 2-BROMO-5-METHOXYPYRIDINE
• 2-Bromo-5-methylpyridine
• 2-Bromo-6-(trifluoromethyl)pyridine
• 2-Bromo-6-methylpyridine