2-Amino-5-bromopyridine Chemical Properties

Melting point:

133-138 °C (lit.)

Boiling point:

230.9±20.0 °C(Predicted)

Density 

1.6065 (rough estimate)

refractive index 

1.5182 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.65±0.13(Predicted)

form 

Crystalline Powder

color 

White to beige

Water Solubility 

Soluble in methanol, chloroform, ethyl acetate. Slightly soluble in water.

BRN 

108737

InChI

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

InChIKey

WGOLHUGPTDEKCF-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1

CAS DataBase Reference

1072-97-5(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-5-bromopyridine (1072-97-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

2

F 

10

HazardClass 

IRRITANT

HS Code 

29333999

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

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2-Amino-5-bromopyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Amino-5-bromopyridine is used for the synthesis of polycyclic azaarenes.

General Description

2-Amino-5-bromopyridine is a brominated aromatic amine reagent and is used for labeling of model reducing-end oligosaccharides via reductive amination.

Synthesis

General procedure for the synthesis of 2-amino-5-bromopyridine from 5-bromo-2-nitropyridine: 5-bromo-2-nitropyridine (0.6 mmol), 5 wt% Pd/C (0.5 mol%, 0.003 mmol), H2O (10 equiv, 6.0 mmol), B2(OH)4 (3.3 equiv, 2.0 mmol) and CH3CN ( 1.0 mL) were added to a 10 mL reaction tube. The reaction mixture was stirred at 50 °C for 24 hours. The progress of the reaction was monitored by TLC and when the reaction was complete, the mixture was cooled to room temperature. Water (5 mL) was added and extracted with EtOAc (3 x 5 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the target product 2-amino-5-bromopyridine (55 mg, 99% yield).

References

[1] Tetrahedron, 2017, vol. 73, # 27-28, p. 3898 - 3904
[2] Organic Process Research and Development, 2017, vol. 21, # 2, p. 247 - 252
[3] Organic Letters, 2016, vol. 18, # 11, p. 2774 - 2776
[4] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[5] Yakugaku Zasshi, 1952, vol. 72, p. 381

2-Amino-5-bromopyridine(1072-97-5)Related Product Information

• 2-Chloro-3-cyanopyridine
• Triethanolamine
• 4-Dimethylaminopyridine
• N-Ethylmethylamine
• Bis(2-ethylhexyl)amine
• 2-Aminopyridine
• Dibenzylamine
• 1-Hexadecylpyridinium bromide
• ALTRENOGEST
• 3-Aminopyridine
• 6-Aminocaproic acid
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane
• Triethylamine
• Glycine
• 3-AMINO-5-BROMOPYRIDINE
• 2-(5-BROMO-2-PYRIDYLAZO)-5-(DIETHYLAMINO)PHENOL
• 2-Amino-5-bromo-3-methylpyridine