3-Amino-5-bromopyridine Chemical Properties

Melting point:

65-69 °C

Boiling point:

149-150 °C(Press: 12 Torr)

Density 

1.710±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.81±0.20(Predicted)

form 

Powder

color 

White to yellow to brown

InChI

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

InChIKey

MDQXGHBCDCOOSM-UHFFFAOYSA-N

SMILES

C1=NC=C(Br)C=C1N

CAS DataBase Reference

13535-01-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,O

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

RIDADR 

Cool, dry,tightly closed

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

3-Amino-5-bromopyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

3-Amino-5-bromopyridine is used in green preparation of tryptamine salicylic acid compounds as antitumor agent.

Synthesis

General procedure for the synthesis of 5-bromo-3-aminopyridine from 5-bromonicotinamide: 1. To a pre-cooled 340 ml aqueous solution containing 31.8 g (0.79 mol) of sodium hydroxide and 40.7 g (0.255 mol) of bromine, 42.0 g (0.209 mol) of commercially available 5-bromonicotinamide was added. 2. The reaction mixture was gradually warmed to room temperature, followed by heating the reaction at 70 °C for 1 hour. 3. Upon completion of the reaction, the resulting brown suspension was allowed to cool to room temperature. 4. The aqueous phase was treated with saturated brine and then extracted three times with a 1:1 solvent mixture of THF and tert-butyl methyl ether. 5. The organic phases were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure. 6. 39.1 g of the dark brown residue obtained from the concentration was purified by fast chromatography (eluent: heptane/ethyl acetate 1:1) to yield 5-bromo-3-aminopyridine as a brown solid (total yield 70.2 g, 70% yield).

References

[1] ChemMedChem, 2014, vol. 9, # 1, p. 217 - 232
[2] Patent: US2006/160857, 2006, A1. Location in patent: Page/Page column 56
[3] Patent: US2006/199960, 2006, A1. Location in patent: Page/Page column 21
[4] Patent: US2006/217387, 2006, A1. Location in patent: Page/Page column 31
[5] Patent: US2003/199511, 2003, A1. Location in patent: Page/Page column 23

3-Amino-5-bromopyridine(13535-01-8)Related Product Information

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