3-Bromo-2-pyridinamine Chemical Properties

Melting point:

63-67 °C

Boiling point:

232.0±20.0 °C(Predicted)

Density 

1.6065 (rough estimate)

vapor pressure 

0.83-1.8Pa at 20-25℃

refractive index 

1.5182 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Powder

pka

4.14±0.36(Predicted)

color 

Gray to brown

BRN 

109867

InChI

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

InChIKey

RBCARPJOEUEZLS-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC=C1Br

LogP

1.5 at 20℃ and pH7

CAS DataBase Reference

13534-99-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

II

HS Code 

29333990

MSDS

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

3-Bromo-2-pyridinamine Usage And Synthesis

Chemical Properties

grey to brown powder

Uses

2-Amino-3-bromopyridine may be used to synthesize:

• 2-acylamido-3-bromopyridines
• 2-anilino-3-bromopyridine
• 3-[(2-methoxyphenyl)ethynyl]pyridin-2-amine
• 3-[(4-methoxyphenyl)ethynyl]pyridin-2-amine
• N-(bromopyridyl)amidines
• carbolines via palladium catalyzed arylation followed by palladium catalyzed amination reaction
• 2-amino-3-cyanopyridine via palladium catalyzed cyanation reaction with potassium ferro-cyanide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene [DBU]
• nitro-substituted N,N′-dipyridinylamines via palladium catalyzed coupling reaction with 2-chloro-3-nitropyridine in the presence of Xantphos ligand
• 2-amino-3-iodopyridine via reaction with sodium iodide in the presence of copper(I)iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine

Synthesis

General procedure for the synthesis of 2-amino-3-bromopyridine from 3-bromo-5-iodopyridin-2-amine: 30 g of 3-bromo-5-iodopyridin-2-amine and 300 ml of ethanol were added to a reaction flask with 1 g of palladium/silica catalyst. The air in the reaction flask was first replaced three times with nitrogen and then three times with hydrogen. The reaction pressure was adjusted from 0.05 MPa to 0.1 MPa and the reaction temperature was controlled between 20 °C and 30 °C until the raw materials were completely reacted. After the reaction was completed, the catalyst was recovered by filtration. The reaction solution was concentrated to remove some of the solvent and diluted by adding 300 ml of water. Subsequently, 4.2 g of sodium hydroxide was added for neutralization and cooled to 0 °C to 5 °C. The precipitated solid was filtered and dried to give 16.8 g of 3-bromopyridin-2-amine in 97% yield.

References

[1] Patent: CN106432068, 2017, A. Location in patent: Paragraph 0037; 0039; 0040; 0041

3-Bromo-2-pyridinamine(13534-99-1)Related Product Information

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• 4-Dimethylaminopyridine
• Glycine
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• ALTRENOGEST
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• 2-AMINO-3,5-DIBROMO-6-METHYLPYRIDINE
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• 2,6-DIAMINO-3-BROMOPYRIDINE
• ETHYL 3-(2-AMINO-5-BROMOPYRIDIN-3-YL)ACRYLATE
• 4-(3,5-DIBROMO-2-PYRIDYLAZO)-1,3-PHENYLENEDIAMINE