2-Amino-5-bromo-4-methylpyridine Chemical Properties

Melting point:

148-151 °C (lit.)

Boiling point:

254.2±35.0 °C(Predicted)

Density 

1.5672 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in methanol.

pka

5.27±0.24(Predicted)

form 

Powder

color 

Cream

InChI

InChI=1S/C6H7BrN2/c1-4-2-6(8)9-3-5(4)7/h2-3H,1H3,(H2,8,9)

InChIKey

JDNCMHOKWINDKI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

98198-48-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

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

2-Amino-5-bromo-4-methylpyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Amino-5-bromo-4-methylpyridine is used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2-amino-5-bromo-4-methylpyridine from 2-amino-4-methylpyridine: 2-amino-4-methylpyridine (0.5 mmol, 1.0 eq.), p-toluenesulfonic acid (p-TSA, 0.4 mmol, 0.8 eq.), and brominated 1-butylpyridine (1.5 mmol, 3.0 eq.) were added to a 50 mL Schlenk tube ) were added to the mixture. Under air atmosphere, 2-dimethoxyethane (2 mL) was added as solvent. Subsequently, hydrogen peroxide (H2O2, 1.2 mmol, 2.4 eq.) was slowly added to the reaction system. The reaction mixture was stirred at 80 °C for 24 hours. Upon completion of the reaction, the mixture was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate) to afford the target product 2-amino-5-bromo-4-methylpyridine.

References

[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 22, p. 7958 - 7966
[2] Tetrahedron Letters, 2014, vol. 55, # 36, p. 5058 - 5061
[3] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 4, p. 569 - 574
[4] Synthetic Communications, 1999, vol. 29, # 1, p. 103 - 110
[5] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 1151 - 1175

2-Amino-5-bromo-4-methylpyridine(98198-48-2)Related Product Information

• Methyl acrylate
• Methyl acetate
• Basic Violet 1
• Acetonitrile
• 4-Dimethylaminopyridine
• 3-Bromo-4-methylpyridine
• 4-Methylpyridine
• Methylparaben
• 2-Aminopyridine
• 1-Hexadecylpyridinium bromide
• 2-Bromo-4-methylpyridine
• 2-Amino-5-methylpyridine
• Paraquat dichloride
• Kresoxim-methyl
• 4-Methylpyridin-2-amine
• 2-Amino-5-bromopyridine
• ALTRENOGEST
• Glycine