4-Bromo-2-methylpyridine Chemical Properties

Melting point:

26-27°

Boiling point:

76 °C / 14mmHg

Density 

1.450 g/mL at 25 °C

refractive index 

n 20/D 1.556

Flash point:

174 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Dichloromethane

form 

Pale Yellow Liquid

pka

4.38±0.10(Predicted)

color 

Colorless to Light yellow to Light orange

Water Solubility 

Miscible with dichloromethane. Immiscible with water.

InChI

InChI=1S/C6H6BrN/c1-5-4-6(7)2-3-8-5/h2-4H,1H3

InChIKey

JFBMFWHEXBLFCR-UHFFFAOYSA-N

SMILES

C1(C)=NC=CC(Br)=C1

CAS DataBase Reference

22282-99-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-36/37/38-20/21/22

Safety Statements 

26-36/39-36

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

4-Bromo-2-methylpyridine Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

4-Bromo-2-methylpyridine is used as a starting material in the preparation of crown-ester-bipyridines and viologens through sodium or nickel reductive coupling, side chain oxidation and esterification. Further, it serves as an important raw material and intermediate in organic synthesis, pharmaceuticals, agrochemicals and in dyes.

Uses

4-Bromo-2-methylpyridine is a starting material used in a synthesis of crown-ester-bipyridines and viologens via sodium or nickel reductive coupling, side chain oxidation and esterification.

Uses

Used in the preparation of phenyloxadiazolyl pyridines as immunomodulating agents.

Synthesis

2-Methyl-4-aminopyridine (152) (10.1 g, 93.4 mmol) was used as a raw material, which was dissolved in 48% aqueous hydrobromic acid (165 mL) at -10°C and stirred to form a solution. An aqueous solution of sodium nitrite (7.04 g, 0.102 mol) pre-cooled to 0°C (165 mL) was added dropwise to this solution over a period of 0.5 hours. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 16 hours. Upon completion of the reaction, the reaction mixture was diluted with 4 M sodium hydroxide solution (400 mL) and subsequently extracted with tert-butyl methyl ether (TBME). All TBME phases were combined, dried with anhydrous magnesium sulfate and finally concentrated under vacuum to give the target product 4-bromo-2-methylpyridine (153). Yield: 14.8 g (92% yield).LC/MS analysis: retention time 0.57 min, mass spectrum (ES+) m/z 172, 174 ([M+H]+).

References

[1] Patent: WO2008/57497, 2008, A2. Location in patent: Page/Page column 292
[2] Patent: WO2007/89669, 2007, A2. Location in patent: Page/Page column 203-204
[3] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 292
[4] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 292
[5] Patent: WO2004/14913, 2004, A2. Location in patent: Page 81-82

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