3-Bromo-4-methylpyridine Chemical Properties

Boiling point:

199-200 °C(lit.)

Density 

1.549 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.56(lit.)

Flash point:

175 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol

pka

3.54±0.18(Predicted)

form 

Liquid

Specific Gravity

1.549

color 

Clear colorless to yellow

BRN 

878354

InChI

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

InChIKey

GSQZOLXWFQQJHJ-UHFFFAOYSA-N

SMILES

C1=NC=CC(C)=C1Br

CAS DataBase Reference

3430-22-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-2636

RIDADR 

Cool, dry,tightly closed

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:4-Methyl-3-bromopyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Bromo-4-methylpyridine Usage And Synthesis

Chemical Properties

Clear Liquid

Uses

An intermediate of pyridinyl pyrrole compounds as proton pump inhibitors with improved gastric acid secretion suppressive activity

Uses

3-Bromo-4-methylpyridine may be used as a building block in the preparation of:

• substituted 4-(2,2-diphenylethyl)pyridine-N-oxides for use as potent phosphodiesterase type 4 (PDE4) inhibitors
• benzodiazepine site ligands bearing tricyclic pyridone moiety for human GABA_A receptor
• a novel isomer of ascididemin
• 3-bromopyridine-4-carbonitrile

Synthesis

The general procedure for the synthesis of 4-methyl-3-bromopyridine from 4-methylpyridine was as follows: 0.054 mol of 4-methylpyridine was added to a 60 mL constant pressure dropping funnel. Under nitrogen protection and stirring conditions at room temperature, it was slowly added dropwise to a mixture consisting of 0.07 mol AlCl3 and 0.01 mol potassium bromide, and the reaction mixture was stirred for 1 hour. A condensing unit was installed, heated to 120°C, and 0.07 mol of bromine was added slowly dropwise for about 1 hour dropwise. Heating and stirring were continued at 120°C for 26 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and slowly poured into crushed ice with stirring. The pH was adjusted to neutral by the addition of sodium hydroxide solution and stirred until completely dissolved. The aqueous layer was extracted with dichloromethane, the organic layers were combined and the solvent was recovered by steam distillation. The resulting oily product was purified by column chromatography (eluent ratio of VP petroleum ether: ethyl acetate = 6:1) to give 5.3 g of 3-bromo-4-methylpyridine in the form of a tan oil with a purity of 99.9% and a yield of 57%.

References

[1] Patent: CN106243022, 2016, A. Location in patent: Paragraph 0067-0069
[2] Patent: WO2014/97150, 2014, A1. Location in patent: Page/Page column 22-23
[3] Patent: US2005/80085, 2005, A1. Location in patent: Page/Page column 12
[4] Patent: US5294610, 1994, A

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