5-Bromo-2-methylpyridine Chemical Properties

Melting point:

32-36 °C

Boiling point:

74 °C / 17mmHg

Density 

1.494±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

3.59±0.10(Predicted)

color 

Off-White to Light Yellow

BRN 

107324

InChI

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

InChIKey

OFKWIQJLYCKDNY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3430-13-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

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

5-Bromo-2-methylpyridine Usage And Synthesis

Description

It is an important intermediate in the organic synthesis, which has many applications, such as pharmaceutical intermediate, organic synthesis, organic solvent, production of dyes, pesticide, and spice. Specifically, this chemical can act as the raw material to prepare 2:2’-dipyridyl and its derivatives.¹ Moreover, this compound may be involved in the synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle.² In addition, 5-bromo-2-methylpyridine has been demonstrated to function as the substrate in a general palladium-catalyzed coupling of aryl bromides/triflates and thiols.³ Besides, this substance can facilitate the synthesis of 5-arylamino-2-picolines via displacement of bromide by anthranilic acid and decarboxylation.⁴

Referrence

1. Willink, H. D. T.; Wibaut, J. P., The preparation of 2 : 2'-dipyridyl and some of its derivatives. Recueil Des Travaux Chimiques Des Pays-Bas 1935, 54, 275-283.
2. Wang, L. H.; Cui, X. L.; Li, J. Y.; Wu, Y. S.; Zhu, Z. W.; Wu, Y. J., Synthesis of Biaryls through a One-Pot Tandem Borylation/Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by a Palladacycle. Eur. J. Org. Chem. 2012, 595-603.
3. Itoh, T.; Mase, T., A general palladium-catalyzed coupling of aryl bromides/triflates and thiols. Org. Lett. 2004, 6, 4587-4590.
4. Louis H. Peterson; Tolman, R. L., Reinvestigation of the synthesis of 5-arylamino-2-picolines J. Heterocycl. Chem. 1977.

Chemical Properties

Light yellow Cryst

Uses

5-Bromo-2-picoline is a halogenated pyridine derivative used is a building block in the preparation of nitrogen containing heterocyclic compounds.

Synthesis

The synthesis method comprises the following steps: reacting diethyl malonate with alkali metal to generate salts, dripping 5-nitryl-2-chloropyridine into the salts for condensation reaction, and subsequently performing decarboxylation on the obtained product under acidic condition to obtain 5-nitryl-2-methylpyridine; performing hydrogenation reduction on the 5-nitryl-2-methylpyridine under the catalysis of Pd/C catalyst to obtain 5-amido-2-methylpyridine; and reacting the 5-amido-2-methylpyridine with acid to generate salts, dripping bromine, dripping a sodium nitrite water solution, and obtaining the 5-bromo-2-methylpyridine.

5-Bromo-2-methylpyridine(3430-13-5)Related Product Information

• 5-Bromo-2-hydroxymethylpyridine
• 5-Bromo-2-methoxypyridine
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• 5-Bromo-2-methylpyridine
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• 5-bromo-2-pyridinecarboxylic acid ethyl ester
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• 6-AMINO-5-BROMO-2-PICOLINE
• 5-BROMO-2-METHYLPYRIDINE N-OXIDE
• 3,5-DIBROMO-2,4,6-TRIMETHYLPYRIDINE
• 2-CHLORO-3-BROMO-6-PICOLINE
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• 2-FLUORO-3-BROMO-6-PICOLINE
• 2,3-DIBROMO-6-PICOLINE
• 3-AMINO-2-BROMO-5-PICOLINE