2-Bromo-6-methylpyridine

Chemical Properties

Light yellow liquid

Uses

2-Bromo-6-methylpyridine may be used in the synthesis of the following:

• 6,6′-dimethyl-2,2′-bipyridine
• 6-methyl-2-pyridyl-2-pyridylmethanone
• 2-methyl-6-(trimethylsilyl)-pyridine
• N,N′-bis-(6-methylpyrid-2-yl)-(1R,2R)-1,2- diaminocyclohexane (cydiampy)
• 2-methyl-6-(trimethylstannanyl)pyridine
• 2-(6-methylpyridin-2-yl)propan-2-ol
• bis[(2-bromo-6-methylpyridinium)hexafluorosilicate] monohydrate

Uses

2-Bromo-6-methylpyridine is a halogenated pyridine derivative used is a building block in the preparation of nitrogen containing heterocyclic compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 3168, 1954 DOI: 10.1021/ja01641a017

General Description

2-Bromo-6-methylpyridine is a bromopyridine derivative. It is formed when 2-chloro-6-methylpyridine is heated with bromotrimethylsilane. Its synthesis from various methods have been reported.

Synthesis

The following are the steps for preparing 2-Bromo-6-methylpyridine:
Step 1: 2-Amino-6-methylpyridine With hydrogen bromide; bromine at -10~5℃ for 1.5h;
Step 2: With NaNO2 In water monomer at -10~5℃ for 1.5h;
Step 3: With sodium hydroxide In water monomer at -10℃.

References

[1] Patent: CN105384684, 2016, A. Location in patent: Paragraph 0028; 0029
[2] Organic Letters, 2000, vol. 2, # 21, p. 3373 - 3376
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 11, p. 2579 - 2587
[4] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[5] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 19, p. 3151 - 3155