2,6-Bis(bromomethyl)pyridine
[CAS# 7703-74-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Methylpyridine
• Name: 2,6-Bis(bromomethyl)pyridine
• Synonyms: 2,6-Di(bromomethyl)pyridine; alpha,alpha'-Dibromo-2,6-lutidine
• Molecular Formula: C₇H₇Br₂N
• Molecular Weight: 264.95
• CAS Registry Number: 7703-74-4
• EC Number: 628-946-5
• SMILES: C1=CC(=NC(=C1)CBr)CBr

Properties

• Solubility: Slightly soluble (2.2 g/L) (25 ºC), Calc.^*
• Density: 1.870±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 88-89 ºC (pentane )^**
• Boiling point: 275.6±30.0 ºC (760 Torr), Calc.^*
• Flash point: 120.5±24.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Kaptein, Bernard; Journal of Organic Chemistry 1990, V55(6), P1890-901.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2,6-Bis(bromomethyl)pyridine is an organic compound with the molecular formula C7H8Br2N. It is a derivative of pyridine, a heterocyclic aromatic compound containing nitrogen, with bromomethyl groups (-CH2Br) attached at the 2 and 6 positions of the pyridine ring. The compound is commonly used as a building block in organic synthesis, particularly for the development of more complex molecules used in various chemical applications.

The synthesis of 2,6-bis(bromomethyl)pyridine typically involves the reaction of pyridine with bromomethylating agents, such as formaldehyde and hydrogen bromide (HBr), under controlled conditions. The bromomethyl groups are introduced at the 2 and 6 positions of the pyridine ring, resulting in the formation of the desired bis(bromomethyl) derivative. The reaction can be carried out in the presence of a base to facilitate the formation of the C-H bonds needed for the bromomethylation process.

Due to the presence of two bromomethyl groups, 2,6-bis(bromomethyl)pyridine is highly reactive and can undergo a variety of chemical reactions. The bromomethyl groups serve as electrophilic centers that can readily participate in nucleophilic substitution reactions, where they can be replaced by various nucleophiles such as amines, alcohols, or thiols. This reactivity makes 2,6-bis(bromomethyl)pyridine a useful intermediate in the synthesis of a wide range of compounds, including ligands, pharmaceuticals, and functional materials.

One of the primary applications of 2,6-bis(bromomethyl)pyridine is in the synthesis of coordination compounds, particularly those involving metal ions. The pyridine ring itself is a known ligand that can coordinate to metal centers, and the bromomethyl groups provide additional sites for further functionalization. These types of compounds have potential applications in catalysis, where metal complexes can act as catalysts for a variety of chemical reactions, including organic transformations and polymerizations.

Additionally, 2,6-bis(bromomethyl)pyridine is used in the preparation of polymeric materials, where it can serve as a cross-linking agent. The reactive bromomethyl groups can form covalent bonds with other monomers or polymers, leading to the creation of networked structures with specific mechanical or chemical properties. This feature is particularly useful in the development of functional coatings, resins, or materials with specialized surface properties.

In the field of medicinal chemistry, 2,6-bis(bromomethyl)pyridine can be used as a precursor in the synthesis of biologically active compounds. The reactivity of the bromomethyl groups allows for the introduction of various substituents, potentially leading to the development of new pharmaceutical agents. By modifying the pyridine ring or attaching different functional groups, researchers can create molecules with specific bioactivity, such as antimicrobial or anticancer properties.

Another area of interest for 2,6-bis(bromomethyl)pyridine is in the preparation of sensors and detection systems. Due to the ability to functionalize the pyridine ring and bromomethyl groups, this compound can be incorporated into materials designed to detect various analytes, such as metal ions, gases, or organic compounds. The reactivity of the bromomethyl groups can be exploited to develop selective sensing platforms with enhanced sensitivity.

Despite its reactivity and useful applications, 2,6-bis(bromomethyl)pyridine must be handled with caution. The bromomethyl groups are highly reactive and can cause irritation or burns upon contact with skin or mucous membranes. Proper safety protocols should be followed when working with this compound, including the use of personal protective equipment (PPE) such as gloves, goggles, and lab coats, as well as working in well-ventilated areas to minimize exposure to fumes.

In summary, 2,6-bis(bromomethyl)pyridine is a versatile compound that plays an important role as an intermediate in the synthesis of a variety of functionalized materials, coordination complexes, and biologically active molecules. Its high reactivity, particularly due to the presence of bromomethyl groups, makes it valuable for organic synthesis and materials science. However, as with many reactive chemical intermediates, care should be taken during its handling to ensure safety in laboratory and industrial settings.

References

1980. Sequence of replacement of hydrogen in 2,6-dimethylpyridine by lithium or halogen. Chemistry of Heterocyclic Compounds, 16(1).
DOI: 10.1007/bf00475401

2005. A New Synthetic Method for (Aza)n[3n]cyclophanes by Diethyl Phosphoramidates. Synthesis, 2005(13).
DOI: 10.1055/s-2005-872171

2010. 5,8-Dibromo-2,11-dithia-pyridino-paracyclo-phane. Acta Crystallographica. Section E, Structure Reports Online, 66(Pt 8).
DOI: 10.1107/s1600536810028850