2-(Bromomethyl)naphthalene
[CAS# 939-26-4]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 2-(Bromomethyl)naphthalene
• Molecular Formula: C₁₁H₉Br
• Molecular Weight: 221.10
• CAS Registry Number: 939-26-4
• EC Number: 213-359-5
• SMILES: C1=CC=C2C=C(C=CC2=C1)CBr

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Melting point: 51 - 55 °C (Expl.)
• Boiling point: 293.3 °C 760 mmHg (Calc.)^*, 304.6 °C (Expl.)
• Flash point: 151.8±12.3 °C (Calc.)^*, 110 °C (Expl.)
• Index of refraction: 1.664 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H314-H317
• Safety Statements: P260-P261-P264-P272-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P333+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 3261

Discovery and Applications

2-(Bromomethyl)naphthalene is an organic compound that belongs to the class of halogenated aromatic compounds. Its chemical formula is C9H9Br, and it consists of a naphthalene ring (a polycyclic aromatic hydrocarbon) with a bromomethyl group (-CH2Br) attached to the second carbon of the naphthalene ring. The compound is primarily used as an intermediate in organic synthesis and serves as a building block for the preparation of more complex molecules in various chemical applications.

The synthesis of 2-(bromomethyl)naphthalene generally involves the bromomethylation of naphthalene. This reaction is typically carried out using a bromomethylating agent, such as formaldehyde and hydrogen bromide (HBr), under appropriate reaction conditions. The bromomethyl group is introduced at the 2-position of the naphthalene ring, yielding the desired product. The reaction can be facilitated in the presence of a base or catalyst to promote the formation of the C-H bond necessary for the substitution of a hydrogen atom by the bromomethyl group.

The introduction of the bromomethyl group into the naphthalene ring imparts a high degree of reactivity to the compound, making it a valuable intermediate for further chemical transformations. The bromomethyl group is an electrophilic center that can easily undergo nucleophilic substitution reactions. As a result, 2-(bromomethyl)naphthalene can be used to introduce a wide range of functional groups through reactions with nucleophiles such as amines, alcohols, thiols, and others. This reactivity makes it a useful intermediate in the synthesis of various derivatives of naphthalene with diverse functional properties.

One of the primary applications of 2-(bromomethyl)naphthalene is in the synthesis of complex organic compounds, particularly in the preparation of naphthalene-based molecules for use in pharmaceuticals, agrochemicals, and materials science. By modifying the naphthalene ring or attaching different substituents to the bromomethyl group, chemists can develop a wide range of compounds with specific biological, chemical, or physical properties.

For example, 2-(bromomethyl)naphthalene can be used as a precursor in the synthesis of biologically active molecules, including pharmaceuticals. The reactivity of the bromomethyl group enables the introduction of functional groups that are important for the biological activity of the final compound. The naphthalene core is often found in drugs with applications such as anti-inflammatory, anticancer, and antimicrobial properties. The versatility of 2-(bromomethyl)naphthalene makes it an attractive starting material for drug discovery and development.

In materials science, 2-(bromomethyl)naphthalene is used in the preparation of polymeric materials and molecular sensors. The bromomethyl group can serve as a cross-linking agent in the synthesis of networked polymers, enhancing the mechanical or chemical properties of the resulting material. Additionally, the compound can be functionalized to create sensor systems that detect various analytes, such as metal ions or organic compounds. The ability to incorporate the naphthalene ring into materials and sensors enables the development of novel technologies with specific functionalities.

2-(Bromomethyl)naphthalene also finds applications in the synthesis of dyes, pigments, and fluorescent materials. The naphthalene structure is well-known for its optical properties, and functionalizing it with various groups can modify these properties for use in a variety of applications. The bromomethyl group can be replaced with different nucleophiles to tailor the electronic properties of the molecule, making it useful for applications in organic electronics, photonics, and fluorescence-based sensing.

Despite its usefulness, 2-(bromomethyl)naphthalene should be handled with care. The bromomethyl group is reactive and can cause irritation to the skin, eyes, and respiratory system. It is also a potentially hazardous compound if improperly stored or handled, as it may release harmful vapors or react violently under certain conditions. Standard safety precautions, including the use of protective equipment such as gloves, goggles, and lab coats, are essential when working with this compound. Furthermore, the compound should be stored in a dry, cool place, away from incompatible substances and sources of heat.

In summary, 2-(bromomethyl)naphthalene is a versatile and reactive compound used as an intermediate in organic synthesis. It plays a key role in the preparation of a variety of functionalized naphthalene derivatives that are used in pharmaceuticals, materials science, and other applications. Its high reactivity makes it an attractive building block for chemical transformations, although proper safety measures must be followed when handling this compound.

References

1978. Fragmentation of α-substituted 2-methylnaphthalenes under electron impact. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 27(10).
DOI: 10.1007/bf00946525

2018. Synthesis, Characterization, Thermal Analyses, and Spectroscopic Properties of Novel Naphthyl-Functionalized Imidazolium Ionic Liquids. Russian Journal of Physical Chemistry A, 92(3).
DOI: 10.1134/s0036024418030196

2021. Effect of Copper on the Oxidation Mechanisms of Tertiary and Secondary Amines of Methyl-naphthyl-cyclen-Modified Gold Electrodes. Journal of Inorganic and Organometallic Polymers and Materials, 31(6).
DOI: 10.1007/s10904-020-01864-4