2,4,6-Trimethylbromobenzene
[CAS# 576-83-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 2,4,6-Trimethylbromobenzene
• Synonyms: 2,4,6-Trimethylphenyl bromide; 1-Bromomesitylene; 2-Bromo-1,3,5-trimethylbenzene; 1-Bromo-2,4,6-trimethylbenzene; Mesityl bromide
• Molecular Formula: C₉H₁₁Br
• Molecular Weight: 199.09
• CAS Registry Number: 576-83-0
• EC Number: 209-405-9
• SMILES: CC1=CC(=C(C(=C1)C)Br)C

Properties

• Density: 1.301 g/mL (Expl.)
• Melting point: 2 °C (Expl.)
• Boiling point: 225 °C (Expl.)
• Refractive index: 1.552 (Expl.)
• Flash point: 96 °C (Expl.)

Safety Data

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

Hazard Classification

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

Discovery and Applications

2,4,6-Trimethylbromobenzene is an organic compound derived from benzene, a well-known aromatic hydrocarbon. This compound contains three methyl groups attached to the benzene ring at the 2, 4, and 6 positions, along with a bromine atom at the 1-position. Its chemical formula is C9H11Br, and it is commonly referred to as a halogenated methylbenzene. The compound was first synthesized as part of research into functionalized benzene derivatives, with a particular focus on the introduction of halogen atoms into the benzene ring to modify its reactivity and properties.

The synthesis of 2,4,6-trimethylbromobenzene typically involves the bromination of 2,4,6-trimethylbenzene (mesitylene) using bromine or a bromine-containing reagent, such as NBS (N-Bromosuccinimide), in the presence of a suitable catalyst. The reaction proceeds via an electrophilic aromatic substitution mechanism, where the bromine atom substitutes one of the hydrogens on the benzene ring. The high reactivity of the bromine atom enhances the compound's ability to undergo further reactions, making it a useful intermediate in various synthetic processes.

One of the primary applications of 2,4,6-trimethylbromobenzene is in the field of organic synthesis. The bromine atom attached to the benzene ring serves as a reactive site for further functionalization, allowing the creation of a wide range of derivatives. These derivatives are valuable in the synthesis of other compounds, including pharmaceuticals, agrochemicals, and polymers. For example, the compound can be used as a precursor in the synthesis of various organic molecules, including biologically active compounds, by replacing the bromine atom with other functional groups or through cross-coupling reactions, such as Suzuki or Heck reactions.

2,4,6-Trimethylbromobenzene also plays an important role in the development of materials science. Benzene derivatives, including halogenated methylbenzenes, are used in the manufacture of organic electronic materials, such as organic light-emitting diodes (OLEDs) and organic solar cells (OSCs). The presence of the bromine atom in 2,4,6-trimethylbromobenzene can modify the compound’s electronic properties, making it suitable for incorporation into conjugated materials that exhibit semiconducting properties. The trimethyl group at the 2, 4, and 6 positions of the benzene ring further influences the solubility and stability of the material, making it an ideal candidate for use in electronic devices.

In addition to its use in organic synthesis and materials science, 2,4,6-trimethylbromobenzene has potential applications in the development of novel pharmaceutical agents. Benzene derivatives are commonly investigated for their biological activity, and the presence of the bromine and methyl groups can influence the compound’s interaction with biological targets. While this compound itself may not be directly used in drug development, its derivatives could serve as starting materials for the synthesis of bioactive molecules with potential therapeutic applications. Research has shown that halogenated aromatic compounds can exhibit antibacterial, anticancer, and anti-inflammatory properties, which may make them valuable in medicinal chemistry.

The compound also has a role in the production of fine chemicals and intermediates used in the manufacture of agrochemicals. As with pharmaceuticals, the halogenated nature of the compound can offer enhanced reactivity and selectivity in various chemical reactions, allowing for the design of specialized pesticides or herbicides.

In conclusion, 2,4,6-trimethylbromobenzene is a versatile organic compound with several important applications in organic synthesis, materials science, pharmaceuticals, and agrochemicals. Its ability to serve as a precursor for the production of more complex derivatives, as well as its role in modifying the properties of organic materials, highlights its value in both research and industry.

References

2019. Task-Specific Properties and Prospects of Ionic Liquids in Cross-Coupling Reactions. Topics in current chemistry (Cham), 377(5).
DOI: 10.1007/s41061-019-0255-2

2018. Oxidation of Iodo- and Bromo-Substituted Polymethylbenzenes in the System PbO2–CF3COOH–CH2Cl2. Russian Journal of Organic Chemistry, 54(3).
DOI: 10.1134/s1070428018030053

2016. Recent Advances in Bromination of Aromatic and Heteroaromatic Compounds. Synthesis, 48(03).
DOI: 10.1055/s-0035-1561503