2,6-Dibromotoluene: A Versatile Compound for Chemical Synthesis
2,6-Dibromotoluene is a chemical compound that belongs to the class of halogenated aromatic hydrocarbons. It has the molecular formula C8H7Br2 and the CAS registry number 69321-60-4. As the name suggests, 2,6-dibromotoluene contains two bromine atoms that are substituted at the 2 and 6 positions of a toluene ring. The compound is also known by other names such as 1,3-dibromo-2-methylbenzene, and it has a molar mass of 249.95 g/mol.
The synthesis of 2,6-dibromotoluene can be achieved by several methods, which involve the bromination of toluene or its derivatives. One of the most common procedures is the electrophilic aromatic substitution of toluene with bromine in the presence of a Lewis acid catalyst such as FeBr3 or AlBr3. The reaction results in the formation of a mixture of mono-, di-, and tri-brominated products, which can be separated by distillation or chromatography. Alternatively, 2,6-dibromotoluene can be obtained by the bromination of 2,6-dimethylphenol or 2,6-dimethylbenzyl alcohol, followed by acid-catalyzed dehydration.
2,6-Dibromotoluene is a versatile compound that finds applications in various fields of chemistry. One of its main uses is as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. For example, 2,6-dibromotoluene can be used as a building block for the synthesis of antihypertensive drugs such as losartan and valsartan, which are angiotensin receptor blockers. The compound can also be employed in the preparation of herbicides such as propanil and pyrazolate, which are used to control weeds in crops.
In addition to its role as a synthetic intermediate, 2,6-dibromotoluene has other interesting properties that make it useful in various applications. For instance, the compound has been studied as a potential flame retardant for polymeric materials such as polystyrene and polypropylene. It has been found that the presence of bromine atoms in the aromatic ring of 2,6-dibromotoluene enhances its flame retardancy by inhibiting the formation of free radicals and promoting the formation of char residues.
Another interesting aspect of 2,6-dibromotoluene is its ability to undergo palladium-catalyzed cross-coupling reactions with various nucleophiles such as arylboronic acids, alkynes, and amines. This reaction, known as Suzuki-Miyaura coupling, allows the formation of a carbon-carbon bond between the bromine atom and the nucleophile, leading to the synthesis of diverse organic molecules. For example, 2,6-dibromotoluene has been used as a substrate for the synthesis of polyaromatic hydrocarbons, which are important materials for organic electronics and photovoltaics.
Ningbo Inno Pharmchem Co., Ltd. is a leading manufacturer and supplier of 2,6-dibromotoluene and other fine chemicals in China. The company has a state-of-the-art production facility and a team of experienced chemists who ensure the quality and reliability of their products. Inno Pharmchem offers a wide range of services, including custom synthesis, contract manufacturing, and technical support, to meet the specific needs of its customers.
In conclusion, 2,6-dibromotoluene is a valuable compound that has numerous applications in the fields of pharmaceuticals, agrochemicals, polymers, and organic synthesis. Its unique properties, such as flame retardancy and palladium-catalyzed cross-coupling, make it a versatile building block for the synthesis of diverse molecules. Ningbo Inno Pharmchem Co., Ltd. is a trusted supplier of high-quality 2,6-dibromotoluene and other fine chemicals, and it is committed to providing innovative solutions to its customers.
