For chemists and researchers involved in organic synthesis, a deep understanding of the chemical properties and reactivity of their building blocks is fundamental. 1,2-Dibromo-4-tert-butylbenzene (CAS 6683-75-6) is a prime example of an intermediate whose utility stems directly from its specific molecular structure and the resulting chemical behavior. This article delves into the intrinsic properties and common reaction pathways associated with this compound, offering technical insights for those looking to buy or utilize it in their work.

Structurally, 1,2-Dibromo-4-tert-butylbenzene is a disubstituted aromatic hydrocarbon. The benzene ring is adorned with two bromine atoms in an ortho position relative to each other, and a tert-butyl group is situated para to one of the bromine atoms. The molecular formula is C10H12Br2, with a molecular weight of approximately 292.01 g/mol. The presence of the tert-butyl group imparts some lipophilicity and steric bulk, influencing solubility and potentially directing regioselectivity in certain reactions. Its typical appearance is as a powder or liquid, depending on purity and temperature, with a high boiling point around 281-282 °C. The density is approximately 1.557 g/mL at 25 °C.

The reactivity of 1,2-Dibromo-4-tert-butylbenzene is primarily governed by the carbon-bromine bonds. These bonds are susceptible to various transformations:

  • Cross-Coupling Reactions: This is arguably the most significant class of reactions for this intermediate. The bromine atoms serve as excellent electrophilic partners in palladium-catalyzed cross-coupling reactions like the Suzuki-Miyaura (with boronic acids), Stille (with organostannanes), Heck (with alkenes), and Sonogashira (with terminal alkynes) couplings. These reactions are invaluable for forming new carbon-carbon bonds, enabling the construction of complex polyaromatic systems or functionalized organic molecules. Finding a reliable supplier for this intermediate is crucial for consistent results in these reactions.
  • Grignard Reagent Formation: Under appropriate conditions, one or both bromine atoms can be converted into Grignard reagents (e.g., via reaction with magnesium). These organometallic species are highly nucleophilic and can react with a wide range of electrophiles, such as aldehydes, ketones, esters, and epoxides, to form new carbon-carbon bonds.
  • Lithiation: Treatment with strong organolithium bases (like n-butyllithium) can lead to halogen-lithium exchange, generating organolithium species that are also potent nucleophiles.
  • Nucleophilic Aromatic Substitution (SNAr): While less common for simple aryl bromides without strong electron-withdrawing groups, under forcing conditions or with specific activating groups, nucleophilic substitution of the bromine atoms might be achievable.

The distinct ortho-dibromo substitution pattern, coupled with the tert-butyl group, offers synthetic chemists precise control over where new substituents are introduced. This makes 1,2-Dibromo-4-tert-butylbenzene a strategic choice for synthesizing molecules with specific regiochemistry, essential in drug discovery and advanced materials development. Researchers looking to buy this chemical should consult with suppliers about batch consistency and purity to ensure predictable outcomes in their demanding syntheses.

In summary, 1,2-Dibromo-4-tert-butylbenzene is a synthetically powerful intermediate whose value lies in its versatile reactivity, particularly in modern cross-coupling methodologies. Its well-defined structure and physical properties make it a reliable tool for creating intricate molecular architectures. When sourcing this compound, engaging with experienced manufacturers and suppliers, especially those in China, ensures access to quality material and competitive pricing, facilitating innovation across various chemical disciplines.