363598-42-9

Basic information

• Product Name: 1,3-dibromo-2-(trimethylsilyl)benzene
• Synonyms: 1,3-dibromo-2-(trimethylsilyl)benzene
• CAS NO: 363598-42-9
• Molecular Weight: 308.088
• Mol File: 363598-42-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3-dibromo-2-(trimethylsilyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dibromo-2-(trimethylsilyl)benzene(363598-42-9)
• EPA Substance Registry System: 1,3-dibromo-2-(trimethylsilyl)benzene(363598-42-9)

Safety Data

• Hazardous Substances Data: 363598-42-9(Hazardous Substances Data)

Usage

Structure

A benzene ring with two bromine atoms at the 1st and 3rd positions and a trimethylsilyl group attached to the 2nd position.

Functional groups

Bromine atoms, trimethylsilyl group

Derivative of

Benzene

Applications

Intermediate in organic synthesis, production of pharmaceuticals and agrochemicals

Role of trimethylsilyl group

Protecting group for reactive sites on the benzene ring, allowing for controlled reactions

Role of bromine atoms

Useful reagent in various organic transformations

Versatility

Wide range of applications in organic chemistry

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 108-36-1 1,3-dibromobenzene 

Downstream Products

• 1257792-94-1 3-bromo-2-(trimethylsilyl)phenylboronic acid 
• 21739-99-1 2,3,6-tribromobenzoic acid 
• 608-21-9 1,2,3-tribromobenzene 

Relevant articles and documents

Synthesis of NBN-Type Zigzag-Edged Polycyclic Aromatic Hydrocarbons: 1,9-Diaza-9a-boraphenalene as a Structural Motif

A novel class of dibenzo-fused 1,9-diaza-9a-boraphenalenes featuring zigzag edges with a nitrogen-boron-nitrogen bonding pattern named NBN-dibenzophenalenes (NBN-DBPs) has been synthesized. Alternating nitrogen and boron atoms impart high chemical stability to these zigzag-edged polycyclic aromatic hydrocarbons (PAHs), and this motif even allows for postsynthetic modifications, as demonstrated here through electrophilic bromination and subsequent palladium-catalyzed cross-coupling reactions. Upon oxidation, as a typical example, NBN-DBP 5a was nearly quantitatively converted to σ-dimer 5a-2 through an open-shell intermediate, as indicated by UV-vis-NIR absorption spectroscopy and electron paramagnetic resonance spectroscopy corroborated by spectroscopic calculations, as well as 2D NMR spectra analyses. In situ spectroelectrochemistry was used to confirm the formation process of the dimer radical cation 5a-2?+. Finally, the developed new synthetic strategy could also be applied to obtain π-extended NBN-dibenzoheptazethrene (NBN-DBHZ), representing an efficient pathway toward NBN-doped zigzag-edged graphene nanoribbons.

Extensive halogen scrambling and buttressing effects encountered upon treatment of oligobromoarenes with bases

As a rule, tri-, tetra- and pentahaloarenes readily undergo ortho-lithiation when treated with amide-type bases. However, halogen migration occurs whenever the substrate contains three or more contiguous halogen atoms, provided that at least one of them is bromine or iodine. Dismutation and reduction processes often take place concomitantly. In this manner, a variety of organometallic intermediates may be formed, the driving force always being a decrease in basicity. When no such energy gain can be achieved, a sterically crowded substrate may just turn out to be inert; this was found to be the case with 1,5-dibromo-3-fluoro-2-(trimethylsilyl)benzene, 1,5-dibromo-3-fluoro-2,4-bis(trimethylsilyl)benzene, and 1,5-dibromo-3-fluoro-2,4-diiodobenzene. Buttressing effects are apparently strong enough to prevent expedient deprotonation of those substrates.