74553-29-0

Usage

Uses

Used in Chemical Synthesis:
2,5-Dibromobenzaldehyde is used as an intermediate in the chemical synthesis industry. It serves as a key component in the production of other chemicals, contributing to the formation of a diverse range of compounds with various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,5-Dibromobenzaldehyde is used as a precursor for the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic properties.
Used in Organic Chemistry Research:
2,5-Dibromobenzaldehyde is also utilized in organic chemistry research, where it is employed to study the reactivity of brominated aromatic compounds and to develop new synthetic methods and reactions.
Used in the Synthesis of 2-(2,5-Dibromo-phenyl)-[1,3]dioxolane:
2,5-Dibromobenzaldehyde is used as a reactant in the synthesis of 2-(2,5-Dibromo-phenyl)-[1,3]dioxolane, a compound that can be obtained by reacting it with Ethane-1,2-diol. The reaction is facilitated by the use of p-toluenesulfonic acid as a reagent and toluene as a solvent. This specific application demonstrates the versatility of 2,5-Dibromobenzaldehyde in creating complex molecular structures.

InChI:InChI=1/C7H4Br2O/c8-6-1-2-7(9)5(3-6)4-10/h1-4H

Upstream product

• 100-52-7 benzaldehyde 
• 75-17-2 formaldoxime 
• 615-59-8 1,4-dibromo-2-methylbenzene 
• 642091-49-4 2,5-dibromobenzyl chloride 
• 106-37-6 1.4-dibromobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 3132-99-8 m-bromobenzoic aldehyde 
• 896718-38-0 3-bromobenzaldehyde O-methyloxime 
• 147034-01-3 (2,5-dibromophenyl)methanol 
• 147033-99-6 2,5-dibromophenylmethylene diacetate 

Downstream Products

• 380607-16-9 2,5-dibromocinnamic acid 
• 147034-01-3 (2,5-dibromophenyl)methanol 
• 861928-15-6 1,4-dibromo-2-(dimethoxymethyl)benzene 
• 866240-61-1 2,5-bis-{4-[(triisopropylsilanyl)-ethynyl]-phenylethynyl}-benzaldehyde 
• 885693-79-8 2,5-bis((trimethylsilyl)ethynyl)benzaldehyde 
• 1026786-20-8 5-bromo-2-(trimethylsilylethynyl)benzaldehyde 
• 1134916-66-7 5-bromo-1-(3-methoxy-phenyl)-1H-indazole 
• 1160744-75-1 C₁₁H₁₄Br₂O₂ 
• 1129606-89-8 (Z)-1,4-dibromo-2-(2-bromovinyl)benzene 
• 142770-41-0 2-(2,5-dibromophenyl)benzo[d]thiazole 
• 1235559-75-7 5-bromo-2-cyclopropylbenzaldehyde 
• 1318795-12-8 C₁₅H₉BrO 
• 57381-43-8 2,5-dibromobenzoic acid methyl ester 
• 1318794-96-5 14-bromo-10-phenyl-15bH-isoquinolino[2,1-a]pyrrolo[2,1-c]quinoxaline 

Relevant academic research and scientific papers

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy

A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.

Diverse ortho-C(sp2)-H functionalization of benzaldehydes using transient directing groups

Pd-catalyzed C-H functionalizations promoted by transient directing groups remain largely limited to C-H arylation only. Herein, we report a diverse set of ortho-C(sp2)-H functionalizations of benzaldehyde substrates using the transient directing group strategy. Without installing any auxiliary directing group, Pd(II)-catalyzed C-H arylation, chlorination, bromination, and Ir(III)-catalyzed amidation, could be achieved on benzaldehyde substrates. The transient directing groups formed in situ via imine linkage can override other coordinating functional groups capable of directing C-H activation or catalyst poisoning, significantly expanding the scope for metal-catalyzed C-H functionalization of benzaldehydes. The utility of this approach is demonstrated through multiple applications, including late-stage diversification of a drug analogue.

A Bio-inspired Approach for Chromophore Communication: Ligand-to-Ligand and Host-to-Guest Energy Transfer in Hybrid Crystalline Scaffolds

Efficient multiple-chromophore coupling in a crystalline metal-organic scaffold was achieved by mimicking a protein system possessing 100 % energy-transfer (ET) efficiency between a green fluorescent protein variant and cytochrome b562. The two

Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration

A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.

Selective ortho -bromination of substituted benzaldoximes using Pd-catalyzed C-H activation: Application to the synthesis of substituted 2-bromobenzaldehydes

Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.

Synthesis and spectroscopy of anthracene-containing linear and 'T'-shaped π-conjugated ligands

A range of new π-conjugated ethynyl- and diethynyl-benzene ligands has been synthesised and their spectroscopic characterisation carried out, most notably via IR and 1H NMR. X-ray crystal structures were obtained for three of these ligands and

The Dual Roles of Oxodiperoxovanadate Both as a Nucleophile and an Oxidant in the Green Oxidation of Benzyl Alcohols or Benzyl Halides to Aldehydes and Ketones

One catalyst, two roles: VO(O2)2- reacts as a nucleophilic oxidant under acidic conditions towards benzyl alcohols. Altogether 15 alcohols have been oxidized, in the absence of organic solvent, in excellent yields. Benzyl halides are also oxidized by H2O 2 in water catalyzed by oxodiperoxovanadate and a phase transfer catalyst into aromatic aldehydes and ketones (see scheme). This reaction is the first green oxidation of benzyl halides.

A novel and efficient oxidation of benzyl alcohols to benzaldehydes with DMSO catalyzed by acids

Oxidation of benzyl alcohols to the corresponding aldehydes was achieved by an acid catalyzed DMSO oxidation. When the oxidation was catalyzed by HBr, no side products were detected. In most cases, the yields were excellent. The oxidation rate depends on both the nature and the position of the substituents on the aromatic rings. A tentative mechanism is proposed for the oxidation.

Synthesis, absorption and luminescence of a new series of soluble distyrylbenzenes featuring cyano substituents at the peripheral rings

The synthesis of a complete series of nine soluble distyrylbenzenes (DSBs) with two (2a-c) and four cyano groups (1a-f) attached to the peripheral aromatic rings is reported. They were prepared by the Wittig reaction and characterized by 1H and 13C NMR, FT-IR, UV/Vis, PL, EL, mass spectra, and elemental analysis. The optical properties have been studied in detail to monitor structure-luminescence relationships as a function of the position of the cyano moieties. The DSBs with cyano substituents show bathochromic shifts in their absorption spectra when compared to the parent DSB (30). The extent of this red-shift depends on electronic and steric factors. The bis(p-cyano)-substituted compound 2c exhibits a small Stokes shift and a remarkably high quantum yield of ψF = 0.6-0.8 in the solid state. All the new distyrylbenzenes show electroluminescence when employed in devices with an ITO/PcCu/DSB/Al configuration and with colors ranging from red to green.

Synthesis of 2,5-dibromobenzaldehyde and its reaction with hexylmagnesium bromide

2,5-Dibromobenzaldehyde (3) is synthesized by the oxidation of 2,5-dibromotoluene (1) via 2,5-dibromobenzylidene diacetate (2). Grignard reaction of hexylmagnesium bromide with 2 gives the normal addition product, 2,5-dibromo-α-hexylbenzyl alcohol (5) and