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Usage

Uses

Used in Pharmaceutical Industry:
3'-Bromo-biphenyl-4-carbaldehyde is used as a reagent in the pharmaceutical industry for its ability to contribute to the synthesis of various organic compounds. Its chemical reactivity and aromatic nature make it a valuable building block in the development of new pharmaceuticals.
Used in Chemical Research:
In the realm of chemical research, 3'-Bromo-biphenyl-4-carbaldehyde is utilized as a reagent to explore and understand various chemical reactions and processes. Its capacity to participate in oxidation, reduction, and substitution reactions provides researchers with a tool to study and innovate within organic chemistry.
Used in Material Science:
3'-Bromo-biphenyl-4-carbaldehyde is used as a precursor in material science, where it aids in the synthesis of novel organic materials. Its potential applications in this field highlight its versatility and the breadth of its utility in creating new materials with specific properties.
Used in Organic Synthesis:
As a key component in organic synthesis, 3'-Bromo-biphenyl-4-carbaldehyde is used as a building block for the production of a variety of organic compounds. Its role in creating new chemical entities underscores its importance in advancing the field of organic chemistry and the development of new chemical products.

Upstream product

• 591-18-4 1-Bromo-3-iodobenzene 
• 87199-17-5 4-formylphenylboronic acid, 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 108-36-1 1,3-dibromobenzene 

Downstream Products

• 1413777-38-4 1-(3'-bromobiphenyl-4-yl)-N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-N-methylmethanamine 
• 566915-66-0 3-adamantan-1-yl-4-benzyloxy-[1,1';3',1'']terphenyl-4''-carboxylic acid 
• 5737-83-7 3'-bromobiphenyl-4-carboxylic acid 

Relevant academic research and scientific papers

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo

The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.

Chemical subtleties in small-molecule modulation of peptide receptor function: The case of CXCR3 biaryl-type ligands

The G protein-coupled chemokine receptor CXCR3 plays a role in numerous inflammatory events. The endogenous ligands for the chemokine receptors are peptides, but in this study we disclose small-molecule ligands that are able to activate CXCR3. A class of biaryl-type compounds that is assembled by convenient synthetic routes is described as a new class of CXCR3 agonists. Intriguingly, structure-activity relationship and structure-function relationship studies reveal that subtle chemical modifications on the outer aryl ring (e.g., either the size or position of a halogen atom) result in a full spectrum of agonist efficacies on CXCR3. Quantum mechanics calculations and nuclear Overhauser effect spectroscopy NMR studies suggest that the biaryl dihedral angle and the electronic nature of ortho-substituents play an important role in determining agonist efficacies. Compounds 38 (VUF11222) and 39 (VUF11418) are the first reported nonpeptidomimetic agonists on CXCR3, rendering them highly useful chemical tools for detailed assessment of CXCR3 activation as well as for studying downstream CXCR3 signaling.

Multi-layered, covalently supported ionic liquid phase (mlc-SILP) as highly cross-linked support for recyclable palladium catalysts for the suzuki reaction in aqueous medium

The reaction between an excess of 1,4-bis(3-vinylimidazolium-1-yl) bromide and a mercaptopropyl-modified amorphous silica gel or ordered mesoporous silica SBA-15 in the presence of azobisisobutyronitrile (AIBN) afforded new materials, which have a high loading of imidazolium moieties. These materials, which contain a highly cross-linked polymeric network, have been denoted as multi-layered, covalently supported ionic liquid phase (mlc-SILP) and have been used as support for palladium catalysts containing a high loading of the metal (10 wt%). Such materials were characterized by several techniques ( 13C magic angle spinning nuclear magnetic resonance, the Brunauer-Emmett-Teller technique, small-angle X-ray scattering, X-ray diffraction, X-ray photoelectron spectroscopy, and transmission electron microscopy). The presence of a homogeneous distribution of palladium nanoparticles was established. The palladium catalysts displayed good activity allowing the synthesis of several biphenyl compounds in high yields working with only 0.1 mol% of palladium loading at mild temperatures (room temperature or 50 °C) in ethanol/water. Reactions carried out on a 10-mmol scale required only 10 mg of catalysts. Good recyclability was observed. Copyright

Novel terphenyls and 3,5-diaryl isoxazole derivatives endowed with growth supporting and antiapoptotic properties

A new study on terphenyl and diaryl-isoxazole and -isoxazoline derivatives, maintaining a common 3-adamantyl-4-hydroxyphenyl moiety, has been conducted to find compounds with growth supporting and antiapoptotic properties. Unexpectedly, diphenyisoxazole derivatives bearing a nitro group replacing the carboxylic function have been found with the highest cell protective activity within the series, in complete and in serum-free conditions. Inhibition of apoptosis induced by daunorubicin has also been observed for the most active compound.

Studies on the apoptotic activity of natural and synthetic retinoids: Discovery of a new class of synthetic terphenyls that potently support cell growth and inhibit apoptosis in neuronal and HL-60 cells

New terphenyl derivatives have been synthesized and tested for their effect on cell survival in serum-free cultures. These compounds protected HL60 cells from death and supported their growth with an activity higher than that of the natural 14-hydroxy-retro-retinol. Terphenyls 26 and 28 also possess antiapoptotic activity on neuronal cells, proving them as possible candidates for the treatment of neurodegenerative and ischemic diseases.

A convenient synthesis of unsymmetrically substituted terphenyls of biologically active stilbenes via a double Suzuki cross-coupling protocol

A double Suzuki cross-coupling protocol has been devised as a practical route to a variety of terphenyls. Good chemoselectivity was observed. Unsymmetrically substituted triphenylenes were also easily prepared.

Efficient synthesis of porphyrin-containing, benzoquinone-terminated, rigid polyphenylene dendrimers

A series of rigid polyphenylene, free-base porphyrin-containing dendrimers terminated with either dimethoxybenzene or benzoquinone end-groups were prepared by a combined divergent and convergent synthesis. Unlike previous routes for preparing polyphenylene dendrimers that are incompatible with end-groups bearing certain functional moieties, the synthetic methodology chosen for this work enables incorporation of functional groups on the dendrimer end-groups during preparation of the dendrimer wedges and during synthesis of the final dendrimer. The basic strategy utilized a convergent preparation of dendrimer wedges using Suzuki coupling conditions, which were then either attached to a porphyrin core in a divergent coupling step or cyclized to form the porphyrin dendrimer in a convergent step. The latter approach was found to be more general and resulted in higher yields and more readily separated products. Steady-state absorption measurements for these dendrimers showed Soret and Q-band absorptions typical of free-base porphyrins. Preliminary steady-state fluorescence measurements of these dendrimers indicate quenching of the S1 state of the free-base porphyrin in all benzoquinone-containing dendrimers that is attributed to efficient electron-transfer from the excited porphyrin to the benzoquinone end-groups. The amount of fluorescence quenching was in good agreement with the number of benzoquinone groups at the dendrimer periphery and the distance between the porphyrin and benzoquinone groups as calculated by semiempirical (AM1) molecular orbital calculations.