4068-76-2

Usage

Uses

Used in Scientific Research:
Methyl 5-Bromosalicylate is used as a research chemical for various scientific studies and experiments. Its unique properties and reactivity make it a valuable tool in the development of new compounds and understanding chemical reactions.
Used in Manufacturing Industries:
Methyl 5-Bromosalicylate is used as an intermediate in the production of various chemical products. Its role in organic synthesis processes allows for the creation of a wide range of compounds, contributing to the manufacturing of different products.
Used in Organic Synthesis:
Methyl 5-Bromosalicylate is used as a key intermediate in organic synthesis processes. Its reactivity and properties enable the formation of new compounds, which can be further utilized in various applications across different industries.

InChI:InChI=1/C8H7BrO3/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4,10H,1H3

Upstream product

• 67-56-1 methanol 
• 89-55-4 5-bromosalicyclic acid 
• 7726-95-6 bromine 
• 119-36-8 methyl salicylate 
• 69-72-7 salicylic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 55232-59-2 3',5',5-tribromo-2,2'-dihydroxy-3-(methoxycarbonyl)diphenylmethane 
• 55232-56-9 5-bromo-3-(3,5-dibromo-4-hydroxy-benzyl)-2-hydroxy-benzoic acid methyl ester 
• 5798-94-7 5-bromo-N,2-dihydroxybenzamide 
• 89-55-4 5-bromosalicyclic acid 
• 39635-10-4 2-hydroxy-5-bromobenzohydrazide 
• 76478-30-3 2-acetoxy-5-bromobenzoic acid methyl ester 
• 773873-65-7 methyl 5-bromo-2-ethoxybenzoate 
• 60783-90-6 5-bromo-2-ethoxy-benzoic acid 
• 60783-91-7 5-bromo-2-propoxy-benzoic acid 
• 54808-59-2 5-bromo-N-methylsalicylamide 
• 62176-16-3 5-bromo-2-isopropoxy-benzoic acid 
• 412339-87-8 5-bromo-2-phenylacetoxy-benzoic acid methyl ester 
• 7120-41-4 methyl 5-bromo-2-methoxybenzoate 
• 2476-35-9 5-bromo-2-methoxybenzoic acid 

Relevant academic research and scientific papers

Design and synthesis of benzofuro[3,2-b]pyridin-2(1H)-one derivatives as anti-leukemia agents by inhibiting Btk and PI3Kδ

Btk inhibitors and PI3Kδ inhibitors play crucial roles in the treatment of leukemia, and studies confirmed that the synergetic inhibition against Btk and PI3Kδ could gain an optimal response. Herein, a series of novel benzofuro[3,2-b]pyridin-2(1H)-one derivatives were designed and synthesized as dual Btk/PI3Kδ kinases inhibitors for the treatment of leukemia. Studies indicated that most compounds could suppress the proliferation of multiple leukemia or lymphoma cells (Raji, HL60 and K562 cells) at low micromolar concentrations in vitro. Further kinase assays identified several compounds could simultaneously inhibit Btk kinase and PI3Kδ kinase. Thereinto, compound 16b exhibited the best inhibitory activity (Btk: IC50 = 139 nM; PI3Kδ: IC50 = 275 nM) and showed some selectivity against PI3Kδ compared to PI3Kβ/γ. Finally, the SAR of target compounds was preliminarily discussed combined with docking results. In brief, 16b possessed of the potency for the further optimization as anti-leukemia drugs by inhibiting simultaneously Btk kinase and PI3Kδ kinase.

Transition-metal-based (Co2+, Ni2+and Cd2+) coordination polymers constructed by a polytopic ligand integrating both flexible aliphatic and rigid aromatic carboxylate groups: Aqueous detection of nitroaromatics

Three transition-metal-based coordination polymers (1: Co2+; 2: Ni2+and 3: Cd2+) have been solvothermally synthesized from a newly designed polytopic ligand of 4-(carboxymethoxy)-[1,1′-biphenyl]-3,4′-dicarboxylic acid (H3Lws) that integrates both flexible aliphatic and rigid aromatic carboxylate groups. In 1, each H3Lwsligand connects two Co2+ions in the partially deprotonated form of HLws2?, whereas the H3Lwsligands in 2 and 3 are fully deprotonated (Lws3?), each linking three Ni2+ions and seven Cd2+ions, respectively. Compound 1 shows a one-dimensional chain structure, and compound 2 is composed of a two-dimensional waved sheet based on Ni4(μ3-OH)2(μ2-O)4cluster. Compound 3 has a three-dimensional network structure that is constructed of two-dimensional Cd/O-based layers pillared by Lws3?spacers. Compounds 1–3 exhibit both thermal stability (>340?°C) and hydrolytic robustness even under the heating condition. In particular, compound 3 displays the strongest luminescence in aqueous solution, which is almost 2.5-fold greater than that in organic solvents. More importantly, it is proved that compound 3 can serve as a highly sensitive luminescent sensor for aqueous detection of those nitro phenolic aromatics.

Multigram Synthesis of Tetrasubsituted Dihydrobenzofuran GSK973 Enabled by High-Throughput Experimentation and a Claisen Rearrangement in Flow

This article describes two routes toward the synthesis of cis or trans C2,3,5,7-tetrasubstituted dihydrobenzofurans as potent and selective bromodomain and extra-terminal BD2 inhibitors, followed by the optimization of the synthesis of the lead molecule GSK973 to support pre-clinical efficacy and safety studies. The use of flow chemistry for a Claisen rearrangement, extensive optimization of the fluorination step, and high-yielding aminocarbonylation were key to generate the required 50 g of material. The identified new route also represents a robust starting point for further optimization.

METHODS OF TREATING CREATINE TRANSPORTER DEFICIENCY

Disclosed are methods of treating creatine transporter deficiency, comprising administering to a mammal in need thereof a therapeutically effective amount of a compound that increases transport of a substrate by a mutant or wild-type creatine transporter. Also disclosed are methods of increasing transport of guanidinoacetic acid or a salt thereof across the blood-brain barrier of a mammal, and methods of decreasing accumulation or the concentration of guanidinoacetic acid or a salt thereof in a mammalian cell.

SMALL MOLECULES TARGETING MUTANT MAMMALIAN PROTEINS

Disclosed are compounds, compositions, and methods useful for treating or preventing a disease or disorder associated with a mutation in a protein.

Synthesis, structure and in vitro cytotoxicity testing of some 2-aroylbenzofuran-3-ols

Five 2-aroyl-5-bromobenzo[b]furan-3-ol compounds (two of which are new) and four new 2-aroyl-5-iodobenzo[b]furan-3-ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and 1H NMR and 13C NMR spectroscopy. Single-crystal X-ray diffraction studies of four compounds, namely, (5-bromo-3-hydroxybenzofuran-2-yl)(4-fluorophenyl)methanone, C15H8BrFO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-chlorophenyl)methanone, C15H8BrClO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone, C15H8Br2O3, and (4-bromophenyl)(3-hydroxy-5-iodobenzofuran-2-yl)methanone, C15H8BrIO3, were also carried out. The compounds were tested for their in vitro cytotoxicity on the four human cancer cell lines KB, Hep-G2, Lu-1 and MCF7. Six compounds show good inhibiting abilities on Hep-G2 cells, with IC50 values of 1.39-8.03?μM.

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Molecular Insight into Fluorocarbon Adsorption in Pore Expanded Metal-Organic Framework Analogs

The rapid growth in the global energy demand for space cooling requires the development of more efficient environmental chillers for which adsorption-based cooling systems can be utilized. Here, in this contribution, we explore sorbents for chiller use via a pore-engineering concept to construct analogs of the 1-dimensional pore metal-organic framework MOF-74 by using elongated organic linkers and stereochemistry control. The prepared pore-engineered MOFs show remarkable equilibrium adsorption of the selected fluorocarbon refrigerant that is translated to a modeled adsorption-based refrigeration cycle. To probe molecular level interactions at the origin of these unique adsorption properties for this series of Ni-MOFs, we combined in situ synchrotron X-ray powder diffraction, neutron powder diffraction, X-ray absorption spectroscopy, calorimetry, Fourier transform infrared techniques, and molecular simulations. Our results reveal the coordination of fluorine (of CH2F in R134a) to the nickel(II) open metal centers at low pressures for each Ni-MOF analog and provide insight into the pore filling mechanism for the full range of the adsorption isotherms. The newly designed Ni-TPM demonstrates exceptional R134a adsorption uptake compared to its parent microporous Ni-MOF-74 due to larger engineered pore size/volume. The application of this adsorption performance toward established chiller conditions yields a working capacity increase for Ni-TPM of about 400% from that of Ni-MOF-74, which combined with kinetics directly correlates to both a higher coefficient of performance and a higher average cooling capacity generated in a modeled chiller.

Synthesis and biological evaluation of novel 5,6,7-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents

5,6,7-Trimethoxy flavonoid salicylate derivatives were designed by the joining of three important pharmacophores (TMP, flavonoid, and SA) according to the combination principle. A series of novel trimethoxy flavonoid salicylate derivatives were synthesized and their in vitro anti-tumor activities were evaluated. Among these derivatives, compound 7f exhibited excellent antiproliferative activity against HGC-27 cells and MGC-803 cells with IC50 values of 10.26 ± 6.94 μM and 17.17 ± 3.03 μM, respectively. Subsequently, the effects on cell colony formation (clonogenic survival assay), cell migration (wound healing assay), cell cycle distribution (PI staining assay), cell apoptosis (Hoechst 33258 staining assay and annexin V-FITC/PI dual staining assay), lactate level (lactate measurement), microtubules disarrangement (immunofluorescence staining analysis) and docking posture (molecular docking simulation) were determined. Further western blot analysis confirmed that compound 7f could effectively down-regulate the expression of glycolysis-related proteins HIF-1α, PFKM and PKM2 and tumor angiogenesis-related proteins VEGF. Overall, these studies suggested that compound 7f, as the representative compound of those, might be a promising candidate for the treatment of gastric cancer and deserved the further studies.

APOPTOSIS SIGNAL-REGULATING KINASE INHIBITORS AND USES THEREOF

Described herein are ASK1 inhibitors and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of blood disease, autoimmune disorders, pulmonary disorders, hypertension, inflammatory diseases, fibrotic diseases, diabetes, diabetic nephropathy, renal diseases, respiratory diseases, cardiovascular diseases, acute lung injuries, acute or chronic liver diseases, and neurodegenerative diseases.