22717-56-2

Basic information

• Product Name: METHYL 4-BROMO-2-HYDROXYBENZOATE
• Synonyms: METHYL 4-BROMO-2-HYDROXYBENZOATE;Methyl 4-bromo-2-hydroxybenzenecarboxylate;4-Bromo-2-hydroxybenzoic acid methyl ester
• CAS NO: 22717-56-2
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• Product Categories: Aromatic Esters;Acids & Esters;Bromine Compounds;Phenols
• Mol File: 22717-56-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 41-42°
• Boiling Point: 284.7°C at 760 mmHg
• Flash Point: 126°C
• Appearance: /
• Density: 1.627g/cm³
• Vapor Pressure: 0.0017mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Room temperature.
• PKA: 8.79±0.10(Predicted)
• CAS DataBase Reference: METHYL 4-BROMO-2-HYDROXYBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-BROMO-2-HYDROXYBENZOATE(22717-56-2)
• EPA Substance Registry System: METHYL 4-BROMO-2-HYDROXYBENZOATE(22717-56-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 22717-56-2(Hazardous Substances Data)

Usage

General Description

Methyl 4-bromo-2-hydroxybenzoate is a chemical compound with the molecular formula C8H7BrO3. It is a derivative of the compound 2-hydroxybenzoic acid, also known as salicylic acid. This chemical is commonly used as an intermediate in the production of pharmaceuticals and agrochemicals. It is also used as a flavoring agent in the food industry and as an ingredient in cosmetic and personal care products. Additionally, methyl 4-bromo-2-hydroxybenzoate is used in the synthesis of various organic compounds in the laboratory. It is important to handle this chemical with care as it can be harmful if ingested, inhaled or comes into contact with skin and eyes.

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

Upstream product

• 67-56-1 methanol 
• 1666-28-0 4-bromosalicylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 65-49-6 4-Aminosalicylic acid 

Downstream Products

• 501378-89-8 4-bromo-2-dimethylthiocarbamoyloxy-benzoic acid methyl ester 
• 61799-79-9 4-bromo-2-hydroxy-benzenecarbohydroxamic acid 
• 1221891-25-3 4-bromo-2-(naphthalen-1-ylmethoxy)benzoic acid methyl ester 
• 139102-34-4 methyl 4-bromo-2-methoxybenzoate 
• 1235837-75-8 methyl 4-bromo-2-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)benzoate 
• 1312610-35-7 C₁₁H₉BrO₃ 
• 1312610-37-9 C₁₉H₁₆O₅ 
• 1312610-38-0 C₁₇H₁₂O₅ 
• 1312610-39-1 C₁₇H₁₀Cl₂O₃ 
• 1312610-40-4 C₁₉H₁₄Br₂O₃ 
• 1312610-41-5 C₄₃H₅₂N₄O₁₃ 
• 1312608-60-8 C₄₃H₅₂N₈O₇ 
• 1364266-91-0 (+/-)-methyl 4-bromo-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzoate 
• 603122-40-3 methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 

Relevant articles and documents

De Novo Design of Bioactive Small Molecules by Artificial Intelligence

Generative artificial intelligence offers a fresh view on molecular design. We present the first-time prospective application of a deep learning model for designing new druglike compounds with desired activities. For this purpose, we trained a recurrent neural network to capture the constitution of a large set of known bioactive compounds represented as SMILES strings. By transfer learning, this general model was fine-tuned on recognizing retinoid X and peroxisome proliferator-activated receptor agonists. We synthesized five top-ranking compounds designed by the generative model. Four of the compounds revealed nanomolar to low-micromolar receptor modulatory activity in cell-based assays. Apparently, the computational model intrinsically captured relevant chemical and biological knowledge without the need for explicit rules. The results of this study advocate generative artificial intelligence for prospective de novo molecular design, and demonstrate the potential of these methods for future medicinal chemistry.

Development of DHQ-based chemical biology probe to profile cellular targets for HBV

Chronic hepatitis B virus (HBV) infection has been a serious public health burden worldwide. Current anti-HBV therapies could not eliminate HBV ultimately. Considering the characteristics of HBV, it is impossible to be entirely cured based on current therapies. Therefore, it is urgently needed to develop novel therapeutic agents with new mechanism of action. The dihydroquinolizinone (DHQ) derivatives exhibited potent anti-HBV activity by decreasing HBV DNA and HBsAg level in an obscure mechanism of action. In this study, we have optimized the DHQ scaffold, developed the photoaffinity probe, with which to identify potential binding proteins.

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.