2556-04-9

Basic information

• Product Name: 4-BENZYLOXY-3-BROMO-5-METHOXY-BENZALDEHYDE
• Synonyms: Benzaldehyde,4-(benzyloxy)-3-bromo-5-methoxy- (7CI,8CI);4-(Benzyloxy)-3-bromo-5-methoxybenzaldehyde
• CAS NO: 2556-04-9
• Molecular Formula: C₁₅H₁₃BrO₃
• Molecular Weight: 321.18
• Mol File: 2556-04-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 425.5 °C at 760 mmHg
• Flash Point: 211.1 °C
• Appearance: /
• Density: 1.421 g/cm³
• Vapor Pressure: 1.9E-07mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 4-BENZYLOXY-3-BROMO-5-METHOXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-3-BROMO-5-METHOXY-BENZALDEHYDE(2556-04-9)
• EPA Substance Registry System: 4-BENZYLOXY-3-BROMO-5-METHOXY-BENZALDEHYDE(2556-04-9)

Safety Data

• Hazardous Substances Data: 2556-04-9(Hazardous Substances Data)

Usage

General Description

4-Benzyloxy-3-bromo-5-methoxy-benzaldehyde is a chemical compound used in organic synthesis and pharmaceutical research. It is a benzaldehyde derivative, featuring a benzene ring with a methoxy group at the 5 position, a bromine atom at the 3 position, and a benzyloxy group at the 4 position. 4-BENZYLOXY-3-BROMO-5-METHOXY-BENZALDEHYDE is commonly used as a building block in the synthesis of various biologically active molecules and pharmaceuticals. Its unique structure makes it an important intermediate in the production of complex organic compounds and has potential applications in medicinal chemistry for drug discovery and development.

InChI:InChI=1/C15H13BrO3/c1-18-14-8-12(9-17)7-13(16)15(14)19-10-11-5-3-2-4-6-11/h2-9H,10H2,1H3

Upstream product

• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 121-33-5 vanillin 

Downstream Products

• 35320-87-7 5-Brom-ω-nitro-3-methoxy-4-benzyloxy-styrol 
• 73022-29-4 (2-Benzyloxy-5-dimethoxymethyl-3-methoxy-phenyl)-acetic acid methyl ester 
• 362662-60-0 4-benzyloxy-3-bromo-5-methoxy-phenol 
• 332053-47-1 2-amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile 
• 1375352-49-0 2-amino-4-(4-benzyloxy-3-bromo-5-methoxy-phenyl)-4H-benzo[h]chromene-3-carbonitrile 
• 1529796-56-2 5,5'-oxybis(4-(benzyloxy)-3-methoxybenzaldehyde) 
• 64421-39-2 anhydrofusarubin 
• 62385-85-7 2,5,8-trimethoxynaphthalene-1,4-dione 

Relevant articles and documents

Design, synthesis, and activity evaluation of novel N-benzyl deoxynojirimycin derivatives for use as α-glucosidase inhibitors

To obtain α-glucosidase inhibitors with high activity, 19 NB-DNJDs (N-benzyldeoxynojirimycin derivatives) were designed and synthesized. The results indicated that the 19 NBDNJDs displayed different inhibitory activities towards α-glucosidase in vitro. Compound 18a (1- (4-hydroxy-3-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol) showed the highest activity, with an IC50 value of 0.207 ± 0.11 mM, followed by 18b (1-(3-bromo-4-hydroxy-5- methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol, IC50: 0.276 ± 0.13 mM). Both IC50 values of 18a and 18b were significantly lower than that of acarbose (IC50: 0.353 ± 0.09 mM). According to the structure-activity analysis, substitution of the benzyl and bromine groups on the benzene ring decreased the inhibition activity, while methoxy and hydroxyl group substitution increased the activity, especially with the hydroxyl group substitution. Molecular docking results showed that three hydrogen bonds were formed between compound 18a and amino acids in the active site of α- glucosidase. Additionally, an arene-arene interaction was also modelled between the phenyl ring of compound 18a and Arg 315. The three hydrogen bonds and the arene-arene interaction resulted in a low binding energy (-5.8 kcal/mol) and gave 18a a higher inhibition activity. Consequently, compound 18a is a promising candidate as a new α-glucosidase inhibitor for the treatment of type II diabetes.

The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination

Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5′-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6′, (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6′-iodo derivatives bind to TRPV1.″

Stereoselective Synthesis of the Dihydrobenzofuran Segments of the Ephedradine Alkaloids

Syntheses of dihydrobenzofuran derivatives have involved formation of phenol substituted β-hydroxy esters by an aldol reaction followed by Lewis-acid-catalysed intramolecular cyclisation as key steps; the use of chiral oxazolidinones in the aldol reaction has formed the basis of enantiospecific syntheses.