2426-61-1

Basic information

• Product Name: 2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde
• Synonyms: 2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde;Benzaldehyde, 3-methoxy-6-nitro-2-(phenylmethoxy)-
• CAS NO: 2426-61-1
• Molecular Formula: C₁₅H₁₃NO₅
• Molecular Weight: 287.26742
• Mol File: 2426-61-1.mol

Chemical Properties

• Appearance: /
• Solubility: DCM, Ethyl Acetate, Methanol
• CAS DataBase Reference: 2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde(2426-61-1)
• EPA Substance Registry System: 2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde(2426-61-1)

Safety Data

• Hazardous Substances Data: 2426-61-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde is used as an intermediate in the synthesis of 4-Hydroxymelatonin (H944635), a metabolite of Melatonin (M215000). Melatonin is a hormone found in animals that plays a vital role in regulating the sleep-wake cycle. The compound is used for its potential therapeutic applications in treating sleep disorders and other conditions related to the circadian rhythm.
Additionally, the compound may be utilized in the development of other pharmaceutical products due to its unique chemical structure, which can be further modified to create new drugs with various therapeutic properties.
Used in Chemical Industry:
In the chemical industry, 2-Benzyloxy-3-Methoxy-6-nitrobenzaldehyde can be employed as a building block for the synthesis of a wide range of organic compounds. Its versatile structure allows for various chemical reactions, such as reduction, oxidation, and substitution, which can lead to the formation of new molecules with different applications in various fields, including materials science, agrochemicals, and specialty chemicals.
Furthermore, the compound's reactivity and functional groups make it a valuable starting material for the development of novel chemical processes and the optimization of existing ones, contributing to the advancement of the chemical industry as a whole.

Upstream product

• 100-39-0 benzyl bromide 
• 111042-36-5 2-Hydroxy-3-methoxy-6-nitrobenzaldehyde, sodium salt 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 2426-85-9 2-Hydroxy-3-methoxybenzaldehyde benzenesulfonate 
• 2426-86-0 2-hydroxy-3-methoxy-6-nitrobenzaldehyde 
• 100-44-7 benzyl chloride 

Downstream Products

• 120075-47-0 2-benzyloxy-3-methoxy-6-nitrobenzoic acid 
• 120075-75-4 C₄₈H₅₈N₈O₄ 
• 120075-76-5 C₄₄H₅₀N₆O₈ 
• 120622-50-6 3,3'-(3,6-dioxaoctamethylene)bis<8-(4-N,N-dimethylaminophenylimino)-6-methoxy-4,5-quinazolinedione> 
• 120075-74-3 C₃₈H₄₀N₆O₆ 
• 120622-47-1 3,3'-(3,6-dioxaoctamethylene)bis(5-benzyloxy-6-methoxy-4(3H)-quinazolinone) 
• 120075-73-2 N-(5-Benzyloxy-6-methoxy-quinazolin-4-yl)-N'-[3-(5-benzyloxy-6-methoxy-quinazolin-4-ylamino)-propyl]-N'-methyl-propane-1,3-diamine 
• 120075-72-1 N,N'-Bis-(5-benzyloxy-6-methoxy-quinazolin-4-yl)-heptane-1,7-diamine 
• 120075-71-0 N,N'-Bis-(5-benzyloxy-6-methoxy-quinazolin-4-yl)-ethane-1,2-diamine 
• 120075-51-6 5-(benzyloxy)-6-methoxyquinazolin-4(3H)-one 
• 120075-49-2 6-amino-2-benzyloxy-3-methoxybenzoic acid 
• 120075-53-8 5-(benzyloxy)-4-chloro-6-methoxyquinazoline 
• 880153-94-6 {(S)-1-[3-Benzyloxy-2-(2,2-dibromo-vinyl)-4-methoxy-phenylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 863870-45-5 3-benzyloxy-2-(2,2-dibromovinyl)-4-methoxy-phenylamine 

Relevant articles and documents

Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxy phenoxy)ethylamino)propan-2-ol analogs and its enantiomers. Part 2

The synthesis of (2RS)-1-(5-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol and (2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol and its enantiomers, analogs of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol ((RS)-9) is described. Compounds were tested for electrographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for α1-, α2- and β1-adrenoceptors binding affinities. The antagonist potency of the new compounds was compared with carvedilol and (RS)-9.

A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles

(Chemical Equation Presented) A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The orthogonal approach of the sequential copper- and palladium-mediated synthesis of 1,2-diarylindoles exploited the wide availability of diverse organoboron reagents.

2-SUBSTITUTED INDOLES, THEIR PRECURSORS AND NOVEL PROCESSES FOR THE PREPARATION THEREOF

Disclosed are processes for the preparation of 2-substituted indole compounds wherein the 2-substituent comprises an R4 group, wherein R4 is selected from the group consisting of monocyclic aromatic, polycyclic aromatic, monocyclic heteroaromatic, polycyclic heteroaromatic, 1° alkyl, and alkenyl, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents, and wherein R4 is bonded to the 2-position of the indole ring via a C-C bond; the process comprising reacting an ortho-gem-dihalovinylaniline compound of the formula (I): wherein Halo comprises Br, Cl, or I; each of the one or more R1 is independently selected from the group consisting of H, fluoro, lower alkyl, lower alkenyl, lower alkoxy, aryloxy, lower haloalkyl, lower alkenyl, -C(O)O-lower alkyl, monocyclic or polycyclic aryl or heteroaryl moiety, or R1 is an alkenyl group bonded so to as to form a 4- to 20-membered fused monocycle or polycyclic ring with the indole ring; all of which are optionally substituted with one or more suitable substituents at one or more substitutable positions; R2 comprises H, alkyl, cycloalkyl, aryl, heteroaryl, aryl-loweralkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; R3 comprises H, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aryl-(C1-6)alkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; with an organoboron reagent selected from the group consisting of a boronic ester of R4, a boronic acid of R4, a boronic acid anhydride of R4, a trialkylborane of R4 and a 9-BBN derivative of R4; in the presence of a base, a palladium metal pre-catalyst and a ligand under reaction conditions effective to form the 2-substituted indole compound. Also disclosed are processes for the preparation of ortho-gem-dihalovinylaniline compounds. Novel compounds prepared by the processes and novel uses of the compounds are likewise disclosed.

Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: A modular synthesis of 2-substituted indoles

(Chemical Equation Presented) 2-Substituted indoles were synthesized via a Pd-catalyzed tandem C-N/Suzuki-Miyaura coupling from readily prepared ortho-gem-dihalovinylanilines. Optimal conditions used a Pd(OAc) 2/S-Phos catalyst in the presence of K3PO 4·H2O and an organoboron reagent, which included boronic acids, esters, alkyl 9-BBN derivatives, and trialkylboranes. Yields of the desired indoles were good to excellent using low catalyst loadings (typically 1 mol %).