2973-59-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromoisovanillin is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable building block for the development of new drugs with potential applications in treating a range of medical conditions.
Used in Chemical Synthesis:
In the field of organic chemistry, 2-Bromoisovanillin is used as a key intermediate for the synthesis of various organic compounds. Its reactivity and structural features allow for the creation of a wide array of molecules with diverse applications, including those in the fragrance, flavor, and specialty chemical industries.
Used in Research and Development:
Due to its unique chemical properties, 2-Bromoisovanillin is also utilized in research and development settings. It serves as a valuable tool for scientists to study the effects of bromination on the reactivity and properties of organic molecules, as well as to explore new synthetic pathways and methodologies.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 26, p. 3113, 1978 DOI: 10.1248/cpb.26.3113

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

Upstream product

• 621-59-0 isovanillin 
• 124-41-4 sodium methylate 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 67-63-0 isopropyl alcohol 
• 139-02-6 sodium phenoxide 
• 100-51-6 benzyl alcohol 
• 108-95-2 phenol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6451-86-1 5-benzyloxy-2-bromo-4-methoxybenzaldehyde 
• 17348-67-3 1-(tert-butyldimethylsilyloxy)-2-propane 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 56517-30-7 2-bromo-5-ethoxy-4-methoxybenzaldehyde 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 

Downstream Products

• 69048-79-9 4-bromo-5-formyl-2-methoxyphenyl acetate 
• 80832-63-9 3-hydroxy-4,6-dimethoxybenzaldehyde 
• 6451-86-1 5-benzyloxy-2-bromo-4-methoxybenzaldehyde 
• 4815-99-0 2-bromo-4,5-dihydroxybenzoaldehyde 
• 188822-63-1 N-(2-bromo-5-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)methylamine 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 252186-55-3 4-bromo-2-methoxy-5-(2-nitroethenyl)phenol 
• 365572-07-2 1-bromo-2-(chloromethyl)-5-methoxy-4-(1-methylethoxy)benzene 
• 365572-06-1 2-bromo-4-methoxy-5-(1-methylethoxy)benzenemethanol 
• 380375-83-7 4-bromo-5-[[2-(4-hydroxyphenyl)ethylsulfonyl]methyl]-2-methoxyphenol 
• 380375-81-5 1-bromo-5-methoxy-4-(1-methylethoxy)-2-[[[2-[4-(1-ethylethoxy)phenyl]ethyl]thio]methyl]benzene 
• 380375-82-6 1-bromo-5-methoxy-4-(1-methylethoxy)-2-[[2-[4-(1-methylethoxy)phenyl]ethylsulfonyl]methyl]benzene 
• 685873-72-7 2-bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde 
• 1097202-13-5 6-nitro-9-(3'-hydroxy-4'-methoxy-6'-bromobenzylidene)deoxyvasicinone 

Relevant academic research and scientific papers

Exploring the formation and recognition of an important G-quadruplex in a HIF1α promoter and its transcriptional inhibition by a benzo[c]phenanthridine derivative

Four putative G-quadruplex sequences (PGSs) in the HIF1α promoter and the 5′UTR were evaluated for their G-quadruplex-forming potential using ESI-MS, CD, FRET, DMS footprinting, and a polymerase stop assay. An important G-quadruplex (S1) has been proven to inhibit HIF1α transcription by blocking AP2 binding. A benzo[c]phenanthridine derivative was found to target the S1 G-quadruplex and induce its conformational conversion from antiparallel to parallel orientation. The transcriptional suppression of HIF1α by this compound was demonstrated using western blotting, Q-RT-PCR, luciferase assay, and ChIP. Our new findings provided a novel strategy for HIF1α regulation and potential insight for cancer therapy.

Biomimetic synthesis of galantamine: Via laccase/TEMPO mediated oxidative coupling

Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.

Single-Step Dual Functionalization: One-Pot Bromination-Cross-Dehydrogenative Esterification of Hydroxy Benzaldehydes with CCl 3 Br - A Comparison with Selectfluor

Bromination of phenolic compounds without directly using molecular bromine possesses much importance. In this article an Ir III /CCl 3 Br-assisted single-step double functionalization of hydroxy benzaldehydes is reported. It involves simultaneous esterification of the aldehyde group and bromination of the aryl ring of phenolic aldehydes in one-pot. The reaction proceeds under mild conditions in the presence of 445 nm blue LED light to obtain highly functionalized bromo hydroxy benzoates in moderate to good yields. In comparison, Selectfluor as an oxidant gives only non-bromo phenolic esters.

PRODRUGS OF KALLIKREIN INHIBITORS

Disclosed are compounds of formula I, II, and III, and pharmaceutically acceptable salts thereof, which are inhibitors of kallikrein. Also provided are pharmaceutical compositions comprising such a compound, and methods involving use of the compounds and compositions in the treatment and prevention of acquired or hereditary angioedema, or other diseases and conditions characterized by aberrant kallikrein activity. (I) (II) (III)

Synthesis of 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenefrequency alcohol ester (by machine translation)

The invention provides a method for synthesizing 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenefrequency alcohol ester. In particular, the invention relates to 3, 4 - dimethoxy formaldehyde as raw materials through the bromo to obtain 3, 4 - dimethoxy - 2 - bromophenylacetic formaldehyde, then by removing methyl 5 - hydroxy - 4 - methoxy - 2 - bromophenylacetic formaldehyde, then tert-butyl diphenyl silicon to protect hydroxyl to obtain 5 - tert-butyl diphenyl siloxy - 4 - methoxy - 2 - bromophenylacetic formaldehyde, then in order to glycerol acetal protected aldehyde group, then in BuLi under the action of triisopropyl borate reaction to obtain 5 - methoxy - 4 - tert-butyl diphenyl siloxy - 2 - aldehyde group benzene boric acid, then silicon protecting group to obtain 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzene, finally with the pinacone reaction ester to obtain the target product 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenepinacone ester. The invention raw materials are easy, low cost, high yield, easy industrialization. (by machine translation)

METHOD FOR PRODUCING AMIDINE DERIVATIVES

The invention provides methods and intermediates useful in the synthesis of a compound of formula (I): or a pharmaceutically acceptable salt, solvate, ester or prodrug thereof; wherein the variables are as defined herein.

Synthetic method of 6-Bromoisovanillin

The invention discloses a synthetic method of 6-Bromoisovanillin. The method comprises the steps of taking ethyl vanillin as a starting material, and preparing the 6-Bromoisovanillin through a methylation reaction, a bromination reaction and an acid decomposition reaction in sequence. After the bromination reaction is finished, first a reacted material is neutralized by using alkali liquor, and then excessive bromine is removed by using sodium thiosulfate. The acid decomposition reaction is first performed at a relatively low temperature, and then is performed at a relatively high temperature. The method provided by the invention takes the ethyl vanillin as the starting material, so the production cost is greatly reduced relative to that of expensive isovanillin. The yield of two steps of the methylation reaction and the bromination reaction can reach more than 95 percent, and more important, the reaction yield of removing ethyl by acid decomposition can reach about 75 percent, so that the total reaction yield can reach 70 percent or more than 70 percent.

COMPOSITIONS AND USES OF AMIDINE DERIVATIVES

Use of a compound of formula (I): wherein A, X, Y, R1 and R2 as defined herein, in treating hereditary angioedema is disclosed. A composition containing the compounds, a polar organic solvent or a mixture thereof; and optionally a co-solvent, is also disclosed.

Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C.

PROCESS FOR PREPARATION OF BENZAZEPINE

This invention discloses a process for manufacture of galanthamine, which involves a stereoselective reduction step to get the desired isomer of galanthamine. The current embodiment also discusses the method for improving the chiral and chemical purity of galanthamine and galanthamine salts.