179107-93-8

Basic information

• Product Name: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol
• Synonyms: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol
• CAS NO: 179107-93-8
• Molecular Formula: C₁₆H₁₈BrNO₃
• Molecular Weight: 352.22302
• Mol File: 179107-93-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 503.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.435±0.06 g/cm3(Predicted)
• PKA: 8.88±0.23(Predicted)
• CAS DataBase Reference: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol(179107-93-8)
• EPA Substance Registry System: 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol(179107-93-8)

Safety Data

• Hazardous Substances Data: 179107-93-8(Hazardous Substances Data)

Usage

Description

4-Bromo-5-[[[2-(4-hydroxyphenyl)ethyl]amino]methyl]-2-methoxyphenol is an organic compound that serves as an intermediate in the synthesis of racemic Galanthamine, a drug used for the treatment of Alzheimer's disease.
Used in Pharmaceutical Industry:
4-Bromo-5-[[[2-(4-hydroxyphenyl)ethyl]amino]methyl]-2-methoxyphenol is used as a key intermediate in the synthesis of racemic Galanthamine for the treatment of Alzheimer's disease. It is involved in the preparation process with Bromomethylmethoxybromophenol and Tyramine, initiated by K3[Fe(CN)6] to achieve ring closing. 4-broMo-5-((4-hydroxyphenethylaMino)Methyl)-2-Methoxyphenol plays a crucial role in the development of medications aimed at improving cognitive function and slowing the progression of neurodegenerative diseases.

Upstream product

• 621-59-0 isovanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 2973-59-3 2-bromoisovanillin 
• 51-67-2 tyrosamine 

Downstream Products

• 188822-63-1 N-(2-bromo-5-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)methylamine 
• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 
• 510-77-0 (-)-narwedine 
• 1953-04-4 Galantamine hydrobromide 
• 122584-14-9 N-formyl-1-bromo-narwedine 
• 2973-59-3 2-bromoisovanillin 
• 51-67-2 tyrosamine 
• 13062-78-7 N-[2-(4-hydroxyphenyl)ethyl]formamide 
• 296237-44-0 N-(2-bromo-5-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)trifluoroacetamide 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 

Relevant articles and documents

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.

Processes for the preparation of derivatives of 4a, 5, 9, 10, 11, 12-hexahydro-6H-benzofuro-[3a, 3, 2-ef][2]benzazepine

The invention relates to processes for the preparation of 4a,5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine, or derivatives thereof. Furthermore, the invention also relates to the compounds formed during the preparation of 4a, 5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine.

Development of a pilot scale process for the anti-alzheimer drug (-)-galanthamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion

(-)-Galanthamine has been synthesised using an efficient nine-step procedure, which in large scale affords 12.4 (6.7-19.1)% overall yield. The process improvements and optimization of each step are described. Notable steps include (i) an oxidative phenol coupling and (ii) crystallisation-induced chiral conversion of (±)-narwedine to (-)-narwedine. This is a practical and cost-effective synthesis of (-)-galanthamine which is amenable to pilot plant scale-up to afford sufficient material for use in clinical trials.