133932-61-3

Basic information

• Product Name: 5-BROMO-2-METHOXYRESORCINOL
• Synonyms: 5-BROMO-2-METHOXYRESORCINOL;5-BroMo-2-Methoxy-1,3-benzenediol
• CAS NO: 133932-61-3
• Molecular Formula: C₇H₇BrO₃
• Molecular Weight: 219.03
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 133932-61-3.mol

Chemical Properties

• Melting Point: 124-126°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane, Ethanol, Ethyl Acetate, Methanol
• CAS DataBase Reference: 5-BROMO-2-METHOXYRESORCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-METHOXYRESORCINOL(133932-61-3)
• EPA Substance Registry System: 5-BROMO-2-METHOXYRESORCINOL(133932-61-3)

Safety Data

• Hazardous Substances Data: 133932-61-3(Hazardous Substances Data)

Usage

Chemical Properties

Beige Crystalline Solid

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 4325, 1991 DOI: 10.1021/jo00013a052

Upstream product

• 121-43-7 Trimethyl borate 
• 607-99-8 2,4,6-tribromoanisole 

Downstream Products

• 16492-75-4 5-bromo-1,2,3 trihydroxybenzene 
• 140467-03-4 Phosphoric acid 5-bromo-2-methoxy-3-tetradecyloxy-phenyl ester 3-bromomethyl-phenyl ester 
• 58922-29-5 2,4-dihydroxy-3-methoxybenzaldehyde 
• 29267-67-2 2-methoxyresorcinol 
• 140466-83-7 5-Bromo-2-methoxy-3-tetradecyloxy-phenol 

Relevant articles and documents

TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.

An improved process for the preparation of 5-bromo-2-methoxyresorcinol

This invention is concerned with an improved process for metallating 2,4,6-tribromoanisole 1and reacting this intermediate lithio species with various electrophiles for example the trialkoxy borates which an example is trimethylborate, the improvement comprising carrying out the reaction under heterogenous conditions. This product is oxidatively converted to the compound 5-bromo-2-methoxy-resorcinol 2, which is in turn converted to the known 2-methoxy-resorcinol 3. The process and intermediate are useful in the synthesis of platelet activating factor antagonist thiazolium, 3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy) phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-, hydroxide, inner salt CA of U. S. Patent 4983592 (1991).