388566-82-3

Basic information

• Product Name: Phenol, 5-(2,2-dibromoethenyl)-2-methoxy-
• CAS NO: 388566-82-3
• Molecular Formula: C9H8Br2O2
• Molecular Weight: 307.969
• Mol File: 388566-82-3.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 5-(2,2-dibromoethenyl)-2-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 5-(2,2-dibromoethenyl)-2-methoxy-(388566-82-3)
• EPA Substance Registry System: Phenol, 5-(2,2-dibromoethenyl)-2-methoxy-(388566-82-3)

Safety Data

• Hazardous Substances Data: 388566-82-3(Hazardous Substances Data)

Upstream product

• 621-59-0 isovanillin 
• 558-13-4 carbon tetrabromide 
• 388566-83-4 1-(3-tert-butyldimethylsilyloxy-4-methoxyphenyl)-2,2-dibromoethene 
• 97315-18-9 p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde 

Downstream Products

• 388566-84-5 (Z)-5-(2'-bromoethenyl)-2-methoxyphenol 
• 871940-23-7 1-ethynyl-3-hydroxy-4-methoxybenzene 
• 117048-62-1 combrestatin A₄ 
• 117048-59-6 trans-combretastatin A-4 

Relevant articles and documents

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METHOXYIMINO COMPOUNDS AND FUNGICIDE COMPOSITION COMPRISING SAME

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Stereospecific syntheses of the Z-E and E-Z vinylogues of combretastatin A-4, and two B-ring related analogues, were achieved through a Suzuki-Miyaura coupling. As compared to CA4, the derivative with a phenyl moiety has shown increased potency in its abi

Materials and methods for synthesizing stilbenes

The present invention relates materials and methods for synthesizing stilbenes, and in particular to processes for the synthesis of substituted stilbenes such as combretastatin A4. The present invention relates in particular to methods which are stereoselective for either the cis or the trans isomer of the substituted stilbene, using a Perkin-type condensation of an arylacetic acid and a substituted benzaldehyde, followed by a decarboxylation reaction to produce the substituted cis-stilbenes or a Suzuki-type reaction involving a Z or E-ethenyl halide and a substituted boronic acid in the presence of a palladium catalyst to produce specifically either the Z or E-isomer of substituted stilbenes.

Novel syntheses of cis and trans isomers of combretastatin A-4

A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.