151166-78-8

Basic information

• Product Name: 2-(2-BROMO-3,4,5-TRIMETHOXYPHENYL)-1,3-DIOXOLANE
• Synonyms: 2-(2-BROMO-3,4,5-TRIMETHOXYPHENYL)-1,3-DIOXOLANE
• CAS NO: 151166-78-8
• Molecular Formula: C₁₂H₁₅BrO₅
• Molecular Weight: 319.15
• Mol File: 151166-78-8.mol

Chemical Properties

• Boiling Point: 353.9°C at 760 mmHg
• Flash Point: 144.4°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 7.08E-05mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: 2-(2-BROMO-3,4,5-TRIMETHOXYPHENYL)-1,3-DIOXOLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-BROMO-3,4,5-TRIMETHOXYPHENYL)-1,3-DIOXOLANE(151166-78-8)
• EPA Substance Registry System: 2-(2-BROMO-3,4,5-TRIMETHOXYPHENYL)-1,3-DIOXOLANE(151166-78-8)

Safety Data

• Hazardous Substances Data: 151166-78-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H15BrO5/c1-14-8-6-7(12-17-4-5-18-12)9(13)11(16-3)10(8)15-2/h6,12H,4-5H2,1-3H3

Upstream product

• 35274-53-4 2-bromo-3,4,5-tri-methoxybenzaldehyde 
• 107-21-1 ethylene glycol 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Relevant articles and documents

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Asymmetric synthesis of (S)-(-)-N-acetylcolchinol via Ullmann biaryl coupling

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CHEMICAL PROCESSES FOR THE PREPARATION OF A COLCHINOL DERIVATIVE AND INTERMEDIATES

A process for the preparation of a colchinol derivative of the Formula (I): wherein each R, which may be the same or different, is selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group and Ac is acetyl, by reduction of the corresponding enamide of formula (II): Colchinol derivatives with high enantiomeric purity are obtained by hydrogenation in the presence of a transition metal catalyst, particularly a catalyst selected from a rhodium complex, a ruthenium complex or an iridium complex. Novel compounds of formula (II'): wherein each R, which may be the same or different, is selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group, and P is hydrogen or a suitable hydroxy protecting group are also described.

CHEMICAL PROCESSES AND INTERMEDIATES

The present invention provides a process for the formation of an enamide (III) wherein each R is independently selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group, comprising the steps of reductive acylation of an oxime of formula (IX) wherein each R is independently selected from (1-6C)alkyl, benzyl and C(O)(1-6C)alkyl, or two RO groups together form a (1-4C)alkylenedioxy group, and the hydroxy group may optionally be protected by a hydroxy protecting group; and thereafter if necessary, removal of any protecting groups. Intermediates to the enamide (III) and methods for their preparation are also described.