113931-91-2

Basic information

• Product Name: Benzeneethanol, a-(3-hydroxy-4-methoxyphenyl)-3,4,5-trimethoxy-
• Synonyms: (?à)-Isocombretastatin; (?à)-Isocombretastatin A;Isocombretastatin A
• CAS NO: 113931-91-2
• Molecular Formula: C18H22 O6
• Molecular Weight: 334.36368
• Mol File: 113931-91-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzeneethanol, a-(3-hydroxy-4-methoxyphenyl)-3,4,5-trimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, a-(3-hydroxy-4-methoxyphenyl)-3,4,5-trimethoxy-(113931-91-2)
• EPA Substance Registry System: Benzeneethanol, a-(3-hydroxy-4-methoxyphenyl)-3,4,5-trimethoxy-(113931-91-2)

Safety Data

• Hazardous Substances Data: 113931-91-2(Hazardous Substances Data)

Upstream product

• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 97315-18-9 p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde 
• 117048-66-5 1-oxo-1-(3''-hydroxy-4''-methoxyphenyl)-2-(3',4'.5'-trimethoxyphenyl)ethane 
• 956699-47-1 1-(3-(ethoxymethoxy)-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol 
• 330468-45-6 2-hydroxy-2-(3-benzyloxy-4'-methoxyphenyl)-3-(3',4',5'-trimethoxyphenyl)-propanoic acid 
• 56766-92-8 1-[4-methoxy-3-(phenylmethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)-ethanone 

Downstream Products

• 117048-66-5 1-oxo-1-(3''-hydroxy-4''-methoxyphenyl)-2-(3',4'.5'-trimethoxyphenyl)ethane 

Relevant articles and documents

Ion pairing effects on the regioselectivity of arylic versus benzylic C-O bond reductive cleavage: synthetic applications

The regioselectivity of the reductive cleavage of 3,4,5-trimethoxybenzyl methyl ether strongly depends on the alkali metal employed as a reducing agent and solvent effects. Reactions run using Na as a reducing agent led to aromatic C(4)-O bond cleavage, whilst reductions run in the presence of Na/15-crown-5, or using Li as a reducing agent, led to highly regioselective benzylic C-O bond cleavage. This regioselectivity turnaround is discussed in terms of major solvent effects affecting the fragmentation paths of a common reaction intermediate. Synthetic applications of these findings led to the synthesis of biologically active compounds, like 2,5-dialkyl-substituted resorcinols, or 1-(3,4,5-trimethoxyphenyl)-2-arylethanes structurally related to combretastatin.