4433-18-5

Usage

Structure

A biphenyl derivative with four methoxy groups attached at the 2, 2', 3, and 3' positions.

Applications

a. Research and industrial applications as a building block for the synthesis of various organic compounds.
b. Pharmaceutical industry as a precursor for new drug compounds.
c. Development of new materials and polymers.

Biological activity

a. Studied for potential antioxidant properties.
b. Studied for potential anti-inflammatory properties.

Further research

Needed to fully understand its biological activity and potential uses in medicine and other fields.

Upstream product

• 4697-57-8 methyl 2-(2-bromo-4,5-dimethoxyphenyl)acetate 
• 40972-86-9 (2,3-dimethoxyphenyl)boronic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 106-95-6 allyl bromide 

Downstream Products

• 133545-19-4 (RS)-(5,5',6,6'-tetramethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) 
• 1407497-39-5 3,4,5,6-tetramethoxy-9-phenyl-10-(o-tolyl)phenanthrene 
• 19261-03-1 2,3,2',3'-Tetrahydroxy-biphenyl 
• 291782-01-9 4,4'-dimethoxy-6-N-(α-methylbenzyl)aminedibenzo-(d,f)(1,3,2)dioxaphosphepin-6-oxide 

Relevant academic research and scientific papers

Deprotonative metalation of substituted aromatics using mixed lithium-cobalt combinations

The deprotonation of anisole was attempted using different homo- and heteroleptic TMP/Bu mixed lithium-cobalt combinations. Using iodine to intercept the metalated anisole, an optimization of the reaction conditions showed that in THF at room temperature 2 equiv of base were required to suppress the formation of the corresponding 2,2′-dimer. The origin of the dimer was not identified, but its formation was favored with allyl bromide as electrophile. The metalated anisole was efficiently trapped using iodine, anisaldehyde, and chlorodiphenylphosphine, and moderately employing benzophenone, and benzoyl chloride. 1,2-, 1,3-, and 1,4-dimethoxybenzene were similarly converted regioselectively to the corresponding iodides. It was observed that 2-methoxy- and 2,6-dimethoxypyridine were more prone to dimerization than the corresponding benzenes when treated similarly. Involving ethyl benzoate in the metalation-iodination sequence showed that the method was not suitable to functionalize substrates bearing reactive functions.

The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids

We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported.