72668-05-4

Upstream product

• 85-44-9 phthalic anhydride 
• 106-41-2 4-bromo-phenol 
• 95-56-7 2-hydroxybromobenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 1609021-30-8 C₂₉H₂₁F₃O₂ 
• 1609021-29-5 C₂₇H₁₉N₃O 
• 1609021-28-4 C₂₈H₂₂O₂ 
• 1609021-34-2 2-methoxy-3-(diphenylhydroxymethyl)anthracene 
• 1609021-27-3 2-hydroxy-3-(diphenylhydroxymethyl)anthracene 
• 117-77-1 2-amino-3-hydroxy-anthraquinone 

Relevant academic research and scientific papers

Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines

Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 μM. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.

Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation

Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel-Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all. CSIRO 2008.