22988-31-4

Upstream product

• 118-75-2 chloranil 
• 108-95-2 phenol 

Downstream Products

• 7251-14-1 2,5-bis-aziridin-1-yl-3,6-dichloro-[1,4]benzoquinone 
• 5030-67-1 2,5-dianilino-3,6-dichloro-1,4-benzoquinone 
• 102459-09-6 phosphoric acid diethyl ester-(2,5-dichloro-4-hydroxy-3,6-diphenoxy-phenyl ester) 

Relevant academic research and scientific papers

Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles

Unique nucleophilic substitution and addition reactions of nitrogen and sulfur nucleophiles with 1,4-quinones in aqueous suspension with amines and thiols have recently been demonstrated by us.2 However, the reactivity of oxygen nucleophiles toward nucleophilic substitution compared to nitrogen and sulfur nucleophiles 'on water' is not facile. An unprecedented economical, green methodology approach using ordinary laundry detergent (LD; washing powder, 0.5 mol %, reusable)/SDS as surfactant 'in water' for nucleophilic substitution by oxygen nucleophiles in 1,4-quinones in excellent yields has been demonstrated.

Photoreactivity of some 2-alkoxy/phenoxy-3,5,6-tri-chloro/bromo-1,4-benzoquinones

We report the reaction between 2,3,5,6-tetrachloro/bromo-1,4-benzoquinones (5A/B) with deprotonated alkoholes/phenoles 7a-e to give yellow 2-alkoxy/phenoxy-3,5,6-trichloro/bromo-1,4-benzoquinones 9A/Ba-e. These reaction products are probably photodegraded yielding the corresponding 2-hydroxy-3,5,6-trichloro/bromo-1,4-benzoquinones 15A/B. The quinones 9A/B are not O-conjugated dehydrated, and the quinones 9Ba-e are not C-3-debrominated. These reactions are observed by photodegradation from 2-dialkylamino-3,5,6-trichloro/bromo-1,4-benzoquinones.