93127-01-6

Basic information

• Product Name: 1,5-Cyclohexadiene-1-carbonitrile, 3,4-dioxo-
• CAS NO: 93127-01-6
• Molecular Formula: C7H3NO2
• Molecular Weight: 133.106
• Mol File: 93127-01-6.mol

Chemical Properties

• CAS DataBase Reference: 1,5-Cyclohexadiene-1-carbonitrile, 3,4-dioxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Cyclohexadiene-1-carbonitrile, 3,4-dioxo-(93127-01-6)
• EPA Substance Registry System: 1,5-Cyclohexadiene-1-carbonitrile, 3,4-dioxo-(93127-01-6)

Safety Data

• Hazardous Substances Data: 93127-01-6(Hazardous Substances Data)

Upstream product

• 767-00-0 4-cyanophenol 
• 67-56-1 methanol 
• 17345-61-8 3,4-dihydroxybenzonitrile 

Downstream Products

• 17345-61-8 3,4-dihydroxybenzonitrile 

Relevant articles and documents

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.

Effects of electron-withdrawing substituents on DPPH radical scavenging reactions of protocatechuic acid and its analogues in alcoholic solvents

The DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity of protocatechuic acid (3,4-dihydroxybenzoic acid) and its related catechols was examined. Compounds possessing strong electron-withdrawing substituents showed high activity. NMR analysis of the reaction mixtures of catechols and DPPH radical in methanol showed the formation of methanol adducts. The results suggest that high radical scavenging activity of catechols in alcohol is due to a nucleophilic addition of an alcohol molecule on o-quinones, which leads to a regeneration of a catechol structure. Furthermore, the radical scavenging activity in alcohols would largely depend on the electron-withdrawing/donating substituents, since they affect the susceptibility toward nucleophilic attacks on o-quinone.