4377-76-8

Basic information

• Product Name: 2,4-Cyclohexadien-1-one, 6-imino-
• Synonyms: o-quinoneimine;2,4-Cyclohexadien-1-one,6-imino;o-quinonimine;6-Iminocyclohexa-2,4-dienone;ortho-benzoquinone monoimine;6-Imino-2,4-cyclohexadien-1-one;o-benzoquinoneimine;iminocyclohexadienone;1,2-Benzoquinone monoimine
• CAS NO: 4377-76-8
• Molecular Formula: C6H5NO
• Molecular Weight: 107.112
• Mol File: 4377-76-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,4-Cyclohexadien-1-one, 6-imino-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Cyclohexadien-1-one, 6-imino-(4377-76-8)
• EPA Substance Registry System: 2,4-Cyclohexadien-1-one, 6-imino-(4377-76-8)

Safety Data

• Hazardous Substances Data: 4377-76-8(Hazardous Substances Data)

Upstream product

• 95-55-6 2-amino-phenol 
• 24541-44-4 2-azidophenol 

Downstream Products

• 1916-59-2 2-aminophenoxazin-3-one 

Relevant articles and documents

Matrix isolation of o-quinoid compounds - 6-imino-2,4-cyclohexadien-1-one and 1,2-diimino-3,5-cyclohexadiene

6-Imino-2,4-cyclohexadien-1-one (1b) and 1,2-diimino-3,5-cyclohexadiene (1c) were generated in high yields from o-azidophenol (5b) and o-azidoaniline (5c), respectively, by irradiation in argon matrices at 10 K or by flash vacuum pyrolysis (FVP) with subsequent trapping of the products in solid argon. The hydrogen shift in the phenylnitrenes 6 formed as primary intermediates is very rapid, and thus the nitrenes are short-lived transients even under the conditions of matrix isolation. Ring expansion to azacycloheptatetraenes was not observed. FVP produces the thermodynamically most stable E/Z isomers of the quinones as the main products. Photolysis of the matrix-isolated quinones results in photostationary equilibria of the E/Z isomers. The stereoisomers were identified by comparison of the matrix IR spectra with ab initio calculations at the RMP2-FC-6/31G(d) level of theory. VCH Verlagsgesellschaft mbH, 1996.

Kinetic characterisation of o-aminophenols and aromatic o-diamines as suicide substrates of tyrosinase

We study the suicide inactivation of tyrosinase acting on o-aminophenols and aromatic o-diamines and compare the results with those obtained for the corresponding o-diphenols. The catalytic constants follow the order aromatic o-diamines max/KmS, follows this order: o-diphenols > o-aminophenols > aromatic o-diamines.

Photochemistry of phenyl azides bearing 2-hydroxy and 2-amino groups studied by matrix-isolation spectroscopy: Generation and characterization of reactive o-quinoid compounds

Broad-band irradiation (λ > 370 nm) of 2-hydroxyphenyl azide (1) in Ar at 10 K monitored by IR resulted in the formation of at least three major products, all of which were shown to be photointerconvertible under these conditions. The two products showing