19551-04-3

Basic information

• Product Name: 1,2-Phenanthrenediol
• CAS NO: 19551-04-3
• Molecular Formula: C14H10O2
• Mol File: 19551-04-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-Phenanthrenediol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Phenanthrenediol(19551-04-3)
• EPA Substance Registry System: 1,2-Phenanthrenediol(19551-04-3)

Safety Data

• Hazardous Substances Data: 19551-04-3(Hazardous Substances Data)

Usage

Chemical class

Dihydroxyphenanthrenes

Physical form

Colorless solid

Production method

Oxidation of phenanthrene, a polycyclic aromatic hydrocarbon found in coal tar and oil shale

Uses

Precursor in the synthesis of various pharmaceuticals and organic compounds

Potential applications

Antioxidant, degradation of environmental pollutants

Environmental and health concerns

Potential toxicity and environmental impact, ongoing research into health and environmental effects of 1,2-phenanthrenediol and its derivatives.

Upstream product

• 573-12-6 phenanthrene 1,2-quinone 

Downstream Products

• 573-12-6 phenanthrene 1,2-quinone 
• 19551-05-4 1,2-Diacetoxy-phenanthren 

Relevant articles and documents

Synthesis of the o-Quinones and Dihydro Diols of Polycyclic Aromatic Hydrocarbons from the Corresponding Phenols

Terminal-ring trans-dihydro diol metabolites have been implicated as the ultimate carcinogenic forms of polycyclic aromatic hydrocarbons.Synthesis of these dihydro diols from the related polycyclic phenols in two steps via oxidation to the corresponding o-quinones with either Fremy's salt or phenylseleninic anhydride followed by stereospecific reduction with lithium aluminum hydride is described.The non-K-region quinones and trans-dihydro diols of naphthalene, anthracene, phenanthrene, benzanthracene, benzopyrene, and 7,12-dimethylbenzanthracene are synthesized via this approach.Although poor yields (1-4percent) were previously reported for the reduction of non-K-region quinones, an improved experimental procedure has been developed which affords the trans-dihydro diols free of the isomeric cis-dihydro diols in generally good yields.Major byproducts are the corresponding hydroquinones, previously undetected, and the related tetrahydro diols.The latter are the major products of reduction of the poorly soluble quinones of benzopyrene and benzanthracene and are shown to arise through further reduction of the dihydro diols.Since the tetrahydro diols are convertible to dihydro diols and the hydroquinones are reoxidizable to quinones, good overall conversions of quinones to dihydro diols are attainable. trans-3,4-Dihydroxy-3,4-dihydro-7,12-dimethylbenzanthracene synthesized in these studies is the most potent tumorigenic hydrocarbon metabolite tested to date.