9,10-Phenanthrenequinone

IUPAC Name	phenanthrene-9,10-dione
Molecular Weight	208.21
Molecular Formula	C14H8O2
Canonical SMILES	O=C1C(=O)C2=C(C=CC=C2)C2=CC=CC=C12
InChI	InChI=1S/C14H8O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H
InChI Key	YYVYAPXYZVYDHN-UHFFFAOYSA-N
Boiling Point	360.0±0.0 °C at 760 mmHg
Melting Point	209-212 °C(lit.)
Flash Point	163.1±4.4 °C
Purity	98%
Density	1.3±0.1 g/cm3
Solubility	3.60e-05 M;Solubility in water: 0.4 mg/mL;Solubility in ethanol: 1 mg/mL; solubility in ethylene glycol methyl ether: 7 mg/mL;Soluble in benzene, ether, glacial acetic acid, hot alcohol;Soluble in sulfuric acid
Appearance	Powder
Application	9,10-Phenanthrenequinone is a burnt-orange powder that serves a multitude of functional roles. It is notably utilized for high-quality passivation on silicon (100) surfaces, ensuring the protection and stabilization of this material. Additionally, as a member of the phenanthrenes, 9,10-Phenanthrenequinone is found abundantly in diesel exhaust particles, contributing to air pollution and exhibiting cytotoxic effects both in vitro and in vivo. This compound plays a significant role in cytotoxicity by generating reactive oxygen species through redox cycling, while also reducing glutathione expression, vital for detoxification. The versatile reactivity of 9,10-Phenanthrenequinone extends to its interactions with various ketones under FeCl3 catalysis, producing diverse furan-annulated products. Through processes involving aldol condensation, dehydration, and cyclization, reaction with ketones like cycloheptanone and cyclooctanone also yields complex furan structures, showcasing its utility in synthetic chemistry.
Storage	room temp
Assay	≥99%
BeilsteinREAXYS Number	608838
EC Number	201-515-5
Fluorescence	λmax=420 nm
Impurity Content	<0.1% anthraquinone
MDL Number	MFCD00001163
Packaging	5, 25 g in glass bottle
Quality Level	100
Refractive Index	1.659
Vapor Pressure	8.5X10-7 mm Hg at 25 °C (est)