Phenanthrenequinone
Product Information
Molecular Formula
C14H8O2
Molecular Weight
208.22
Description
9,10-phenanthroquinone is a member of phenanthrenes.
Synonyms
9,10-dihydro-9,10-dioxo-phenanthren; 9,10-phenanthraquinone[qr]; 9,10-phenanthrenequinone[qr]; phenanthraquinone[qr]; Phenanthrene, 9,10-dihydro-9,10-dioxo-; phenanthrene,9,10-dihydro-9,10-dioxo-[qr]; phenanthrenequinone[qr]; Phenanthroquinone
IUPAC Name
phenanthrene-9,10-dione
SMILES
C1=CC=C2C(=C1)C3=CC=CC=C3C(=O)C2=O
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 °C / 760 mmHg
Melting Point
210 °C
Purity
98%
Density
1.405
Solubility
Solubility in water: 0.4 mg/mL
Appearance
burnt-orange powder
Application
Used in dyes, as a hardener for dental restoration, for the determination of copper by spectrophotometric method, and for organic synthesis; Used as fungicide, bactericide, and wood preservative.
Storage
Sealed in dry. Room temperature.
LogP
log Kow = 2.52
Vapor Pressure
0.00000002 [mmHg]
Henry's Law Constant
2.7X10-9 atm-cu m/mol at 25 °C (est)
Safety Information
Hazards
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
H400:
Very toxic to aquatic life.
Causes skin irritation.
H319:
Causes serious eye irritation.
H400:
Very toxic to aquatic life.
Precautionary Statement
P264:
Wash thoroughly after handling.
P273:
Avoid release to the environment.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P391:
Collect spillage.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Wash thoroughly after handling.
P273:
Avoid release to the environment.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P391:
Collect spillage.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Signal Word
Warning
Computed Properties
XLogP3
2.5
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
208.052429494 g/mol
Monoisotopic Mass
208.052429494 g/mol
Topological Polar Surface Area
34.1Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
289
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114149803-A | Method for synthesizing CdS quantum dots by water phase one-pot method and application of CdS quantum dots | 2021-12-23 |
| JP-3236461-U | Photosensitive resin composition for sandblasting | 2021-12-21 |
| JP-2022027992-A | Wiring board and its manufacturing method | 2021-12-20 |
| CN-114181156-A | Fluorescent material with on-off response to pH change of acid and alkali and application thereof | 2021-12-16 |
| JP-2022040133-A | A photosensitive coloring composition for a color filter for a solid-state image sensor, a color filter, and a solid-state image sensor using the same. | 2021-12-15 |
| CN-114031565-A | N, N' -disubstituted dihydrophenazine-based compound and preparation method and application thereof | 2021-12-09 |
| CN-114149438-A | Quinoxaline and diazole derivatives based on 9, 10-dimethyl-9, 10-ethylene anthracene and preparation method thereof | 2021-12-03 |
| CN-114114837-A | Dry film resist and preparation method thereof | 2021-11-25 |
| CN-114114842-A | Dry film resist laminate, resin composition and preparation method thereof | 2021-11-25 |
| CN-113896735-A | Thermal activation red light delay material based on coumarin-pyrazine structure and application of thermal activation red light delay material in organic electroluminescent device | 2021-11-16 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 34391839 | 2021-09-01 | 9,10-Phenanthrenequinone provokes dysfunction of brain endothelial barrier through down-regulating expression of claudin-5 | Toxicology |
| 32493877 | 2020-01-01 | Redox cycling of 9,10-phenanthrenequinone activates epidermal growth factor receptor signaling through S-oxidation of protein tyrosine phosphatase 1B | The Journal of toxicological sciences |
| 30926317 | 2019-05-25 | Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11 | Chemico-biological interactions |
| 29108775 | 2018-01-05 | Facilitation of 9,10-phenanthrenequinone-elicited neuroblastoma cell apoptosis by NAD(P)H:quinone oxidoreductase 1 | Chemico-biological interactions |
| 28595002 | 2017-07-17 | Diacetyl/l-Xylulose Reductase Mediates Chemical Redox Cycling in Lung Epithelial Cells | Chemical research in toxicology |
| 25289770 | 2015-06-05 | Protective roles of aldo-keto reductase 1B10 and autophagy against toxicity induced by p-quinone metabolites of tert-butylhydroquinone in lung cancer A549 cells | Chemico-biological interactions |
| 24813866 | 2014-07-15 | Exposure to 9,10-phenanthrenequinone accelerates malignant progression of lung cancer cells through up-regulation of aldo-keto reductase 1B10 | Toxicology and applied pharmacology |
| 24246760 | 2014-01-25 | Biochemical properties of human dehydrogenase/reductase (SDR family) member 7 | Chemico-biological interactions |
| 23684558 | 2013-09-01 | Comparative developmental toxicity of environmentally relevant oxygenated PAHs | Toxicology and applied pharmacology |
| 23261716 | 2013-02-25 | New enzymatic assay for the AKR1C enzymes | Chemico-biological interactions |
