Description Uses Preparation Reactions
ChemicalBook > CAS DataBase List > Phenanthrenequinone

Phenanthrenequinone

Description Uses Preparation Reactions
Product Name
Phenanthrenequinone
CAS No.
84-11-7
Chemical Name
Phenanthrenequinone
Synonyms
Phenanthrene-9,10-dione;9,10-PHENANTHRENEQUINONE;9,10-PHENANTHRENEDIONE;9,10-PHENANTHRAQUINONE;PHENANTHRENE-9,10-QUINONE;PHENANTHRAQUINONE;9,10-phenanthroquinone;Phenanthroquinone;Phenthrenequinone;Phenanthrenquinone
CBNumber
CB6272601
Molecular Formula
C14H8O2
Formula Weight
208.21
MOL File
84-11-7.mol
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Phenanthrenequinone Property

Melting point:
209-212 °C(lit.)
Boiling point:
360 °C
Density 
1.405
refractive index 
1.5681 (estimate)
Flash point:
245 °C
storage temp. 
Store below +30°C.
solubility 
7.5mg/l
form 
Powder
color 
Orange-brownish
Water Solubility 
Insoluble in water.
Merck 
14,7213
BRN 
608838
Stability:
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
84-11-7(CAS DataBase Reference)
NIST Chemistry Reference
9,10-Phenanthroquinone(84-11-7)
EPA Substance Registry System
9,10-Phenanthrenedione (84-11-7)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25-22
RIDADR 
UN3077
WGK Germany 
3
RTECS 
SF7875000
Autoignition Temperature
630 °C DIN 51794
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29146990
Hazardous Substances Data
84-11-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 16000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

H400Very toxic to aquatic life

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.07564
Product name
9,10-Phenanthrenequinone
Purity
for synthesis
Packaging
25g
Price
$102
Updated
2024/03/01
Sigma-Aldrich
Product number
8.07564
Product name
9,10-Phenanthrenequinone
Purity
for synthesis
Packaging
100g
Price
$286
Updated
2024/03/01
Sigma-Aldrich
Product number
156507
Product name
9,10-Phenanthrenequinone
Purity
≥99%
Packaging
5g
Price
$76.9
Updated
2024/03/01
Sigma-Aldrich
Product number
156507
Product name
9,10-Phenanthrenequinone
Purity
≥99%
Packaging
25g
Price
$273
Updated
2024/03/01
TCI Chemical
Product number
P0080
Product name
9,10-Phenanthrenequinone
Purity
>99.0%(GC)
Packaging
5g
Price
$24
Updated
2024/03/01
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Phenanthrenequinone Chemical Properties,Usage,Production

Description

9,10-phenanthrenequinone (9,10-PQ) is a quinone molecule found in air pollution abundantly in the diesel exhaust particles (DEP). This compound has studied extensively and has been shown to develop cytotoxic effects both in vitro and in vivo. 9, 10-PQ has been proposed to play a critical role in the development of cytotoxicity via generation of reactive oxygen species (ROS) through redox cycling. This compound also reduces expression of glutathione (GSH), which is critical in Phase II detoxification reactions.

Uses

9,10-Phenanthrenequinon may be used for high quality passivation on silicon (100) surfaces. Quinones may serve as substrates for a variety of flavoenzymes.
The quinones of polycyclic aromatic hydrocarbons are present in abundance in all burnt organic material. On being used to passivate silicon surfaces, it reacts with the dangling bonds on the surface via a heteroatomic Diels-Alder reaction. On account of the Π-electron conjugation, the semi conducting nature of the silicon is unaffected.

Preparation

Phenanthrenequinone is obtained by the oxidation of the hydrocarbon phenanthrene C14H10. Upon reduction with sulphur dioxide, it yields phenanthrenehydroquinone which absorbs oxygen from the air forming a black quinhydrone. Upon further oxidation the phenanthrenequinone is again formed.
9,10-Phenanthrenequinone is prepared by oxidation of phenanthrene with dihydroxy phenylselenonium benzenesulfonate in boiling dioxane-water. 9-methoxyphenanthrene is obtained when the reaction is carried out in methanol.
https://www.tandfonline.com/doi/abs/10.1080/00397919708004809

Reactions

9,10-Phenanthrenequinone (PQ) reacts with ketones under FeCl3 catalysis to furnish a variety of structurally diverse furan annulated products. While the reaction of PQ with acetone and cyclopentanone furnishes furan annulated ketals, its reaction with ethyl alkyl ketones provides 3-furaldehyde annulated products. In contrast to the reaction of PQ with cyclopentanone, its reaction with cyclohexanone furnishes a tetrahydrobenzofuran annulated secondary alcohol. The reactions of PQ with cycloheptanone and cyclooctanone take a different course to provide 7,8-dihydro-6H-cyclohepta[b]furan and 6,7,8,9-tetrahydrocycloocta[b]furan annulated products, respectively. Mechanistically, the above reactions go through aldol condensation, dehydration and cyclization to form furan-phenanthrene annulated products where in each step FeCl3 catalysis is involved.

https://pubs.rsc.org/en/content/articlelanding/2012/ra/c2ra20499a

Chemical Properties

burnt-orange powder

Uses

9,10-Phenanthrenequinone is used in the formation of spirophosphoranes containing acyclic 5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl substituent.

Uses

9,10-Phenanthrenequinon may be used for high quality passivation on silicon (100) surfaces. Quinones may serve as substrates for a variety of flavoenzymes.

Definition

ChEBI: 9,10-phenanthroquinone is a member of phenanthrenes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 3472, 1987 DOI: 10.1021/jo00391a065

General Description

The quinones of polycyclic aromatic hydrocarbons are present in abundance in all burnt organic material. On being used to passivate silicon surfaces, it reacts with the dangling bonds on the surface via a heteroatomic Diels-Alder reaction. On account of the Π-electron conjugation, the semi conducting nature of the silicon is unaffected.

Safety Profile

Poison by acute intraperitoneal route. Questionable carcinogen with experimental tumorigenic data by skin contact. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise the quinone from dioxane or 95% EtOH and dry it under vacuum. [Beilstein 7 IV 2565.]

Phenanthrenequinone Preparation Products And Raw materials

Raw materials

Sodium dichromate dihydrate Chromium(VI) oxide Phenanthrene

Preparation Products

9-PHENANTHROL 9-Hydroxy-9-fluorenecarboxylic acid
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View Lastest Price from Phenanthrenequinone manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Phenanthrenequinone 84-11-7
Price
US $999.00-800.00/ton
Min. Order
1ton
Purity
99%
Supply Ability
5000
Release date
2024-08-21
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Phenanthrenequinone 84-11-7
Price
US $200.00-95.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-24
Hebei Shengyang Water Conservancy Engineering Co., Ltd.
Product
Phenanthrenequinone 84-11-7
Price
US $18.00/kg
Min. Order
1kg
Purity
99.9
Supply Ability
5000
Release date
2024-05-10

84-11-7, PhenanthrenequinoneRelated Search:

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  • 84-11-7
  • 1984-11-07
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  • C14H8O2
  • Biochemicals and Reagents