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Phenanthrenequinone

Description Uses Preparation Reactions
Phenanthrenequinone
Phenanthrenequinone structure
CAS No.
84-11-7
Chemical Name:
Phenanthrenequinone
Synonyms
84-11-7;PHENANTHRAQUINONE;Phenanthroquinone;Phenthrenequinone;Phenanthrenquinone;PHENANTHRENEQUINONE;PHENANTHRENE CHINONE;phenanthraquinone[qr];9,10-PHENANTHRENEDIONE;9,10-PHENANTHRAQUINONE
CBNumber:
CB6272601
Molecular Formula:
C14H8O2
Formula Weight:
208.21
MOL File:
84-11-7.mol

Phenanthrenequinone Properties

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)
EWG's Food Scores
1
FDA UNII
42L7BZ8H74
NIST Chemistry Reference
9,10-Phenanthroquinone(84-11-7)
EPA Substance Registry System
9,10-Phenanthrenedione (84-11-7)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS09
Signal word  Warning
Hazard statements  H315-H319-H335-H400
Precautionary statements  P261-P305+P351+P338-P264-P280i-P337+P313
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
Toxicity LD50 orally in Rabbit: > 16000 mg/kg

Phenanthrenequinone price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 156507 9,10-Phenanthrenequinone ≥99% 84-11-7 5g $62.7 2021-03-22 Buy
Sigma-Aldrich 8.07564 9,10-Phenanthrenequinone for synthesis 84-11-7 25 g $75.11 2021-03-22 Buy
Sigma-Aldrich 8.07564 9,10-Phenanthrenequinone for synthesis 84-11-7 100 g $209.97 2021-03-22 Buy
Sigma-Aldrich 156507 9,10-Phenanthrenequinone ≥99% 84-11-7 25g $223 2021-03-22 Buy
TCI Chemical P0080 9,10-Phenanthrenequinone >99.0%(GC) 84-11-7 5g $26 2021-03-22 Buy

Phenanthrenequinone Chemical Properties,Uses,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.
9,10-Phenanthrenequinone Reaction
https://pubs.rsc.org/en/content/articlelanding/2012/ra/c2ra20499a

Chemical Properties

burnt-orange powder

Synthesis Reference(s)

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

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

Preparation Products


Phenanthrenequinone Suppliers

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ATK CHEMICAL COMPANY LIMITED
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Kindchem(Nanjing)Co.,Ltd
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View Lastest Price from Phenanthrenequinone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-01-03 Phenanthrenequinone
84-11-7
US $1.00 / KG 1KG 95-99% 1ton Career Henan Chemical Co

Phenanthrenequinone Spectrum


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