| Identification | Back Directory | [Name]
3,6-Dibromo-phenanthrenequinone | [CAS]
53348-05-3 | [Synonyms]
3,6-DibroMo-phenanthrenequ
6-Dibromo-phenanthrenequinone
3,6-Dibromo-9,10-phenanthrenedione
3,6-Dibromophenanthrene-9,10-dione
3,6-Dibromo-9,10-phenanthrenequinone
3,6-Dibromo-9,10-dihydrophenanthrene-9,10-dione
3,6-Dibromo-phenanthrenequinone ISO 9001：2015 REACH | [Molecular Formula]
C14H6Br2O2 | [MDL Number]
MFCD00451676 | [MOL File]
53348-05-3.mol | [Molecular Weight]
366 |
| Chemical Properties | Back Directory | [Melting point ]
291 °C | [Boiling point ]
501.0±43.0 °C(Predicted) | [density ]
1.911 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
Light yellow to Brown | [InChI]
InChI=1S/C14H6Br2O2/c15-7-1-3-9-11(5-7)12-6-8(16)2-4-10(12)14(18)13(9)17/h1-6H | [InChIKey]
WPEJBJRFPBMVGJ-UHFFFAOYSA-N | [SMILES]
C1=C2C(C3=C(C(=O)C2=O)C=CC(Br)=C3)=CC(Br)=C1 |
| Hazard Information | Back Directory | [Uses]
3,6-Dibromo-phenanthrenequinone is an organic compound containing a phenanthrenequinone skeleton, and its molecule contains two bromine atoms. Due to the presence of bromine atoms, 3,6-dibromophenanthrenequinone has a higher electron density and better reactivity, making it have a high application value in organic synthesis. In addition, it is widely used in the preparation of organic electronic devices, solar cells, and optoelectronic materials.
| [Synthesis]
The general procedure for the synthesis of 3,6-dibromo-9,10-phenanthrenequinone from 9,10-phenanthrenequinone was as follows: 9,10-phenanthrenequinone (50 g), benzoyl peroxide (2.5 g), and nitrobenzene (250 mL) were added to a nitrogen-displaced reaction vessel and aerated with nitrogen. Subsequently, bromine (83 g) was added and the mixture was heated to reflux and stirred for 2 hours. Upon completion of the reaction, the mixture was allowed to cool to room temperature and ethanol (250 mL) was added to precipitate the product. The precipitated solid was collected by filtration, washed with ethanol and finally dried under vacuum to give 3,6-dibromo-9,10-phenanthrenequinone as a yellow solid in 70% yield. | [References]
[1] Journal of the American Chemical Society, 2004, vol. 126, # 19, p. 6035 - 6042
[2] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4383 - 4390
[3] Patent: WO2005/123754, 2005, A2. Location in patent: Page/Page column 50-51; Sheet 28
[4] Chemistry - A European Journal, 2014, vol. 20, # 32, p. 10170 - 10178
[5] Journal of the American Chemical Society, 2014, vol. 136, # 1, p. 427 - 435 |
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