| Identification | More | [Name]
9,10-Dibromoanthracene | [CAS]
523-27-3 | [Synonyms]
9,10-DIBROMOANTHRACENE
9,10-DIRBOMOANTHRACENE
9,10-dibromoananthracene
9,10-dibromo-anthracen
Anthracene,9,10-dibromo-
ms-Dibromoanthracene
9,1O-dibromoanthracene
9,10-Dibromoanthracene99%
9,I O-Dibromanthracen
9,10-DIBROMO ANTHRACENEN | [EINECS(EC#)]
208-342-4 | [Molecular Formula]
C14H8Br2 | [MDL Number]
MFCD00001244 | [Molecular Weight]
336.02 | [MOL File]
523-27-3.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S60:This material and/or its container must be disposed of as hazardous waste .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3077 | [WGK Germany ]
3 | [TSCA ]
Yes | [HS Code ]
29039990 |
| Hazard Information | Back Directory | [Description]
9,10-Dibromoanthracene is an organic chemical compound containing anthracene with two bromine atoms substituted on its central ring. As a symmetrically brominated anthracene derivative, it is bearing functional groups to extend its conjugation further mainly via C-C bond forming i.e. Stille and Suzuki coupling reactions. It is notable in that it was the first single molecule to have a chemical reaction observed by an atomic force microscope and scanning tunneling microscopy. It is a low-molecular-weight organic semiconductor. It can used as an initiator in visible-spectrum solar-light-mediated benzylic C–H oxygenation through solar light or the blue LED activate[1-2]. | [Chemical Properties]
Yellow to yellow-green fluffy powder | [Uses]
9,10-Dibromoanthracene is a dibrominated polycyclic aromatic hydrocarbon (PAH). 9,10-Dibromoanthracene is often used as an energy acceptor and activator in reactions that produce chemiluminescence. | [Preparation]
9,10-Dibromoanthracene is synthesized by the bromination of anthracene. The bromination reaction is carried out at room temperature using carbon tetrachloride as a solvent. Using 80-85% anthracene as raw material, adding bromine to react for half an hour, the yield is 83-88%. | [Origin]
9,10-Dibromoanthracene was first synthesized in 1923 by Ian (formerly Isidor) M. Heilbron and John S. Heaton, chemists working at the University of Liverpool.
| [Purification Methods]
Recrystallise it from toluene, xylene or CCl4 (yellow needles), and sublime it in a vacuum [Johnston et al. J Am Chem Soc 109 1291 1987]. [Heilbron & Heaton Org Synth Coll Vol I 207 1941, Beilstein 5 H 665.] | [References]
[1] Santra S, et al. Visible-Spectrum Solar-Light-Mediated Benzylic C–H Oxygenation Using 9,10-Dibromoanthracene As an Initiator. The Journal of Organic Chemistry, 2020; 86: 1164–1171.
[2] Watanabe M. Formation of aligned needle-like crystals of 9,10-dibromoanthracene in small droplets. Journal of Applied Polymer Science, 2023; 140: e54515.
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