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9-Bromoanthracene

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9-Bromoanthracene Basic information
9-Bromoanthracene Chemical Properties
  • Melting point:97-100 °C(lit.)
  • Boiling point:303.85°C (rough estimate)
  • Density 1.4251 (rough estimate)
  • refractive index 1.6404 (estimate)
  • storage temp.  0-6°C
  • form Powder
  • color Yellow
  • Water Solubility Insoluble in water.
  • BRN 1869747
  • InChIKeyZIRVQSRSPDUEOJ-UHFFFAOYSA-N
  • CAS DataBase Reference1564-64-3(CAS DataBase Reference)
  • NIST Chemistry Reference9-Bromoanthracene(1564-64-3)
Safety Information
  • Hazard Codes Xi
  • Safety Statements 22-24/25
  • WGK Germany 3
  • Hazard Note Irritant
  • HS Code 29049090
MSDS
9-Bromoanthracene Usage And Synthesis
  • Description9-bromoanthracene is a kind of bromine-derived anthracene. It is known to be able to reversibly photodimerize in a head-to tail fashion upon irradiation by long-wavelength ultraviolet light. The photodimers of 9-bromoanthracene are suitable to be used as alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions. It is also used as the intermediate for the preparation of the 9-substitued form of the polycyclic aromatic hydrocarbon (PAH) anthracene.
  • Chemical Propertieswhite to light yellow crystal powder
  • PreparationAnthracene (5 g, 28.05 mmol) was dissolved in CHCl3. Then N-bromosuccinimide (NBS,4.99 g, 28.05 mmol) was added in batches away from light, and the reaction solution was continuously stirred for 12 h. The resulting mixture was stirred for another 30 min with appropriate water, and extracted with CH2Cl2. The CH2Cl2 solution was dried over anhydrous MgSO4. After removing CH2Cl2 solvent, the residue was recrystallized from anhydrous ethanol to give 4.78 g (66.3 %) of a green-yellow needle solid. 1H NMR (500 MHz, CDCl3) δ 8.55 (d, J = 8.9 Hz, 2H), 8.48 (s, 1H), 8.03 (d, J = 8.4 Hz, 2H), 7.67 – 7.60 (m, 2H), 7.56 – 7.51 (m, 2H). EI-MS (m/z): Calculated for C14H9Br: 257.13. Found [M+ ]: 255.96.
    preparation of 9-bromoanthracene
    Synthesis of 9-bromoanthracene
  • Synthesis Reference(s)The Journal of Organic Chemistry, 57, p. 2740, 1992 DOI: 10.1021/jo00035a038
  • Purification MethodsCrystallise 9-bromoanthracene from MeOH or EtOH followed by sublimation in vacuo. [Masnori et al. J Am Chem Soc 108 126 1986, Beilstein 5 IV 2295.]
  • ReferencesCohen, Nicole A., et al. Macromolecular Chemistry and Physics 210.3 ‐4 (2009): 263-268.
    Xu, Xiaoming, Wenzhe Lu, and Richard B. Cole. Analytical chemistry 68.23 (1996): 4244-4253.
    Dang, Hung, and Miguel A. Garcia-Garibay. Journal of the American Chemical Society 123.2 (2001): 355-356.
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