Bis(4-bromobenzyl) ketone
Structural formula
Van der Waals space-filling model of Bis(4-bromobenzyl) ketone
Bis(4-bromobenzyl) ketone sample
Names
Systematic IUPAC name
1,3-bis(4-bromophenyl)propan-2-one
Other names
1,3-bis(4-bromophenyl)-2-propanone
1,3-bis(4-bromophenyl)acetone
4,4'-dibromodibenzyl ketone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C15H12Br2O/c16-13-5-1-11(2-6-13)9-15(18)10-12-3-7-14(17)8-4-12/h1-8H,9-10H2 checkY
    Key: DQQKEYDDVSREIE-UHFFFAOYSA-N checkY
  • InChI=1S/C15H12Br2O/c16-13-5-1-11(2-6-13)9-15(18)10-12-3-7-14(17)8-4-12/h1-8H,9-10H2
    Key: DQQKEYDDVSREIE-UHFFFAOYSA-N
  • C1=CC(=CC=C1CC(=O)CC2=CC=C(C=C2)Br)Br
Properties
C15H12Br2O
Molar mass 368.06 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bis(4-bromobenzyl) ketone is a variation of dibenzyl ketone containing 2 bromine atoms at the para positions of the phenyl rings.

Preparation

Bis(4-bromobenzyl) ketone may be prepared in the laboratory by ketonic decarboxylation of 4-bromophenylacetic acid using DCC and DMAP.[1]

Reactions

Bis(4-bromobenzyl) ketone reacts with benzil in the presence of base in a double aldol condensation to form 2,5-bis(4-bromophenyl)-3,4-diphenylcyclopentadienone.[2] As this tetraphenylcyclopentadienone derivative may be condensed with diphenylacetylenes, this makes it a useful precursor to symmetrical hexaphenylbenzene and coronene derivatives.[3][4]

References

  1. ↑ Bhandari, Sumita; Ray, Suprabhat (17 Jun 1997). "A Novel Synthesis of Bisbenzyl Ketones by DCC Induced Condensation of Phenylacetic Acid". Synthetic Communications. 28 (5): 765–771. doi:10.1080/00032719808006472.
  2. ↑ Coan, Stephen B.; Trucker, Donald E.; Beckerr, Ernest I. (1955). "The Absorption Spectra of Tetracyclones. IV". Journal of the American Chemical Society. 77 (1): 60–66. doi:10.1021/ja01606a018.
  3. ↑ Soichi, Watanabe; Junji, Kido (2007). "Hexaphenylbenzene Derivatives for Blue Organic Light-emitting Devices". Chemistry Letters. 36 (5): 590–591. doi:10.1246/cl.2007.590.
  4. ↑ Ito, Shunji; Wehmeier, Mike; Brand, J. Diedrich; Kübel, Christian; Epsch, Rebekka; Rabe, Jürgen P.; Müllen, Klaus (2000). "Synthesis and Self-Assembly of Functionalized Hexa-peri-hexabenzocoronenes". Chemistry: A European Journal. 6 (23): 4327–4342. doi:10.1002/1521-3765(20001201)6:23<4327::AID-CHEM4327>3.0.CO;2-7. PMID 11140962.
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