User:Michael7604/Bis(4-bromobenzyl) ketone

Bis(4-bromobenzyl) ketone
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
CAS Number	54523-47-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	10274534 ;
PubChem CID	12420215;
	InChI 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 ; 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;
	SMILES C1=CC(=CC=C1CC(=O)CC2=CC=C(C=C2)Br)Br;
Properties
Chemical formula	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

Tracking categories (test):

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

Preparation[edit]

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

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]

^ 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.
^ 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.
^ 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.
^ 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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