User:Michael7604/Bis(4-bromobenzyl) ketone

{{Chembox

|Name = Bis(4-bromobenzyl) ketone

|ImageFile = 1,3-bis(4-bromophenyl)acetone structure.png

|ImageSize = 250

|ImageName = Structural formula

|ImageFile1 = 1,3-bis-4-bromophenylacetone 3d.png

|ImageSize1 = 250

|ImageName1 = Van der Waals space-filling model of Bis(4-bromobenzyl) ketone

|ImageFile2 = 1,3-bis(4-bromophenyl)acetone sample.jpg

|ImageSize2 = 120

|ImageName2 = Bis(4-bromobenzyl) ketone sample

|SystematicName = 1,3-bis(4-bromophenyl)propan-2-one

|OtherNames = 1,3-bis(4-bromophenyl)-2-propanone
1,3-bis(4-bromophenyl)acetone
4,4'-dibromodibenzyl ketone

|Section1={{Chembox Identifiers

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 10274534

|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

|InChIKey = DQQKEYDDVSREIE-UHFFFAOYSA-N

|PubChem = 12420215

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 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

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = DQQKEYDDVSREIE-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 54523-47-6

|ChEBI_Ref = {{ebicite|correct|EBI}}

|SMILES = C1=CC(=CC=C1CC(=O)CC2=CC=C(C=C2)Br)Br

}}

|Section2={{Chembox Properties

|C=15|H=12|Br=2|O=1

|MolarMass = 368.06 g/mol

}}

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.{{cite journal |last1=Bhandari |first1=Sumita |last2=Ray |first2=Suprabhat |date=17 Jun 1997 |title=A Novel Synthesis of Bisbenzyl Ketones by DCC Induced Condensation of Phenylacetic Acid |journal=Synthetic Communications |volume=28 |issue=5 |pages=765–771 |doi=10.1080/00032719808006472}}

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.{{cite journal |last1=Coan |first1=Stephen B. |last2=Trucker |first2=Donald E. |last3=Beckerr |first3=Ernest I. |date=1955 |title=The Absorption Spectra of Tetracyclones. IV |journal=Journal of the American Chemical Society |volume=77 |issue=1 |pages=60–66 |doi=10.1021/ja01606a018}} As this tetraphenylcyclopentadienone derivative may be condensed with diphenylacetylenes, this makes it a useful precursor to symmetrical hexaphenylbenzene and coronene derivatives.{{cite journal |last1=Soichi |first1=Watanabe |last2=Junji |first2=Kido |date=2007 |title=Hexaphenylbenzene Derivatives for Blue Organic Light-emitting Devices |journal=Chemistry Letters |volume=36 |issue=5 |pages=590–591 |doi=10.1246/cl.2007.590}}{{cite journal |last1=Ito |first1=Shunji |last2=Wehmeier |first2=Mike |last3=Brand |first3=J. Diedrich |last4=Kübel |first4=Christian |last5=Epsch |first5=Rebekka |last6=Rabe |first6=Jürgen P. |last7=Müllen |first7=Klaus |date=2000 |title=Synthesis and Self-Assembly of Functionalized Hexa-peri-hexabenzocoronenes |journal=Chemistry: A European Journal |volume=6 |issue=23 |pages=4327–4342 |doi=10.1002/1521-3765(20001201)6:23<4327::AID-CHEM4327>3.0.CO;2-7|pmid=11140962}}

References

:Category:Dibenzyl ketones

:Category:Bromobenzene derivatives