1,2,3,4-Tetraphenylnaphthalene

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477183662

| Reference =[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/149799 1,2,3,4-Tetraphenylnaphthalene] at Sigma-Aldrich

| ImageFileL1 = Tetraphenylnaphthalene.png

| ImageAltL1 = Skeletal formula

| ImageFileR1 = Tetraphenylnaphthalene-3D-balls.png

| ImageAltR1 = Ball-and-stick model

| PIN =1,2,3,4-Tetraphenylnaphthalene

| OtherNames =

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 62982

| EINECS = 623-131-0

| InChI = 1/C34H24/c1-5-15-25(16-6-1)31-29-23-13-14-24-30(29)32(26-17-7-2-8-18-26)34(28-21-11-4-12-22-28)33(31)27-19-9-3-10-20-27/h1-24H

| SMILES1 = c15ccccc1c(c2ccccc2)c(c3ccccc3)c(c4ccccc4)c5c6ccccc6

| InChIKey = UCTTYTFENYGAPP-UHFFFAOYAS

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

| StdInChI = 1S/C34H24/c1-5-15-25(16-6-1)31-29-23-13-14-24-30(29)32(26-17-7-2-8-18-26)34(28-21-11-4-12-22-28)33(31)27-19-9-3-10-20-27/h1-24H

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

| StdInChIKey = UCTTYTFENYGAPP-UHFFFAOYSA-N

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

| CASNo =751-38-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AQ533SQ362

| PubChem =69783

| SMILES =C1=CC=C(C=C1)C2=C(C(=C(C3=CC=CC=C32)C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6

}}

|Section2={{Chembox Properties

| Formula =C{{sub|34}}H{{sub|24}}

| MolarMass =432.55 g/mol

| Appearance =

| Density =

| MeltingPtC = 199 to 201

| MeltingPt_notes =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHS_ref={{cite web |title=1,2,3,4-Tetraphenylnaphthalene |url=https://pubchem.ncbi.nlm.nih.gov/compound/69783#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2021 |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

}}

}}

1,2,3,4-Tetraphenylnaphthalene is a polycyclic aromatic hydrocarbon commonly prepared in the undergraduate teaching laboratory as an introduction to the Diels-Alder reaction, in this case between benzyne, which acts as the dienophile, (generated in situ) and tetraphenylcyclopentadienone, which acts as the diene.Organic Syntheses, Coll. Vol. 5, p.1037 (1973); Vol. 46, p.107 (1966). [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV5P1037 Link] It has two crystalline forms, and therefore has two different melting points.