tris(o-tolyl)phosphine
{{DISPLAYTITLE:Tris(o-tolyl)phosphine}}
{{Chembox
|Name = Tris(o-tolyl)phosphine
|ImageFile = P(o-tolyl)3.png
|PIN = Tris(2-methylphenyl)phosphane
|OtherNames = Tri(o-tolyl)phosphine; P(o-tol)3
|Section1={{Chembox Identifiers
|CASNo = 6163-58-2
|CASNo_Comment = hydrate
|PubChem = 80271
|ChemSpiderID = 72513
|EC_number = 228-193-9
|UNII = 5M32DK8XA8
|Beilstein = 661212
|StdInChI=1S/C21H21P/c1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3
|StdInChIKey = COIOYMYWGDAQPM-UHFFFAOYSA-N
|SMILES = CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
}}
|Section2={{Chembox Properties
|C=21|H=21|P=1
|Appearance = White solid
|MeltingPtC = 124
|MeltingPt_notes =±1
}}
|Section3={{Chembox Hazards
|GHSPictograms = {{GHS07}}{{GHS09}}
|GHSSignalWord = Warning
|HPhrases = {{H-phrases|315|319|335|410}}
|PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|391|403+233|405|501}}
}}
}}
Tris(o-tolyl)phosphine is an organophosphorus compound with the formula P(C6H4CH3)3. It is a white, water-insoluble solid that is soluble in organic solvents. In solution it slowly converts to the phosphine oxide. As a phosphine ligand, it has a wide cone angle of 194°. Consequently, it tends to cyclometalate when treated with metal halides and metal acetates. Complexes of this ligand are common in homogeneous catalysis.{{cite journal|author=Richard F. W. Jackson |author2=Manuel Perez-Gonzalez |title=Synthesis of N-(Tert-butoxycarbonyl)-β-iodoalanine Methyl Ester: A Useful Building Block in the Synthesis of Nonnatural α-amino Acids via Palladium Catalyzed Cross Coupling Reactions|journal=Org. Synth.|year=2005|volume=81|page=77|doi=10.15227/orgsyn.081.0077|doi-access=free}}
File:HerrmannCat.png, which is derived from tris(o-tolyl)phosphine.{{cite journal|author1=Herrmann, W. A. |author2=Brossmer, C. |author3=Reisinger, C.-P. |author4=Riermeier, T. H. |author5=Öfele, K. |author6=Beller, M. |title=Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides|journal=Chemistry – A European Journal|year=1997|volume=3|issue=8|pages= 1357–1364|doi=10.1002/chem.19970030823}}]]{{clear-left}}
