Tris(o-tolyl)phosphine

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.[1]

Structure of a Herrmann's catalyst, which is derived from tris(o-tolyl)phosphine.[2]

Tris(o-tolyl)phosphine

Names
IUPAC name Tris(2-methylphenyl)phosphane
Other names Tri(o-tolyl)phosphine; P(o-tol)3
Identifiers
CAS Number	6163-58-2 hydrate
3D model (JSmol)	Interactive image
Beilstein Reference	661212
ChemSpider	72513
ECHA InfoCard	100.025.631
EC Number	228-193-9
PubChem CID	80271
UNII	5M32DK8XA8
CompTox Dashboard (EPA)	DTXSID9064130
InChI InChI=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 Key: COIOYMYWGDAQPM-UHFFFAOYSA-N
SMILES CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
Properties
Chemical formula	C21H21P
Molar mass	304.373 g·mol^−1
Appearance	White solid
Melting point	124 °C (255 °F; 397 K) ±1
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335, H400, H410
GHS precautionary statements	P261, P264, P271, P273, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P391, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• Triphenylphosphine

References

1. Richard F. W. Jackson, Manuel Perez-Gonzalez (2005). "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". Org. Synth. 81: 77. doi:10.15227/orgsyn.081.0077.CS1 maint: uses authors parameter (link)
2. Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. (1997). "Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides". Chemistry – A European Journal. 3 (8): 1357–1364. doi:10.1002/chem.19970030823.CS1 maint: uses authors parameter (link)