Dppf

1,1'-Bis(diphenylphosphino)ferrocene

Names
IUPAC name 1,1'- bis( diphenylphosphanyl) ferrocene
Other names 1,1'- Bis( diphenylphosphino) ferrocene, 1,1'- Ferrocenediyl- bis(diphenylphosphine), Dppf, 1,1'- Ferrocenebis (diphenylphosphine)
Identifiers
CAS Number	12150-46-8 N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:30743 Y
ChemSpider	21865114 Y
ECHA InfoCard	100.167.773
PubChem CID	635956
InChI InChI=1S/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H; Y Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N Y InChI=1/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17- -13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;/q2*-1;+2 Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N InChI=1/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;/rC34H28FeP2/c1-5-13-21(14-6-1)36(22-15-7-2-8-16-22)33-29-25-26-30(33)35(25,26,29,33)27-28(35)32(35)34(35,31(27)35)37(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20,25-32H Key: HPXNTHKXCYMIJL-KDKHWAOJAX
SMILES c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2]
Properties
Chemical formula	C34H28FeP2
Molar mass	554.391
Melting point	181 to 183 °C (358 to 361 °F; 454 to 456 K)
Hazards
Main hazards	Toxic
R-phrases (outdated)	R25
S-phrases (outdated)	S28A S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

1,1'-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorus compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines such as 1,2-bis(diphenylphosphino)ethane (dppe).

This compound is commercially available. It may be prepared by treating dilithioferrocene with chlorodiphenylphosphine:

The dilithiation of ferrocene is easily achieved with n-butyllithium in the presence of TMEDA. Many related ligands can be made in this way. The Fe center is typically not involved in the behavior of the ligand.

Dppf readily forms metal complexes. The palladium derivative, (dppf)PdCl₂, which is popular for palladium-catalyzed coupling reactions, is prepared by treating dppf with the acetonitrile or benzonitrile adducts of palladium dichloride: