Herrmann's catalyst

Herrmann's catalyst
Identifiers
CAS Number	172418-32-5;
3D model (JSmol)	Interactive image;
ChemSpider	10136140;
EC Number	681-425-4;
PubChem CID	15978061;
UNII	0K4FY6KS4N;
CompTox Dashboard (EPA)	DTXSID40704833 ;
	InChI InChI=1S/2C21H20P.2C2H4O2.2Pd/c21-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;21-2(3)4;;/h24-15H,1H2,2-3H3;21H3,(H,3,4);;/q2-1;;;2+2/p-2 Key: AQTSNKXEMWZOGA-UHFFFAOYSA-L;
	SMILES CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)[O-].CC(=O)[O-].[Pd+2].[Pd+2];
Properties
Chemical formula	C46H46O4P2Pd2
Molar mass	937.66 g·mol−1
Appearance	Yellow solid
Melting point	123–125 °C (253–257 °F; 396–398 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Herrmann's catalyst is an organopalladium compound that is a popular catalyst for the Heck reaction. It is a yellow air-stable solid that is soluble in organic solvents. Under conditions for catalysis, the acetate group is lost and the Pd-C bond undergoes protonolysis, giving rise to a source of "PdP(o-tol)₃".

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Preparation

Identifiers

CAS Number	172418-32-5
3D model (JSmol)	Interactive image
ChemSpider	10136140
EC Number	681-425-4
PubChem CID	15978061
UNII	0K4FY6KS4N
CompTox Dashboard (EPA)	DTXSID40704833
InChI InChI=1S/2C21H20P.2C2H4O2.2Pd/c21-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;21-2(3)4;;/h24-15H,1H2,2-3H3;21H3,(H,3,4);;/q2-1;;;2+2/p-2 Key: AQTSNKXEMWZOGA-UHFFFAOYSA-L
SMILES CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)[O-].CC(=O)[O-].[Pd+2].[Pd+2]
Properties
Chemical formula	C₄₆H₄₆O₄P₂Pd₂
Molar mass	937.66 g·mol⁻¹
Appearance	Yellow solid
Melting point	123–125 °C (253–257 °F; 396–398 K)
Hazards
GHS labelling:^[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references