(1Z,4Z)-2,6-bis({2-[bis(2-methylphenyl)phosphanyl]phenyl}methyl)-4,8-dimethyl-1λ4,3,5λ4,7-tetraoxa-2,6-dipalladacycloocta-1(8),4-diene-1,5-bis(ylium)-2,6-diuide

• ChemBase ID: 302472
• Molecular Formular: C46H46O4P2Pd2
• Molecular Mass: 937.642562
• Monoisotopic Mass: 936.09410521
• SMILES: Cc1ccccc1P(c1ccccc1C[Pd-]1OC(=[O+][Pd-](OC(=[O+]1)C)Cc1ccccc1P(c1ccccc1C)c1ccccc1C)C)c1ccccc1C
• Canonical SMILES: Cc1ccccc1P(c1ccccc1C)c1ccccc1C[Pd-]1OC(=[O+][Pd-](OC(=[O+]1)C)Cc1ccccc1P(c1ccccc1C)c1ccccc1C)C
• InChI: InChI=1S/2C21H20P.2C2H4O2.2Pd/c2*1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;2*1-2(3)4;;/h2*4-15H,1H2,2-3H3;2*1H3,(H,3,4);;/q;;;;2*+1/p-2
• InChIKey: YRGPDGDJUOTURS-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (1Z,4Z)-2,6-bis({2-[bis(2-methylphenyl)phosphanyl]phenyl}methyl)-4,8-dimethyl-1λ^4,3,5λ^4,7-tetraoxa-2,6-dipalladacycloocta-1(8),4-diene-1,5-bis(ylium)-2,6-diuide
• IUPAC Traditional name: (1Z,4Z)-2,6-bis({2-[bis(2-methylphenyl)phosphanyl]phenyl}methyl)-4,8-dimethyl-1λ^4,3,5λ^4,7-tetraoxa-2,6-dipalladacycloocta-1(8),4-diene-1,5-bis(ylium)-2,6-diuide
• Synonyms: Herrmann's Catalyst; trans-Di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II); 反式二-(m)-双[2-(二邻甲苯基膦)苄基]乙酸二钯(II)

Database IDs

• CAS Number: 172418-32-5
• MDL Number: MFCD01075746

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 9.714
• LogD (pH = 7.4): 9.714
• Log P: 9.714
• Molar Refractivity: 239.0214 cm^3
• Polarizability: 92.98852 Å^3
• Polar Surface Area: 86.74 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: ca 230°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 94%

REFERENCES

• 'Palladacycle' catalyst, developed by W. A. Herrmann et al, which has been reported to surpass all previously known catalysts in the Heck coupling of aryl halides with olefins, with turnover numbers of up to 200,000: Angew. Chem. Int. Ed., 34, 1844 (1995); DE 4,421,730 (1995 to Hoechst A.-G.); Tetrahedron Lett., 37, 6535 (1996). Also highly effective in the Suzuki coupling of arylboronic acids with aryl halides (see Appendix 5), with turnover numbers up to 74,000: Angew. Chem. Int. Ed., 34, 1848 (1995); EP 690,046 (1996 to Hoechst A.-G.). Superior catalyst for anion-accelerated intramolecular coupling of phenols with aryl halides: J. Org. Chem., 62, 2 (1997):
  
• Catalyst for the first reported Pd catalyzed amination of an aryl chloride: Tetrahedron Lett., 38, 2073 (1997).
• For use in the Heck reaction in quaternary salt ionic liquids, see: J. Organomet. Chem., 572, 141 (1999).
• For a review of palladacycles as reactive intermediates, see: Chem. Ber./ Recl., 130, 1567 (1997). For a brief review of applications of the catalyst, see: Synlett, 878 (2001).