bis(2-{[bis(2,4-di-tert-butylphenoxy)phosphanyl]oxy}-3,5-di-tert-butylphenyl)cyclodipalladachlorane-1,3-bis(ylium)-2,4-diuide

• ChemBase ID: 134883
• Molecular Formular: C84H124Cl2O6P2Pd2
• Molecular Mass: 1575.573282
• Monoisotopic Mass: 1572.63199231
• SMILES: CC(C)(C)c1ccc(c(c1)C(C)(C)C)OP(Oc1ccc(cc1C(C)(C)C)C(C)(C)C)Oc1c(cc(cc1[Pd-]1[Cl+][Pd-]([Cl+]1)c1cc(cc(c1OP(Oc1ccc(cc1C(C)(C)C)C(C)(C)C)Oc1ccc(cc1C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C
• Canonical SMILES: CC(c1cc([Pd-]2[Cl+][Pd-]([Cl+]2)c2cc(cc(c2OP(Oc2ccc(cc2C(C)(C)C)C(C)(C)C)Oc2ccc(cc2C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)c(c(c1)C(C)(C)C)OP(Oc1ccc(cc1C(C)(C)C)C(C)(C)C)Oc1ccc(cc1C(C)(C)C)C(C)(C)C)(C)C
• InChI: InChI=1S/2C42H62O3P.2Cl.2Pd/c2*1-37(2,3)28-19-22-34(31(25-28)40(10,11)12)43-46(44-35-23-20-29(38(4,5)6)26-32(35)41(13,14)15)45-36-24-21-30(39(7,8)9)27-33(36)42(16,17)18;;;;/h2*19-23,25-27H,1-18H3;;;;/q;;2*+1;2*-1
• InChIKey: HPRPCQXYHQYGHY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2-{[bis(2,4-di-tert-butylphenoxy)phosphanyl]oxy}-3,5-di-tert-butylphenyl)cyclodipalladachlorane-1,3-bis(ylium)-2,4-diuide
• IUPAC Traditional name: bis(2-{[bis(2,4-di-tert-butylphenoxy)phosphanyl]oxy}-3,5-di-tert-butylphenyl)cyclodipalladachlorane-1,3-bis(ylium)-2,4-diuide
• Synonyms: Bedford Catalyst; Bis[2-(bis(2,4-di-tert-butylphenoxy)phosphino-κP-oxy)-3,5-di-tert-butylphenyl-κC]di-μ-chloro-dipalladium; 2-[Bis(2,4-di-tert-butyl-phenoxy)phosphinooxy]-3,5-di(tert-butyl)phenyl-palladium(II) chloride dimer; Bedford 催化剂; 双[2-(双(2,4-二-叔丁基苯氧基)膦基-κP-氧)-3,5-二-叔丁基苯基-κC]二-μ-氯-二钯; 2-[双(2,4-二-叔丁基-苯氧基)膦氧]-3,5-二(叔丁基)苯基-氯化钯(II)二聚体

Database IDs

• CAS Number: 217189-40-7
• MDL Number: MFCD05664719
• PubChem SID: 24889958; 162229159
• PubChem CID: 71308959

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 31.8086
• LogD (pH = 7.4): 31.8086
• Log P: 31.8086
• Molar Refractivity: 409.715 cm^3
• Polarizability: 168.13857 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ~12% Pd basis
• Empirical Formula (Hill Notation): C84H124Cl2O6P2Pd2

DETAILS

Sigma Aldrich - 94905

Other Notes
Very active catalyst for coupling reactions proceeding in high turnover; it shows good air and thermal stability7,8
Application
Catalyst for:
• Racemic and asymmetric sequential aldol condensations / addition reactions1
• Miyaura borylations2
• Lewis acid catalysis3
• Allylation of aldehydes4
• Addition reactions5
• Alkoxy- and amidocarbonylations6