λ2-iron(2+) ion bis(3-(diphenylphosphanyl)cyclopenta-2,4-dien-1-ide)

• ChemBase ID: 125081
• Molecular Formular: C34H28FeP2
• Molecular Mass: 554.378642
• Monoisotopic Mass: 554.10156166
• SMILES: c1ccc(cc1)P(c1ccccc1)C1=C[CH-]C=C1.[CH-]1C=CC(=C1)P(c1ccccc1)c1ccccc1.[Fe+2]
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)C1=C[CH-]C=C1.c1ccc(cc1)P(c1ccccc1)C1=C[CH-]C=C1.[Fe+2]
• 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;/q2*-1;+2
• InChIKey: KZPYGQFFRCFCPP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^2-iron(2+) ion bis(3-(diphenylphosphanyl)cyclopenta-2,4-dien-1-ide)
• IUPAC Traditional name: λ^2-iron(2+) ion bis(3-(diphenylphosphanyl)cyclopenta-2,4-dien-1-ide)
• Synonyms: 1,1′-Bis(diphenylphosphino)ferrocene; Zirconium ionophore I; Cyclopentadienyldiphenylphosphine; 1,1'-Ferrocendiylbis(diphenylphosphine); 1,1'- Bis( diphenylphosphino) ferrocene; 1,1'- Ferrocenediyl- bis(diphenylphosphinee; Dppe; 1,1'- Ferrocenebis (diphenylphosphine); 1,1'-Bis(diphenylphosphino)ferrocene; dppf; 1,1′-Ferrocenediyl-bis(diphenylphosphine); 1,1′-Bis(diphenylphosphino)ferrocene; 1,1'-Ferrocenebis(diphenylphosphine); 1,1'-Bis(diphenylphosphino)ferrocene; 1,1′-双(二苯基膦)二茂铁; 锆离子载体 I; 1,1′-二茂铁二基-双(二苯基膦); 1,1′-双(二苯基膦)二茂铁; 1,1'-双(二-苯基膦基)二茂铁

Database IDs

• CAS Number: 12150-46-8
• EC Number: 430-420-3
• MDL Number: MFCD00001422
• PubChem SID: 24850625; 24848885; 162219431
• PubChem CID: 635956; 15182658
• CHEBI ID: 30743
• Chemspider ID: 21865114
• Wikipedia Title: 1,1'-Bis(diphenylphosphino)ferrocene

CALCULATED PROPERTIES

• Acid pKa: 13.124334
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.7805
• LogD (pH = 7.4): 3.7804992
• Log P: 5.308
• Molar Refractivity: 77.2799 cm^3
• Polarizability: 30.728716 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 181-182 °C (dec.)(lit.); 181-183 °C; 181-183 °C (dec.); ca 182°C dec.
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; Carbonylations; Ene Reaction; Heck Reaction; Negishi Coupling; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling; Tsuji-Trost Reaction

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R25
• Safety Statements: 26-37; S28A S45
• TSCA Listed: 否
• GHS Pictograms: GHS07
• Main Hazard: Toxic
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (C); 97%
• Grade: purum; Selectophore™
• Quality: function tested
• Empirical Formula (Hill Notation): C34H28FeP2

DETAILS

Sigma Aldrich - 177261

Application
Ligand used in a Pd(II)-catalyzed cross-coupling synthesis of oxazepine ring systems.1
General description
Novel functionalized furan derivatives were prepared via Pd-phosphine sequential C-C and C-O bond formation.2
Packaging
1, 10, 25 g in glass bottle

Sigma Aldrich - 14816

Other Notes
Transition metal complexes are efficient catalysts for the cross-coupling of Grignard reagents with organic halides and related compounds1,2,3

Sigma Aldrich - 68646

General description
Visit our Sensor Applications portal to learn more.
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

Toronto Research Chemicals - B430350

Commonly used coordination compound in synthesis, readily forms complexes with various metals, i.e. when reacting with the acetonitrile or benzonitrile complexes of PdCl2 it forms (dppf)PdCl2, which is a popular reagent for palladium-catalyzed coupling re

REFERENCES

• Nataro, C., et al.: J. Chem. Ed., 86, 1412 (2009)
• Hindered bidentate ligand used in, for example, the Ni-catalyzed Suzuki-type crossed coupling of arylboronic acids with aryl mesylates to give biaryls: J. Org. Chem., 60, 1060, 1066 (1995), and of thiophenolates with aryl mesylates to give unsymmetrical diaryl sulfides: J. Org. Chem., 60, 6895 (1995).