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680990

Sigma-Aldrich

1,1′-Bis[(2R,5R)-2,5-diethylphospholano]ferrocene

Synonym(s):

R,R-Et-Ferrocelane™

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About This Item

Empirical Formula (Hill Notation):
C26H40FeP2
CAS Number:
147762-89-8
Molecular Weight:
470.39
UNSPSC Code:
12352005
PubChem Substance ID:
24885607
NACRES:
NA.22

form

solid

optical activity

[α]20/D +380°, c = 1 in chloroform

mp

85-91 °C

SMILES string

C[Fe]C.CC[C@@H]1CC[C@@H](CC)P1[C@@H]2CCCC2.CC[C@@H]3CC[C@@H](CC)P3[C@H]4CCCC4

InChI

1S/2C13H25P.2CH3.Fe/c2*1-3-11-9-10-12(4-2)14(11)13-7-5-6-8-13;;;/h2*11-13H,3-10H2,1-2H3;2*1H3;/t2*11-,12-;;;/m11.../s1

InChI key

CPUKIDAUDCWIRT-QULUYMGFSA-N

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
1,1′-Bis[(2R,5R)-2,5-diethylphospholano]ferrocene can be used:
  • As a catalyst in the asymmetric hydrogenation reactions of olefins and ketones.
  • As a component of a rhodium based precatalyst, applicable in the 2-methylenesuccinamic acid hydrogenation reaction.

Legal Information

Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.
Ferrocelane is a trademark of Kanata Chemical Technologies, Inc.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Highly efficient asymmetric hydrogenation of 2-Methylenesuccinamic acid using a Rh-DuPHOS catalyst
Cobley CJ, et al.
Organic Process Research & Development, 7(3), 407-411 (2003)
New chiral 1, 1′-bis (phospholano) ferrocene ligands for asymmetric catalysis
Burk MJ and Gross MF
Tetrahedron Letters, 35(50), 9363-9366 (1994)

Articles

DuPhos and BPE Ligands

Asymmetric hydrogenation enables scalable synthesis of single-enantiomer compounds with minimal byproducts, ideal for commercial manufacturing.

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