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88733

Sigma-Aldrich

(R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine

≥97%

Synonym(s):

(2R)-1-[(1R)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene (acc to CAS), Josiphos SL-J009-1

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About This Item

Empirical Formula (Hill Notation):
C32H52FeP2
CAS Number:
Molecular Weight:
554.55
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97%

form

powder

optical purity

ee: ≥99%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

functional group

phosphine

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2P(C3CCCCC3)C4CCCCC4)P(C(C)(C)C)C(C)(C)C

InChI

1S/C27H47P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h14,19-23H,8-13,15-18H2,1-7H3;1-5H;/t21-;;/m1../s1

InChI key

FFFWTQLOUUWUJJ-GHVWMZMZSA-N

General description

(R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (CyPF-tBu) is a chiral ferrocenyl diphosphine ligand.
sold in collaboration with Solvias AG

Application

It may be used as a ligand in the palladium catalyzed hetero cross-coupling between aryl bromides/aryl triflates with potassium thioacetate to form S-aryl thioacetates.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A simple, base-free preparation of S-aryl thioacetates as surrogates for aryl thiols.
van den Hoogenband A, et al.
Tetrahedron Letters, 51(52), 6877-6881 (2010)
Privileged ligands
Aldrich Chemfiles, 6(8), 12-12 null

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