Skip to Content
Merck
CN

698407

1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate

Synonym(s):

(S,S)-Et-DUPHOS-Rh

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C31H48F3O3P2RhS
CAS Number:
142184-30-3
Molecular Weight:
722.62
NACRES:
NA.22
PubChem Substance ID:
329761251
UNSPSC Code:
12352005
MDL number:
MFCD00269861

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI

1S/C22H36P2.C8H12.CHF3O3S.Rh/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4;1-2-4-6-8-7-5-3-1;2-1(3,4)8(5,6)7;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;(H,5,6,7);/q;;;+1/p-1/b;2-1-,8-7-;;/t17-,18-,19-,20-;;;/m0.../s1

SMILES string

[Rh+].[O-]S(=O)(=O)C(F)(F)F.C1CC=CCCC=C1.CC[C@H]2CC[C@H](CC)P2c3ccccc3P4[C@@H](CC)CC[C@@H]4CC

InChI key

HZLILTNLWVOBFS-ZCTOJWETSA-M

form

powder

General description

1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate is an electron-rich C2 symmetric bis(phospholane) ligand for enantioselective catalytic reactions.

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Catalyst involved in:
  • Oxidation of the δ-position via ruthenium catalysis
  • Stereoselective hydrogenation reactions of dehydroamino acid esters and macrocyclic peptideomimetics
  • Synthesis of cyclopeptide alkaloid mucronine E, fluoro-containing amino acids, and labeled protease inhibitors
(S,S)-Et-DUPHOS-Rh may be used as an efficient catalyst in the synthesis of (S)-2-quinolylalanine via asymmetric hydrogenation.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBX2370V
MKBL4291V
MKBH2901V
MKBF0770V
MKBC9840

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

DuPhos and BPE Phospholane Ligands and Complexes
Aldrich Chemfiles, 8(2), 34-34 (2008)
Preparation of (S)-2-quinolylalanine by asymmetric hydrogenation.
Jones SW, et al.
Tetrahedron Letters, 40(6), 1211-1214 (1999)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service