Skip to Content
Merck
All Photos(1)

Key Documents

668494

Sigma-Aldrich

(−)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene

kanata purity

Synonym(s):

(2R,2′R,5R,5′R)-2,2′-5,5′-Tetraethyl-1,1′-(o-phenylene)diphospholane, (R,R)-Ethyl-DUPHOS

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C22H36P2
CAS Number:
Molecular Weight:
362.47
Beilstein:
4814174
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

refractive index

n20/D 1.6

density

1.01 g/mL at 25 °C

functional group

phosphine

SMILES string

CC[C@@H]1CC[C@@H](CC)P1c2ccccc2P3[C@H](CC)CC[C@H]3CC

InChI

1S/C22H36P2/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/h9-12,17-20H,5-8,13-16H2,1-4H3/t17-,18-,19-,20-/m1/s1

InChI key

GVVCHDNSTMEUCS-UAFMIMERSA-N

Looking for similar products? Visit Product Comparison Guide

Application

(−)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene is a chiral ligand that can be used to prepare the Duphos-Rhodium metal complex, which is used as a catalyst in asymmetric hydrogenation reactions.

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.

Hazard Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

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.

Already Own This Product?

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

Visit the Document Library

An enantioselective synthesis of beta2-amino acid derivatives
Elaridi J, et al.
Tetrahedron Asymmetry, 16(7), 1309-1319 (2005)
Enantioselective hydrogenation in ionic liquids: Recyclability of the [Rh (COD)(DIPAMP)] BF4 catalyst in [bmim][BF4]
Frater T, et al.
Inorgorganica Chimica Acta, 359(9), 2756-2759 (2006)
Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity
Berger A, et al.
Tetrahedron Asymmetry, 12(13), 1825-1828 (2001)
1,2?Bis(2,5?diethylphospholano)benzene
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

Articles

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

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

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

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

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