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668494

Sigma-Aldrich

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

kanata purity

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Synonym(s):
(2R,2′R,5R,5′R)-2,2′-5,5′-Tetraethyl-1,1′-(o-phenylene)diphospholane, (R,R)-Ethyl-DUPHOS
Empirical Formula (Hill Notation):
C22H36P2
CAS Number:
136705-64-1
Molecular Weight:
362.47
Beilstein:
4814174
MDL number:
MFCD00142335
UNSPSC Code:
12352005
PubChem Substance ID:
24884987
NACRES:
NA.22

Quality Level

100

refractive index

n20/D 1.6

density

1.01 g/mL at 25 °C

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

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Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
(−)-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

H413

Hazard Classifications

Aquatic Chronic 4

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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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)
An enantioselective synthesis of beta2-amino acid derivatives
Elaridi J, et al.
Tetrahedron Asymmetry, 16(7), 1309-1319 (2005)
1,2?Bis(2,5?diethylphospholano)benzene
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity
Berger A, et al.
Tetrahedron Asymmetry, 12(13), 1825-1828 (2001)

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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