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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

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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

Quality Level

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

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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

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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)
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

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.

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