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Merck
CN

668494

(−)-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:
136705-64-1
Molecular Weight:
362.47
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24884987
MDL number:
MFCD00142335
Beilstein/REAXYS Number:
4814174

Key Documents

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InChI key

GVVCHDNSTMEUCS-UAFMIMERSA-N

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

SMILES string

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

refractive index

n20/D 1.6

density

1.01 g/mL at 25 °C

functional group

phosphine

Quality Level

100

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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.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBQ9360V
12621CE

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Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity
Berger A, et al.
Tetrahedron Asymmetry, 12(13), 1825-1828 (2001)
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)

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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