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668524

Sigma-Aldrich

(+)-1,2-Bis[(2R,5R)-2,5-diisopropylphospholano]benzene

kanata purity

Synonym(s):

(R,R)-i-Pr-DUPHOS

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About This Item

Empirical Formula (Hill Notation):
C26H44P2
CAS Number:
136705-65-2
Molecular Weight:
418.58
MDL number:
MFCD02684549
UNSPSC Code:
12352005
PubChem Substance ID:
24884989
NACRES:
NA.22

form

solid

optical activity

[α]20/D +103°, c = 1 in chloroform

refractive index

n20/D 1.5701

SMILES string

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

InChI

1S/C26H44P2/c1-17(2)21-13-14-22(18(3)4)27(21)25-11-9-10-12-26(25)28-23(19(5)6)15-16-24(28)20(7)8/h9-12,17-24H,13-16H2,1-8H3/t21-,22-,23-,24-/m1/s1

InChI key

RBVGOQHQBUPSGX-MOUTVQLLSA-N

General description

Optical rotation devation ± 13

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
(R,R)-i-Pr-DUPHOS is a chiral phospholane class of ligand that can be used in:
  • The catalytic asymmetric hydrogenation reactions.[1][2]
  • Rhodium catalyzed enantioselective synthesis of 1,2 diols via asymmetric intramolecular hydrosilylation of α- and β-hydroxyketones.[3]
  • In the enantioselective synthesis of diarylmethanols by arylation of aromatic aldehydes with arylboronic acids in the presence of a rhodium catalyst.[4]

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.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS0345V
30196LJV
30196LJ
04318HJ
09016EE

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Enantioselective hydrogenation of imines using a diverse library of ruthenium dichloride (diphosphine)(diamine) precatalysts
Cobley CJ and Henschke JP
advanced synthesis and catalysis, 345(1-2), 195-201 (2003)
Asymmetric hydrogenation of a 4, 4-diaryl-3-butenoate; a novel approach to sertraline
Boulton LT, et al.
Organic & Biomolecular Chemistry, 1(7), 1094-1096 (2003)
Asymmetric synthesis of diarylmethanols by Rh (I)-catalyzed arylation of aromatic aldehydes with arylboronic acid
Suzuki K, et al.
Synthesis, 2006(08), 1360-1364 (2006)
Asymmetric intramolecular hydrosilylation of hydroxyketones
Burk MJ and Feaster JE
Tetrahedron Letters, 33(16), 2099-2102 (1992)
Enantioselective hydrogenation of imines using a diverse library of ruthenium dichloride (diphosphine)(diamine) precatalysts
Cobley CJ and Henschke JP
Advanced Synthesis & Catalysis, 345(1-2), 195-201 (2003)

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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