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668524

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

Name: (+)-1,2-Bis[(2<I>R</I>,5<I>R</I>)-2,5-diisopropylphospholano]benzene
Brand: ALDRICH

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.
Rhodium catalyzed enantioselective synthesis of 1,2 diols via asymmetric intramolecular hydrosilylation of α- and β-hydroxyketones.
In the enantioselective synthesis of diarylmethanols by arylation of aromatic aldehydes with arylboronic acids in the presence of a rhodium catalyst.

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.

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

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 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)

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)

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)

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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