Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

668478

Sigma-Aldrich

(+)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]ethane

kanata purity

Synonym(s):

(R,R)-Et-BPE

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H36P2
CAS Number:
136705-62-9
Molecular Weight:
314.43
MDL number:
MFCD01073768
UNSPSC Code:
12352005
PubChem Substance ID:
24884985
NACRES:
NA.22

Quality Level

100

refractive index

n20/D 1.5249

bp

104-106 °C/0.05 mmHg

density

0.939 g/mL at 25 °C

functional group

phosphine

SMILES string

CC[C@@H]1CC[C@@H](CC)P1CCP2[C@H](CC)CC[C@H]2CC

InChI

1S/C18H36P2/c1-5-15-9-10-16(6-2)19(15)13-14-20-17(7-3)11-12-18(20)8-4/h15-18H,5-14H2,1-4H3/t15-,16-,17-,18-/m1/s1

InChI key

QOLRLVPABLMMKI-BRSBDYLESA-N

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
(+)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]ethane can be used as a reactant to prepare:
  • Chromium diphosphine chloride complex which is employed as a catalyst for chemoselective oligomerization reaction.
  • α-Arylpyrrolidines by Suzuki-Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions.

It can also be used as a catalyst in the enantioselective preparation of (perfluoroalkyl)butenyldiketones via cross Rauhut-Currier reaction of β-perfluoroalkylenones and vinyl ketones.

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
12721CE

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
Dai X-J, et al.
Angewandte Chemie (International Edition in English), 131(11), 3445-3449 (2019)

Articles

DuPhos and BPE Ligands

Asymmetric hydrogenation reactions represent the ideal process for the commercial manufacture of single-enantiomer compounds, because of the ease by which these robust procedures can be scaled up and because of the low levels of byproducts generated in these asymmetric hydrogenations.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service