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668478

Sigma-Aldrich

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

kanata purity

Synonym(s):

(R,R)-Et-BPE

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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

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

Related Categories

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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.

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