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ChemicalBook >  Product Catalog >  Organic Chemistry >  (+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE

(+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE

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(+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE Basic information

Product Name:
(+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE
Synonyms:
  • (+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE
  • (R,R)-ET-BPE
  • Bisdiethylphospholanoethane
  • (+)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]ethane, Kanata purity
  • (+)-1,2-Bis[(2R,5R)-2,5-diethyl-1-phospholanyl]ethane, 97+%
  • (+)-1,2-Bis((2R,5R)-2,5-diethylphospholano)ethane,98+%(R,R)-Et-BPE
  • (+)-1,2-Bis((2R,5R)-2,5-diethylphospholano)ethane (R,R)-Et-BPE
  • (2R,5R)-1-[2-[(2R,5R)-2,5-diethylphospholan-1-yl]ethyl]-2,5-diethylphospholane
CAS:
136705-62-9
MF:
C18H36P2
MW:
314.43
Product Categories:
  • organophosphine ligand
Mol File:
136705-62-9.mol
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(+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE Chemical Properties

Boiling point:
104-106°C 0,5mm
alpha 
+320° ±4° (c 1, hexane)
Density 
0.939 g/mL at 25 °C
refractive index 
n20/D 1.5249
Flash point:
110 °C
form 
liquid
color 
colorless to pale-yellow
Sensitive 
Air Sensitive
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
InChIKey
QOLRLVPABLMMKI-BRSBDYLESA-N
SMILES
CC[C@@H]1CC[C@@H](CC)P1CCP2[C@H](CC)CC[C@H]2CC
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
WGK Germany 
3
HazardClass 
4.2
Storage Class
10 - Combustible liquids
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(+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANE Usage And Synthesis

Reaction

  1. The DUPHOS family of catalysts is highly efficient for the asymmetric hydrogenation of various substituted acetamidoacrylates and enol acetates yielding products of high enantiomeric excesses. Efficient ligand for the asymmetric hydrogenation of tetrasubstituted enamides.
  2. Forms superior catalysts for asymmetric reductive aminations.
  3. Catalyst used for the asymmetric hydrogenation of enol phosphonates.
  4. A novel enantioselective synthesis of β-amino alcohols and 1,2-diamines.
  5. Ligand for the catalytic asymmetric [4+1] cycloaddition of vinylallenes with CO.
  6. Ligand for the Rh-catalyzed asymmetric enyne cycloisomerization.
  7. Catalytic enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines.
  8. Palladium catalyzed asymmetric phosphination. 


Uses

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.

(+)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)ETHANESupplier

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