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668486

Sigma-Aldrich

(+)-1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene

Namena purity

Synonym(s):

(2S,2′S,5S,5′S)-2,2′,5,5′-Tetraethyl-1,1′-(o-phenylene)diphospholane, (S,S)-Ethyl-DUPHOS

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About This Item

Empirical Formula (Hill Notation):
C22H36P2
CAS Number:
136779-28-7
Molecular Weight:
362.47
Beilstein:
4814174
MDL number:
MFCD00142321
UNSPSC Code:
12352005
PubChem Substance ID:
24884986
NACRES:
NA.22

refractive index

n20/D 1.581

density

1.010 g/mL at 25 °C

SMILES string

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

InChI

1S/C22H36P2/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4/h9-12,17-20H,5-8,13-16H2,1-4H3/t17-,18-,19-,20-/m0/s1

InChI key

GVVCHDNSTMEUCS-MUGJNUQGSA-N

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Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
(+)-1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene is a chiral ligand that can be used to prepare its rhodium metal complexes, which are used as catalysts in asymmetric hydrogenation reactions.

Legal Information

Sold in collaboration with Namena Corp. 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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Asymmetric synthesis of γ-butyrolactones by enantioselective hydrogenation of butenolides
Donate PM, et al.
Tetrahedron Asymmetry, 14(20), 3253-3256 (2003)
An efficient chiral synthesis of fluoro-containing amino acids: N-benzyloxycarbonyl-2-amino-4, 4-difluorobutyric acid methyl ester and its analogs
Hu Z and Han W
Tetrahedron Letters, 49(5), 901-902 (2008)
Assymetric synthesis of (2S, 3R)-and (2S, 3S)-[2-13C; 3-2H] glutamic acid
Okuma K, et al.
Tetrahedron Letters, 50(13), 1482-1484 (2009)
Synthesis of stereoarray isotope labeled (SAIL) lysine via the ?Head-to-Tail? conversion of SAIL glutamic Acid
Terauchi T, et al.
Organic Letters, 13(1), 161-163 (2011)

Articles

DuPhos and BPE Ligands

Asymmetric hydrogenation enables scalable synthesis of single-enantiomer compounds with minimal byproducts, ideal for commercial manufacturing.

DuPhos and BPE Ligands

Asymmetric hydrogenation enables scalable synthesis of single-enantiomer compounds with minimal byproducts, ideal for commercial manufacturing.

DuPhos and BPE Ligands

Asymmetric hydrogenation enables scalable synthesis of single-enantiomer compounds with minimal byproducts, ideal for commercial manufacturing.

DuPhos and BPE Ligands

Asymmetric hydrogenation enables scalable synthesis of single-enantiomer compounds with minimal byproducts, ideal for commercial manufacturing.

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