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Merck
CN

668486

(+)-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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24884986
MDL number:
MFCD00142321
Beilstein/REAXYS Number:
4814174

Key Documents

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SMILES string

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

InChI key

GVVCHDNSTMEUCS-MUGJNUQGSA-N

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

refractive index

n20/D 1.581

density

1.010 g/mL at 25 °C

functional group

phosphine

Quality Level

100

Related Categories

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM2398
MKCM2695
MKCF7421
MKCG5105
MKBQ2944V

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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)
Asymmetric synthesis of γ-butyrolactones by enantioselective hydrogenation of butenolides
Donate PM, et al.
Tetrahedron Asymmetry, 14(20), 3253-3256 (2003)
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)
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)

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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