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682985

Sigma-Aldrich

(11bS, 11′bS)-4,4′-(Oxydi-2,1-phenylene)bis-dinaphtho[2,1-d: 1′, 2′-f][1,3,2]dioxaphosphepin

Synonym(s):

S, S-Reetz D-Diphosphonite

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About This Item

Empirical Formula (Hill Notation):
C52H32O5P
CAS Number:
898830-89-2
Molecular Weight:
767.78
MDL number:
MFCD09842741
UNSPSC Code:
12352005
PubChem Substance ID:
329760785
NACRES:
NA.22

form

solid

optical activity

[α]22/D -85.0°, c = 1 in chloroform

mp

174-186 °C

SMILES string

O1P(Oc2ccc3ccccc3c2-c4c1ccc5ccccc45)c6ccccc6Oc7ccccc7P8Oc9ccc%10ccccc%10c9-c%11c(O8)ccc%12ccccc%11%12

InChI

1S/C52H32O5P2/c1-5-17-37-33(13-1)25-29-43-49(37)50-38-18-6-2-14-34(38)26-30-44(50)55-58(54-43)47-23-11-9-21-41(47)53-42-22-10-12-24-48(42)59-56-45-31-27-35-15-3-7-19-39(35)51(45)52-40-20-8-4-16-36(40)28-32-46(52)57-59/h1-32H

InChI key

UYGCVTAJLJBNHG-UHFFFAOYSA-N

Application

This diphosphonite ligand has been successfully employed in asymmetric Rh-catalyzed conjugate addition reactions of arylboronic acids to enones, as well as in asymmetric hydrogenation reactions of β-keto esters.

signalword

Danger

Hazard Classifications

Flam. Sol. 1 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 Inhalation - STOT SE 3

target_organs

Central nervous system

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
04515PH
03212HH

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Reetz, M. T.; Li, X.
Advanced Synthesis & Catalysis, 348, 1157-1157 (2006)
M T Reetz et al.
Organic letters, 3(25), 4083-4085 (2001-12-12)
[reaction: see text] BINOL-based diphosphonites having achiral backbones are useful ligands in the Rh-catalyzed conjugate addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds. The nature of the achiral backbone determines the direction and degree of enantioselectivity, with er values of

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