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Merck
CN

700746

(S)-SDP

Synonym(s):

(S)-(−)-7,7′-Bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-1,1′-spirobiindene, (S)-7,7′-Bis(diphenylphosphino)-1,1′-spirobiindane

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About This Item

Empirical Formula (Hill Notation):
C41H34P2
CAS Number:
528521-86-0
Molecular Weight:
588.66
NACRES:
NA.22
PubChem Substance ID:
329762227
UNSPSC Code:
12352002
MDL number:
MFCD08459344

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InChI

1S/C41H34P2/c1-5-17-33(18-6-1)42(34-19-7-2-8-20-34)37-25-13-15-31-27-29-41(39(31)37)30-28-32-16-14-26-38(40(32)41)43(35-21-9-3-10-22-35)36-23-11-4-12-24-36/h1-26H,27-30H2

SMILES string

C1CC2(CCc3cccc(P(c4ccccc4)c5ccccc5)c23)c6c1cccc6P(c7ccccc7)c8ccccc8

InChI key

DKZNVWNOOLQCMJ-UHFFFAOYSA-N

form

solid

optical activity

[α]22/D −191°, c = 1 in chloroform

mp

199-204 °C

functional group

phosphine

storage temp.

−20°C

Quality Level

100

Related Categories

General description

(S)-SDP is a chiral diphosphine reagent used in the asymmetric hydrogenation of ketones catalyzed by transition metal. It is also used in hydrosilylation or cyclization of 1,6-enynes.

Application

(S)-SDP can be used:
  • As a ligand in the ruthenium-catalyzed asymmetric hydrogenation of cyclic ketones to give cycloalkanols.
  • To prepare ruthenium complexes, which are used in the asymmetric hydrogenation of different prochiral ketones.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5477
MKCQ1271
MKCP8572
MKCM1976
MKCH3977

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Dynamic Kinetic Resolution Allows a Highly Enantioselective Synthesis of cis-alpha-Aminocycloalkanols by Ruthenium-Catalyzed Asymmetric Hydrogenation
Liu S, et al.
Angewandte Chemie (International ed. in English), 46(39), 7506-7508 (2007)
Synthesis of spiro diphosphines and their application in asymmetric hydrogenation of ketones
Xie J, et al.
Journal of the American Chemical Society, 125(15), 4404-4405 (2003)
(R?and (S)?7,7′?Bis(diphenylphosphino)?2,2′,3,3′?tetrahydro?1,1′?spirobiindene
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2008)

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