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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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50 MG

$272.00

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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

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This Item
70075470085176854
(S)-SDP

Sigma-Aldrich

700746

(S)-SDP

(R)-SDP

Sigma-Aldrich

700754

(R)-SDP

(S)-Xyl-SDP

Sigma-Aldrich

700851

(S)-Xyl-SDP

(S)-(−)-5,5′-Dichloro-2,2′-bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl ≥97.0% (H-NMR)

Sigma-Aldrich

76854

(S)-(−)-5,5′-Dichloro-2,2′-bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl

assay

≥95%

assay

-

assay

-

assay

≥97.0% (H-NMR)

form

solid

form

solid

form

solid

form

crystals

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

chloro, phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

optical activity

[α]22/D −191°, c = 1 in chloroform

optical activity

[α]22/D +184°, c = 1 in chloroform

optical activity

[α]22/D −62.0°, c = 1 in chloroform

optical activity

[α]20/D −59.0±4°, c = 1% in chloroform

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.[1]

Application

(S)-SDP can be used:
  • As a ligand in the ruthenium-catalyzed asymmetric hydrogenation of cyclic ketones to give cycloalkanols.[2]
  • To prepare ruthenium complexes, which are used in the asymmetric hydrogenation of different prochiral ketones.[3]

related product

Product No.
Description
Pricing

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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(R?and (S)?7,7′?Bis(diphenylphosphino)?2,2′,3,3′?tetrahydro?1,1′?spirobiindene
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2008)
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)

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