Skip to Content
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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

ppe

Eyeshields, Gloves, type N95 (US)

flash_point_f

No data available

flash_point_c

No data available

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCX5477
MKCQ1271
MKCP8572
MKCM1976
MKCH3977

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

(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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service