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693618

Sigma-Aldrich

(2S,4S)-2,4-Bis(diphenylphosphino)pentane

97%

Synonym(s):

(S,S)-BDPP, [(1S,3S)-1,3-Dimethyl-1,3-propanediyl]bis[diphenylphosphine]

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About This Item

Empirical Formula (Hill Notation):
C29H30P2
CAS Number:
77876-39-2
Molecular Weight:
440.50
MDL number:
MFCD00058923
UNSPSC Code:
12352002
PubChem Substance ID:
329761604
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]20/D −125.0°, c = 1 in chloroform

mp

80-84 °C

functional group

phosphine

SMILES string

C[C@@H](C[C@H](C)P(c1ccccc1)c2ccccc2)P(c3ccccc3)c4ccccc4

InChI

1S/C29H30P2/c1-24(30(26-15-7-3-8-16-26)27-17-9-4-10-18-27)23-25(2)31(28-19-11-5-12-20-28)29-21-13-6-14-22-29/h3-22,24-25H,23H2,1-2H3/t24-,25-/m0/s1

InChI key

CTYPJIUQROQJBG-DQEYMECFSA-N

Application

Ligand used for asymmetric hydrogenation of ketones and alkenes

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

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
MKCN6138
MKCN2887
MKCK9956
MKCD9245
MKBW2524V

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Hideo Shimizu et al.
Organic letters, 9(9), 1655-1657 (2007-03-29)
[reaction: see text] A novel asymmetric hydrogenation protocol using a copper catalyst is reported. A Cu(I) complex in the presence of nonracemic BDPP hydrogenates aryl ketones with moderate to high enantioselectivity.
Shui-Ming Lu et al.
Journal of the American Chemical Society, 130(20), 6451-6455 (2008-05-01)
The intramolecular cyclocarbonylation reaction with palladium-complexed dendrimers on silica is a very effective method for the regioselective synthesis of methylene 8-, 9-, and 10-membered rings. The heterogeneous dendritic catalysts are easily recovered by simple filtration and reused for up to

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