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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[1] and alkenes[2]

Hazard Statements

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

693618-VAR:
693618-1G:
693618-500MG:
693618-BULK:

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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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