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(S)-(−)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine

Name: (<I>S</I>)-(−)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine
Brand: ALDRICH

97%

Synonym(s):

(S)-P-Phos

About This Item

Empirical Formula (Hill Notation):

C₃₈H₃₄N₂O₄P₂

CAS Number:

362524-23-0

Molecular Weight:

644.64

NACRES:

NA.22

PubChem Substance ID:

24885300

UNSPSC Code:

12352005

MDL number:

MFCD04038734

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Properties

assay

97%

optical activity

[α]20/D -98°, c = 1 in chloroform

mp

261-265 °C

functional group

phosphine

SMILES string

COc1cc(P(c2ccccc2)c3ccccc3)c(c(OC)n1)-c4c(OC)nc(OC)cc4P(c5ccccc5)c6ccccc6

InChI

1S/C38H34N2O4P2/c1-41-33-25-31(45(27-17-9-5-10-18-27)28-19-11-6-12-20-28)35(37(39-33)43-3)36-32(26-34(42-2)40-38(36)44-4)46(29-21-13-7-14-22-29)30-23-15-8-16-24-30/h5-26H,1-4H3

InChI key

JZOSBBLJKXSBBN-UHFFFAOYSA-N

Description

Application

Ligand employed in the asymmetic hydrogenation of β-keto esters, 2-arylacrylates, aryl ketones , and other substrates.[1]

(S)-P-Phos can be used as a ligand:

In the asymmetic hydrogenation reactions.
For the preparation of chiral ketone functionalized polymers by copolymerization reaction.
To synthesize chiral alkynes by asymmetric hydroalkynylation of nonpolar alkenes or norbornadienes using iridium catalyst.
In the selective allylic alkylation of indoles using palladium catalyst.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US5886182 and any patents arising therefrom apply.

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1 of 1

This Item	675806	676004	295825
Sigma-Aldrich 675792 (S)-(−)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine	Sigma-Aldrich 675806 (R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine	Sigma-Aldrich 676004 (R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(di(3,5-xylyl)phosphino)-3,3′-bipyridine	Sigma-Aldrich 295825 (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
assay 97%	assay 97%	assay 97%	assay 97%
functional group phosphine	functional group phosphine	functional group phosphine	functional group phosphine
mp 261-265 °C	mp 261-265 °C	mp 190-194 °C	mp 238-240 °C (lit.)
optical activity [α]20/D -98°, c = 1 in chloroform	optical activity [α]20/D +98°, c = 1 in chloroform	optical activity [α]20/D +125°, c = 1 in chloroform	optical activity [α]19/D −233°, c = 0.3 in toluene

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

MKBF7298V

04216HE

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Articles

P-Phos, PhanePhos and BoPhoz™ Ligands

P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

Asymmetric hydrogenation of isobutyrophenone using a [(diphosphine) rucl2 (1, 4-diamine)] catalyst

Grasa, Gabriela A and Zanotti-Gerosa, Antonio and Medlock, Jonathan A and Hems, William P

Organic Letters, 7(8), 1449-1451 (2005)

Asymmetric hydroalkynylation of norbornadienes promoted by chiral iridium catalysts

Fan B-M, et al.

Angewandte Chemie (International Edition in English), 51(31), 7821-7824 (2012)

Enantioselective Pd-catalyzed allylic alkylation of indoles by a new class of chiral ferrocenyl P/S ligands

Cheung HY, et al.

Organic Letters, 9(21), 4295-4298 (2007)

View All Related Papers

Global Trade Item Number

SKU	GTIN
675792-500MG	04061833549667
675792-100MG	04061833549650

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