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682144

(R)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane

Name: (<I>R</I>)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane
Brand: ALDRICH

96%

Synonym(s):

(R)-Phanephos

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About This Item

Empirical Formula (Hill Notation):

C₄₀H₃₄P₂

CAS Number:

364732-88-7

Molecular Weight:

576.65

UNSPSC Code:

12352002

PubChem Substance ID:

24885681

NACRES:

NA.22

MDL number:

MFCD03094575

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Properties

Quality Level

100

assay

96%

form

solid

optical activity

[α]/D -34±4°, c = 1 in chloroform

mp

222-226 °C

functional group

phosphine

SMILES string

P(c7ccccc7)(c6ccccc6)c1c2ccc(c1)CCc3c(cc(cc3)CC2)P(c5ccccc5)c4ccccc4

InChI

1S/C40H34P2/c1-5-13-35(14-6-1)41(36-15-7-2-8-16-36)39-29-31-21-25-33(39)27-23-32-22-26-34(28-24-31)40(30-32)42(37-17-9-3-10-18-37)38-19-11-4-12-20-38/h1-22,25-26,29-30H,23-24,27-28H2

InChI key

GYZZZILPVUYAFJ-UHFFFAOYSA-N

Description

Application

(R)-(-)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane may be used as a ligand in the following processes:

Enantioselective reductive cyclization of 1,6-enynes via asymmetric hydrogenation in the presence of a rhodium catalyst to form alkylidene-substituted heterocycles.
Asymmetric hydroboration of 3,3-disubstituted cyclopropenes to form 2,2-disubstituted cyclopropyl boronates.
Asymmetric ring-opening reactions of azabenzonorbornadienes in the presence of zinc(II) triflate and palladium(II) acetate to form aminodihydronaphthalenes.

Efficient ligand for asymmetric hydrogentation of dehydroamino acids, methyl esters and keytones.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US5874629 and any patents arising therefrom apply.

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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Articles

P-Phos, PhanePhos and BoPhoz™ Ligands

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

Enantioselective Reductive Cyclization of 1, 6-Enynes via Rhodium-Catalyzed Asymmetric Hydrogenation: C- C Bond Formation Precedes Hydrogen Activation.

Jang HY, et al.

Journal of the American Chemical Society, 127(17), 6174-6175 (2005)

Amide bond formation via C (sp 3)?H bond functionalization and CO insertion

Liu, Huizhen, et al.

Chemical Communications (Cambridge, England), 50.3, 341-343 (2014)

Catalytic enantioselective hydroboration of cyclopropenes.

Rubina M, et al.

Journal of the American Chemical Society, 125(24), 7198-7199 (2003)

View All Related Papers

Global Trade Item Number

SKU	GTIN
682144-500MG	04061833540787
682144-100MG	04061833549964