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

Name: (<I>R</I>)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane
Brand: ALDRICH
Price: 99 USD
Availability: InStock

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

MDL number:

MFCD03094575

UNSPSC Code:

12352002

PubChem Substance ID:

24885681

NACRES:

NA.22

Key Documents

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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

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Catalysts

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1 of 4

This Item	682136	259128	675806
Sigma-Aldrich 682144 (R)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane	Sigma-Aldrich 682136 (S)-(+)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane	Sigma-Aldrich 259128 (R)-(+)-1,2-Bis(diphenylphosphino)propane	Sigma-Aldrich 675806 (R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine
assay 96%	assay 96%	assay 98%	assay 97%
form solid	form solid	form solid	form solid
functional group phosphine	functional group phosphine	functional group phosphine	functional group phosphine
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
mp 222-226 °C	mp 224-226 °C	mp 71-73 °C (lit.)	mp 261-265 °C
optical activity [α]/D -34±4°, c = 1 in chloroform	optical activity [α]22/D +34°, c = 1 in chloroform	optical activity [α]20/D +184°, c = 1 in acetone	optical activity [α]20/D +98°, c = 1 in chloroform

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.[1]
Asymmetric hydroboration of 3,3-disubstituted cyclopropenes to form 2,2-disubstituted cyclopropyl boronates.[2]
Asymmetric ring-opening reactions of azabenzonorbornadienes in the presence of zinc(II) triflate and palladium(II) acetate to form aminodihydronaphthalenes.[3]

Efficient ligand for asymmetric hydrogentation of dehydroamino acids, methyl esters and keytones.[4][5]

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

Highly efficient ruthenium-catalyzed oxime to amide rearrangement

Owston, Nathan A., Alexandra J. Parker, and Jonathan MJ Williams

Organic Letters, 9.18, 3599-3601 (2007)

[2.2] Paracyclophane Derivatives: Synthesis and Application in Catalysis

Paradies, Jan

Synthesis, 2011.23, 3749-3766 (2011)

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