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Merck
CN

682144

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

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

Key Documents

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Product Name

(R)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane, 96%

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

assay

96%

form

solid

optical activity

[α]/D -34±4°, c = 1 in chloroform

mp

222-226 °C

functional group

phosphine

Quality Level

100

Related Categories

Legal Information

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

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.

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
MKCV7286
MKCQ0829
MKCL4560
MKCF8307
MKCC8744

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Enantioselective synthesis of the bromopyrrole alkaloids manzacidin A and C by stereospecific C? H bond oxidation
Wehn, Paul M., and J. Du Bois
Journal of the American Chemical Society, 124.44, 12950-12951 (2002)
Highly efficient thermally activated fluorescence of a new rigid Cu (I) complex [Cu (dmp)(phanephos)]+
Czerwieniec, Rafal, Konrad Kowalski, and Hartmut Yersin
Dalton Transactions, 42.27, 9826-9830 (2013)
Synthesis, structural analysis, and chiral investigations of some atropisomers with ee-tetrahalogeno-1, 3-butadiene core
Piron, Flavia, et al.
The Journal of Organic Chemistry, 74.23, 9062-9070 (2009)
Diversity of copper (I) complexes showing thermally activated delayed fluorescence: basic photophysical analysis
Czerwieniec, Rafal, and Hartmut Yersin
Inorganic Chemistry, 54.9, 4322-4327 (2015)
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)
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