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682144

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

96%

Synonym(s):

(R)-Phanephos

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100 mg
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$138.00
500 mg
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$627.00

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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Quality Segment

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

Application

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

Legal Information

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

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67580667551216702
(R)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane 96%

Sigma-Aldrich

682144

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

(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine 97%

Sigma-Aldrich

675806

(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine

(R)-(–)-VAPOL hydrogenphosphate

Sigma-Aldrich

675512

(R)-(–)-VAPOL hydrogenphosphate

(R)-Pantetheine ≥95.0% (HPLC)

Sigma-Aldrich

16702

(R)-Pantetheine

description

96%

description

97%

description

-

description

≥95.0% (HPLC)

assay

96%

assay

97%

assay

-

assay

≥95.0% (HPLC)

functional group

phosphine

functional group

phosphine

functional group

-

functional group

-

form

solid

form

solid

form

solid

form

solid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

mp

222-226 °C

mp

261-265 °C

mp

-

mp

-

optical activity

[α]/D -34±4°, c = 1 in chloroform

optical activity

[α]20/D +98°, c = 1 in chloroform

optical activity

-

optical activity

[α]/D 17±2°, c = 1 in H2O

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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