682144

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

96%

• Synonym(s): (R)-Phanephos
• 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

Properties

• 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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves