(11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide
(11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide (CAS: 864943-22-6) is a complex chiral phosphoric acid derivative with the molecular formula C48H29O4P and a molecular weight of 700.72. This compound serves as a valuable chiral catalyst, particularly in asymmetric synthesis. Its unique structure facilitates high enantioselectivity in various organic transformations, making it a key reagent for advanced chemical synthesis.
- IUPAC
- (R)-3,3′-Bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate
- Synonyms
- 2′-f][1,3,2]dioxaphosphepin-4-oxide,864943-22-6, C48H29O4P
![(11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide — chemical structure, CAS 864943-22-6; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F864943-22-6.png&w=3840&q=75)
Asymmetric Hydrogenation
This catalyst is employed in asymmetric hydrogenation cascades, enabling the enantioselective synthesis of complex molecules. It is also effective in the asymmetric transfer hydrogenation of substituted quinoxalines.
Enantioselective Friedel-Crafts Reactions
It catalyses enantioselective Friedel-Crafts reactions, a crucial step in constructing chiral aromatic compounds. The catalyst's ability to control stereochemistry is vital for pharmaceutical intermediate synthesis.
Chiral Acid Catalysis
Utilised as a chiral Brønsted acid catalyst for enantioselective alpha-aminoxylation of ene carbamates. This application highlights its utility in generating stereodefined nitrogen-containing heterocycles.
Cyclization Cascade Reactions
The compound facilitates diastereo- and enantioselective N-acyliminium cyclization cascades of tryptamines and keto acids/esters, leading to the efficient preparation of chiral beta-carbolines.
Asymmetric Hydrogenation of Quinolines
It is specifically applied in the asymmetric hydrogenation of 2-substituted quinolines, offering a stereoselective route to chiral quinoline derivatives.
| Molecular weight | 700.72 |
|---|---|
| Empirical formula | C48H29O4P |
| Optical activity | [α]22/D −44.0°, c = 1 in DMSO |
| Storage temperature | −20°C |
| Application | Catalyst for:• Asymmetric hydrogenation cascade1• Enantioselective Friedel-Crafts reaction2• Asymmetric hydrogenation of 2-substituted quinolines3• Chiral Broensted acid catalyzed enantioselective a-aminoxylation of ene carbamates4• Preparation of β-carbolines via diastereo- and enantioselective N-acyliminium cyclization cascades of tryptamines and keto acids/esters5• Asymmetric transfer hydrogenation of substituted quinoxalines6 |
| Melting point | 390-400 °C |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide used for?
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This compound is primarily used as a chiral catalyst in asymmetric synthesis, including asymmetric hydrogenation, enantioselective Friedel-Crafts reactions, and cyclization cascades for preparing chiral molecules.
What is the CAS number and formula for this product?
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The CAS number is 864943-22-6, and the empirical formula (Hill notation) is C48H29O4P.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product for research and chemical synthesis purposes. The specific grade and purity are available upon request, and TSS does not represent this product as meeting USP, BP, EP, or other pharmacopoeial standards.
How should this chemical be handled and stored?
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Handle with appropriate personal protective equipment, including eyeshields, gloves, and a type N95 (US) or P1 (EN143) respirator filter. Store at -20°C. Refer to the safety data sheet for comprehensive handling information.
Is this chemical suitable for international export?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals, pharmaceutical intermediates, and laboratory reagents, and can arrange for the export of this product worldwide.
How can I request a sample or obtain a quote?
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To request a sample or obtain a quote, please contact our sales team through the website or by phone, providing the product name and CAS number.
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