(S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’]dinaphthalen-4-yl)bis(1-phenylethyl)amine
(S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’]dinaphthalen-4-yl)bis(1-phenylethyl)amine (CAS 380230-02-4), with the molecular formula C36H30NO2P and a molecular weight of 539.60 g/mol, is a chiral phosphoramidite ligand. This compound is recognised for its utility in asymmetric synthesis, particularly in enantioselective catalytic reactions. It serves as a crucial component in facilitating complex molecular transformations with high stereochemical control in chemical synthesis.
- IUPAC
- (+)-N,N-Bis[(1S)-1-phenylethyl]- dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin- 4-amine, (11bR)
- Synonyms
- (S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’)dinaphthalen-4-yl)bis(1-phenylethyl)amine(+)-N,N-Bis[(1S)-1-phenylethyl]-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, (11bR)
![(S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’]dinaphthalen-4-yl)bis(1-phenylethyl)amine (S)-(+)-(3) — chemical structure, CAS 380230-02-4; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F380230-02-4.png&w=3840&q=75)
Enantioselective Conjugate Addition
This phosphoramidite ligand is employed in copper-catalyzed conjugate addition reactions of dialkylzincs to various Michael acceptors, achieving high enantioselectivity in the formation of chiral products.
Umpolung Allylation Reactions
It finds application in palladium-catalyzed diethylzinc-mediated umpolung allylation, a process enabling the formation of carbon-carbon bonds with controlled stereochemistry.
Asymmetric Synthesis
As a privileged chiral ligand, it is integral to various asymmetric synthesis strategies, facilitating the creation of enantiomerically enriched molecules crucial for pharmaceutical and fine chemical development.
| Molecular weight | 539.60 |
|---|---|
| Empirical formula | C36H30NO2P |
| Assay | 97% |
| Application | Chiral phosphoramidite ligand used in a highly enantioselective copper-catalyzed conjugate addition of diakylzincs to a variety of Michael acceptors.1,2,3 Also used in a palladium-catalyzed diethylzinc mediated umpolung allylation.4 |
| Melting point | 88-89 °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 (S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’]dinaphthalen-4-yl)bis(1-phenylethyl)amine used for?
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This compound is used as a chiral phosphoramidite ligand in asymmetric synthesis, notably in enantioselective copper-catalyzed conjugate addition reactions and palladium-catalyzed umpolung allylation.
What is the CAS number and formula for this phosphoramidite?
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The CAS number is 380230-02-4, and the empirical formula is C36H30NO2P.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with an assay of 97%. We do not represent this product as USP, BP, EP, or pharmacopoeia grade.
What safety precautions should be taken when handling this chemical?
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Handling requires appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter should be used. This compound has a WGK Germany rating of 3, indicating it is hazardous.
Is this chemical packed, shipped, or exported by TSS?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including this compound.
How can I request a quote or sample?
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Please contact our sales team through the website to request a quote or a sample of this product.
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