(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (CAS 76189-56-5) is a chiral phosphine ligand with a molecular weight of 622.67. This BINAP derivative is crucial in asymmetric synthesis, acting as a key component in chiral catalysts. Its applications span enantioselective reactions, the synthesis of biologically active organophosphine oxides, and SN2 halogenations, making it an indispensable tool for advanced chemical research and development.
- IUPAC
- (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine),(S)-(−)-BINAP
- Synonyms
- 76189-56-5[(C6H5)2PC10H6-]2(S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)(S)-(−)-BINAP
![(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene ([(C6H5)2PC10H6-]2) — chemical structure, CAS 76189-56-5; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F76189-56-5.png&w=3840&q=75)
Enantioselective Carbonyl Allylation
This chiral ligand is employed in enantioselective and diastereoselective unpoled carbonyl allylation reactions, enabling the synthesis of stereochemically defined products.
Synthesis of Organophosphine Oxides
It serves as a reactant in the synthesis of organophosphine oxides, a class of compounds investigated for potential antitumor activity.
SN2 Halogenation Reactions
The compound facilitates SN2 halogenation of hydroxyl groups, a valuable transformation in organic synthesis for introducing halogen substituents.
BINAP Complex Synthesis
It is instrumental in the preparation of BINAP complexes, which are widely used as catalysts in various asymmetric transformations.
Conformational Studies
Used in studies to investigate the conformational flexibility of BINAP chelates, contributing to a deeper understanding of catalyst behaviour.
| Molecular weight | 622.67 |
|---|---|
| Linear formula | [(C6H5)2PC10H6-]2 |
| Optical activity | [α]20/D −239±5°, c = 0.3% in toluene |
| Optical purity | enantiomeric ratio: ≥99.5:0.5 (HPLC) |
| Application | Reactant involved in:• Enantioselective and diastereoselective unpoled carbonyl allylation1• Syntehsis of organophophine oxides as anittumor agents2• SN2 halogenation of hydroxy groups3• Synthesis of BINAP complexes4,5• Studies of conformational flexibility of BINAP chelates6 |
| Melting point | 238-240 °C(lit.)238-242 °C (dec.) |
| 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)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene used for?
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(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is primarily used as a chiral ligand in asymmetric synthesis, for enantioselective carbonyl allylation, synthesis of organophosphine oxides with potential antitumor activity, and SN2 halogenation of hydroxyl groups.
What is the CAS number and formula for this compound?
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The CAS number is 76189-56-5. The linear formula is [(C₆H₅)₂PC₁₀H₆-]₂.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene with an enantiomeric ratio of ≥99.5:0.5 (HPLC). TSS does not represent this product as USP/BP/EP or any other pharmacopoeia grade.
How should (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene be handled?
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Handling requires appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter is recommended. This compound is classified under WGK 3 in Germany.
Is this product available for international export?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene.
How can I request a quote or sample?
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Please contact our customer service team via the website or email to request a quote or sample of (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene.
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