(R)-VANOL
(R)-VANOL, CAS 147702-13-4, with the molecular formula C32H22O2 and a molecular weight of 438.52, is a BINOL-derived chiral ligand. It is highly valued in asymmetric synthesis for its efficacy in promoting stereoselective transformations. This compound serves as a critical chiral auxiliary and catalyst component in various organic reactions, enabling the efficient synthesis of enantiomerically enriched products.
- IUPAC
- (R)-3,3′-Diphenyl-2,2′-bi-1-naphthalol,(R)-3,3′-Diphenyl-2,2′-bi-1-naphthol
- Synonyms
- (R)-3,3′-Diphenyl-2,2′-bi-1-naphthalol(R)-3,3′-Diphenyl-2,2′-bi-1-naphthol
Asymmetric Catalysis
VANOL is a well-established chiral ligand used in metal-catalyzed asymmetric reactions. Its structure facilitates high enantioselectivity in transformations such as Diels-Alder cycloadditions and aldol reactions, crucial for producing chiral molecules.
Diels-Alder Reactions
As a ligand, VANOL has demonstrated effectiveness in catalyzing asymmetric Diels-Alder reactions. This application is vital for the stereocontrolled formation of cyclic compounds, frequently employed in the synthesis of complex natural products and pharmaceuticals.
Imine Aldol Reactions
VANOL serves as an excellent ligand for catalytic asymmetric imine aldol reactions. These reactions are important for constructing chiral amines and related nitrogen-containing compounds with high stereochemical control.
Aziridination Reactions
The compound is also recognised for its utility in asymmetric aziridination reactions. This allows for the stereoselective synthesis of chiral aziridines, valuable intermediates in medicinal chemistry and organic synthesis.
| Molecular weight | 438.52 |
|---|---|
| Empirical formula | C32H22O2 |
| Assay | 97% |
| Optical activity | [α]20/D +310°, c = 1 in chloroform |
| Application | VANOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.1,2,3 |
| Melting point | 200-204 °C |
Hazard statements
- H315Causes skin irritation
- H318Causes serious eye damage
- H335May cause respiratory irritation
- H413May cause long-lasting harmful effects to aquatic life
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 37/38-41 |
| Safety statements (S) | 26-39 |
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 (R)-VANOL primarily used for?
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Primarily, (R)-VANOL is used as a chiral ligand in asymmetric synthesis, notably in Diels-Alder, imine aldol, and aziridination reactions, to achieve high enantioselectivity.
What are the CAS number and chemical formula for (R)-VANOL?
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(R)-VANOL has the CAS number 147702-13-4 and the molecular formula C32H22O2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (R)-VANOL with an assay of 97%. This product is not designated as USP, BP, or EP grade.
How should (R)-VANOL be handled safely?
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Handle (R)-VANOL with appropriate personal protective equipment, including a dust mask (N95), eyeshields, and gloves. It is classified as a danger substance, causing skin irritation, serious eye damage, and respiratory irritation (H315, H318, H335).
Is (R)-VANOL available for export by TSS?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals, including (R)-VANOL.
How can I request a sample or quote for (R)-VANOL?
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Please contact the TSS sales team directly through our website or by phone to request a sample or a quotation for (R)-VANOL.
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