| Size | Price | Stock | Qty |
|---|---|---|---|
| 25g |
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| 50g |
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| Other Sizes |
| Targets |
(R)-BINAP does not have a defined pharmacological target. It is a chiral chelating ligand used in asymmetric catalysis. Its mechanism of action is chemical: the ligand coordinates to metal centers to form chiral catalysts that promote enantioselective reactions. It is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses.
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|---|---|
| ln Vitro |
In metal-mediated asymmetric catalysis, (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthy is employed as a chiral ligand.
In vitro, (R)-BINAP is used as a chiral diphosphine ligand in asymmetric catalysis. It reacts with allylpalladium(II) chloride dimer to form a BINAP-palladium catalyst, which can catalyze the asymmetric allylation of 1,3-diketones to form chiral 2,2-dialkyl-1,3-diketones. As a chiral chelating ligand, it is used in hydrogenation reactions with very high enantiomeric excesses. |
| ln Vivo |
In vivo activity data for (R)-BINAP are not available, as the compound is a ligand used for catalysis. It is not intended for in vivo administration and has no established in vivo pharmacokinetic or pharmacodynamic profile. The compound is not designed for therapeutic use.
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| Enzyme Assay |
For in vitro catalytic reactions, (R)-BINAP is used as a chiral ligand in asymmetric catalysis. Standard protocols involve combining the ligand with a metal precursor (e.g., [Pd(allyl)Cl]₂, RuCl₂(p-cymene)₂) in an appropriate solvent to form the active catalyst. The catalyst is then used in asymmetric transformations such as hydrogenation, allylation, and other C-C bond forming reactions. The ligand's axial chirality induces enantioselectivity in the products.
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| Cell Assay |
For in vitro cell-based experiments, (R)-BINAP is not typically used directly in cell culture. It is a chemical reagent used for organic synthesis and catalysis. The compound may be used in the synthesis of chiral compounds that are subsequently tested in cell-based assays, but it is not added directly to cell cultures as a test compound.
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| Animal Protocol |
In vivo animal studies for (R)-BINAP are not applicable, as the compound is a ligand used for catalysis. No animal studies have been conducted for this compound as a therapeutic agent, and it is not intended for diagnostic or therapeutic use in animals or humans.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for (R)-BINAP are not available, as the compound is not a drug and is not administered to living organisms. The compound has a molecular weight of 622.67 g/mol and is highly lipophilic. As a large phosphine ligand, it would be expected to have poor oral bioavailability. The compound is primarily used as a reagent rather than as a drug candidate.
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| Toxicity/Toxicokinetics |
(R)-BINAP is a research chemical and should be handled with appropriate laboratory safety precautions. As a phosphine ligand, it may cause skin and eye irritation. The compound is for research use only and not for human therapeutic or diagnostic applications. Specific LD₅₀ values, acute toxicity classifications, and chronic toxicity data are not available in the public literature. Standard safety practices include the use of personal protective equipment and working in a fume hood.
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| Additional Infomation |
(R)-BINAP ((R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl) (CAS 76189-55-4) is primarily a research-grade chiral ligand, not an FDA-approved pharmaceutical drug. Its primary applications are as a chiral chelating ligand in asymmetric catalysis for hydrogenation and other reactions, and as a biochemical reagent for biomedical research. No clinical trials or approved therapeutic indications exist for this compound.
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| Molecular Formula |
C44H32P2
|
|---|---|
| Molecular Weight |
622.67
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| Exact Mass |
622.197
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| CAS # |
76189-55-4
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| Related CAS # |
(Rac)-BINAP;98327-87-8;(S)-BINAP;76189-56-5
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| PubChem CID |
634876
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| Appearance |
White to off-white solid powder
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| Boiling Point |
724.3±55.0 °C at 760 mmHg
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| Melting Point |
283-286 °C(lit.)
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| Flash Point |
419.0±37.8 °C
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| Vapour Pressure |
0.0±2.3 mmHg at 25°C
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| Index of Refraction |
235 ° (C=0.3, Toluene)
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| LogP |
13.38
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
46
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| Complexity |
797
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[C@@]1([C@]2=C3C=CC=CC3=CC=C2P(C4=CC=CC=C4)C5=CC=CC=C5)=C6C=CC=CC6=CC=C1P(C7=CC=CC=C7)C8=CC=CC=C8
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| InChi Key |
MUALRAIOVNYAIW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H
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| Chemical Name |
[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 5 mg/mL (8.03 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.5 mg/mL (0.80 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6060 mL | 8.0299 mL | 16.0599 mL | |
| 5 mM | 0.3212 mL | 1.6060 mL | 3.2120 mL | |
| 10 mM | 0.1606 mL | 0.8030 mL | 1.6060 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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