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| Other Sizes |
| Targets |
(R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate does not have a defined pharmacological target. It is a chiral organocatalyst and ligand used in asymmetric synthesis. Its mechanism of action is chemical: it provides excellent stereocontrol in catalytic reactions, particularly in metal-catalyzed asymmetric transformations such as hydrogenations, allylic substitutions, and cycloadditions.
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| ln Vitro |
In hydrocarboxylation processes, chiral ligands such as (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate are employed. participates in asymmetric dipolar cycloadditions of diazo compounds by forming complexes with rhodium. With the help of this chiral acid, numerous racial amines that had proven challenging to separate have been resolved. Relative to rhodium, palladium derivatives have been employed in dipolar cycloaddition processes and in asymmetric hydrocarboxylation reactions. For chiral enantioselective Mannich processes, employing Bronsted acid as the catalyst.
In vitro, (R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used in a chiral Bronsted acid catalyzed enantioselective Mannich reaction. It is a chiral ligand used in hydrocarboxylation reactions and complexes with rhodium to mediate asymmetric dipolar cycloadditions of diazo compounds. It is also used to resolve racemic amines. |
| ln Vivo |
In vivo activity data for (R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate are not available, as the compound is a chiral ligand used for catalysis. It is not intended for in vivo administration and has no established in vivo pharmacokinetic or pharmacodynamic profile.
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| Enzyme Assay |
For in vitro catalytic reactions, (R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand or organocatalyst. Standard protocols involve combining the ligand with a metal precursor (e.g., rhodium, palladium) in an appropriate solvent to form the active catalyst. The catalyst is then used in asymmetric transformations such as hydrogenations or cycloadditions.
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| Cell Assay |
For in vitro cell-based experiments, (R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate 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.
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| Animal Protocol |
In vivo animal studies for (R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate 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.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for (R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate are not available, as the compound is not a drug and is not administered to living organisms. It has an optical rotation of [α]20/D −605° (c = 1.35 in methanol).
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| Toxicity/Toxicokinetics |
(R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is a research chemical and should be handled with appropriate laboratory safety precautions. It is classified as a skin irritant (Skin Irrit. 2). Standard safety practices include the use of personal protective equipment.
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| Additional Infomation |
(R)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate (CAS 39648-67-4) is primarily a research-grade chiral ligand and organocatalyst, not an FDA-approved pharmaceutical drug. Its primary applications are in asymmetric synthesis for enantioselective reactions, including hydrogenations, allylic substitutions, and cycloadditions.
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| Molecular Formula |
C20H13O4P
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|---|---|
| Molecular Weight |
348.29
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| Exact Mass |
348.055
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| CAS # |
39648-67-4
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| PubChem CID |
99589
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
619.5±38.0 °C at 760 mmHg
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| Melting Point |
>300ºC
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| Flash Point |
328.5±26.8 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.763
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| LogP |
3.99
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
25
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| Complexity |
508
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)[O-]
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| InChi Key |
JEHUZVBIUCAMRZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)
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| Chemical Name |
13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 13-oxide
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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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). 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: 100 mg/mL (287.12 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.18 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.18 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.18 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8712 mL | 14.3559 mL | 28.7117 mL | |
| 5 mM | 0.5742 mL | 2.8712 mL | 5.7423 mL | |
| 10 mM | 0.2871 mL | 1.4356 mL | 2.8712 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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