![(R)-[1,1'-Binaphthalene]-2,2'-diamine (R-(-)-2,2-Diamino-1,1-binaphthyl)](/upload/1124/V64616.png)
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| Targets |
(R)-[1,1'-Binaphthalene]-2,2'-diamine itself does not have a defined biological target, as it is a chemical reagent rather than a pharmacologically active compound. However, when used as a ligand in metal-catalyzed reactions, its targets are transition metal centers such as palladium, ruthenium, or copper, forming chiral complexes that facilitate asymmetric transformations. The binaphthyl backbone provides axial chirality that induces enantioselectivity in catalytic processes. Its primary function is to impart chirality to synthetic intermediates and final drug candidates.
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| ln Vitro |
As a chemical reagent, (R)-[1,1'-Binaphthalene]-2,2'-diamine exhibits no intrinsic pharmacological activity in vitro. Its utility lies in its ability to act as a chiral inducer in asymmetric synthesis. It is used in the synthesis of sterically hindered binaphthalene-based monophosphane ligands and other chiral catalysts. The compound is also employed in the preparation of chiral stationary phases for HPLC and in the synthesis of optically active compounds for biomedical research. It is not evaluated in cell-based assays for biological activity.
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| ln Vivo |
(R)-[1,1'-Binaphthalene]-2,2'-diamine does not possess in vivo biological activity, as it is not designed for therapeutic use. The compound is a synthetic intermediate and chiral ligand intended for laboratory research only. No pharmacological effects have been reported for this compound in animal models. When used in the synthesis of drug candidates, the final products—not the ligand itself—are evaluated for in vivo activity. The compound is not administered to animals as a test article in standard pharmacological studies.
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| Enzyme Assay |
In vitro assays for (R)-[1,1'-Binaphthalene]-2,2'-diamine are not applicable, as this compound is not a biologically active agent. When employed as a chiral ligand, a typical experimental protocol involves dissolving the compound in an appropriate organic solvent (e.g., dichloromethane, toluene, or THF) and mixing it with a metal precursor such as [PdCl₂(CH₃CN)₂] or [RuCl₂(p-cymene)]₂ to form the chiral catalyst. The catalyst is then used to promote asymmetric reactions. For quality control, enantiomeric purity is assessed by chiral HPLC or by measuring optical rotation.
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| Cell Assay |
In vitro cell culture experiments with (R)-[1,1'-Binaphthalene]-2,2'-diamine are not standard, as the compound is not a cell-permeable bioactive molecule. If cellular studies are conducted, the compound is typically dissolved in DMSO and added to cell culture media at micromolar concentrations to assess potential cytotoxicity. However, due to its hydrophobic nature, it may precipitate in aqueous media. Standard cytotoxicity assays such as MTT can be used, but the compound is generally not evaluated in cellular systems as it is not intended to have biological activity.
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| Animal Protocol |
In vivo animal experiments with (R)-[1,1'-Binaphthalene]-2,2'-diamine are not conducted, as the compound is a laboratory reagent rather than a test article. When used to synthesize pharmacologically active agents, those final drug candidates are subjected to animal studies following standard protocols: oral or intravenous administration, blood sampling for pharmacokinetic analysis, tissue collection for biodistribution studies, and histopathological examination for toxicity assessment. The ligand itself is not evaluated in vivo.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (R)-[1,1'-Binaphthalene]-2,2'-diamine are not characterized, as it is not a drug substance. Based on its physicochemical properties (molecular weight 284.36, high lipophilicity, low water solubility), the compound is expected to have poor oral bioavailability. It is likely to be metabolized by cytochrome P450 enzymes if absorbed, with potential formation of oxidative and conjugative metabolites. The compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Toxicological data for (R)-[1,1'-Binaphthalene]-2,2'-diamine are limited, as it is a research reagent. The compound contains an aromatic amine functional group, which is a structural alert for potential mutagenicity and carcinogenicity. Standard laboratory precautions should be followed, including the use of gloves, safety glasses, and fume hoods when handling. The compound should be stored protected from light and moisture. No acute toxicity data are available. It is not intended for drug, household, or other uses.
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| References |
[1]. Singh AV, et al. PR-924, a selective inhibitor of the immunoproteasome subunit LMP-7, blocks multiple myeloma cell growth both in vitro and in vivo. Br J Haematol. 2011 Jan;152(2):155-63.
[2]. Parlati F, et al. Carfilzomib can induce tumor cell death through selective inhibition of the chymotrypsin-like activity of the proteasome. Blood. 2009 Oct 15;114(16):3439-47. |
| Additional Infomation |
(R)-[1,1'-Binaphthalene]-2,2'-diamine is widely used as a chiral building block in asymmetric catalysis and the synthesis of chiral auxiliaries. It is one of the most important chiral diamines derived from binaphthyl, alongside its (S)-enantiomer (CAS 18531-95-8) and the racemic mixture. The compound is used in the preparation of BINAM-derived ligands and catalysts for enantioselective transformations. It has applications in the synthesis of chiral pharmaceutical intermediates, agrochemicals, and functional materials. It has not undergone clinical trials and is not approved as a drug.
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| Molecular Formula |
C20H16N2
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| Molecular Weight |
284.35
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| Exact Mass |
284.131
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| CAS # |
18741-85-0
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| Related CAS # |
(S)-[1,1'-Binaphthalene]-2,2'-diamine;18531-95-8;1,1'-Binaphthyl-2,2'-diamine;4488-22-6
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| PubChem CID |
20571
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| Appearance |
White to light brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
480.8±30.0 °C at 760 mmHg
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| Melting Point |
242-244 °C(lit.)
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| Flash Point |
293.9±24.0 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.775
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| LogP |
3.85
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
22
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| Complexity |
346
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| Defined Atom Stereocenter Count |
0
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| SMILES |
NC1=CC=C2C=CC=CC2=[C@@]1[C@@]3=C4C=CC=CC4=CC=C3N
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| InChi Key |
DDAPSNKEOHDLKB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H16N2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12H,21-22H2
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| Chemical Name |
1-(2-aminonaphthalen-1-yl)naphthalen-2-amine
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5168 mL | 17.5840 mL | 35.1679 mL | |
| 5 mM | 0.7034 mL | 3.5168 mL | 7.0336 mL | |
| 10 mM | 0.3517 mL | 1.7584 mL | 3.5168 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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