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| Targets |
1,1'-Binaphthyl-2,2'-diamine does not have a specific biological target in the traditional pharmacological sense. It is primarily a chemical reagent and chiral ligand used in asymmetric synthesis. The compound's "target" in a research context is the transition metal center (e.g., palladium, ruthenium, rhodium) in catalytic reactions, where it coordinates as a bidentate ligand to induce chirality. The compound's nitrogen atoms are important for metal coordination and catalytic activity. It is used to synthesize chiral catalysts for asymmetric hydrogenation, C-C bond formation, and other transformations.
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| ln Vitro |
In vitro, 1,1'-Binaphthyl-2,2'-diamine is used as a chiral ligand in catalytic reactions rather than as a biologically active compound. The compound's activity is measured by its ability to induce enantioselectivity in chemical reactions. When coordinated to transition metals, it facilitates asymmetric transformations with high enantiomeric excess (ee). The compound's efficiency is evaluated by reaction yield and enantioselectivity. The compound is also used as a building block for more complex chiral ligands and organocatalysts. Some studies suggest potential anticancer activity, but this is not the primary application.
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| ln Vivo |
In vivo, 1,1'-Binaphthyl-2,2'-diamine is not used as a therapeutic agent. Its applications are exclusively in chemical synthesis and catalysis. The compound has been studied for anticancer activity in vitro, but in vivo studies are limited. As a chemical reagent, it is not administered to animals for pharmacological evaluation. The compound's in vivo behavior, if any, would be related to its use in the synthesis of pharmaceutical compounds rather than direct biological activity.
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| Enzyme Assay |
Non-cell-based assays for 1,1'-Binaphthyl-2,2'-diamine involve characterization of its chiral properties and catalytic activity. The compound's optical purity is determined by polarimetry or chiral HPLC. Its ability to serve as a chiral ligand is evaluated in model asymmetric reactions, such as asymmetric hydrogenation or allylic alkylation, where reaction yield and enantiomeric excess (ee) are measured. Coordination chemistry studies involve NMR spectroscopy and X-ray crystallography to determine the structure of metal-ligand complexes. The compound's purity and identity are confirmed by NMR, MS, and elemental analysis.
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| Cell Assay |
As a chemical reagent, 1,1'-Binaphthyl-2,2'-diamine is not used in standard cellular assays for biological activity. However, in the context of studying its potential anticancer properties, the compound may be tested on cancer cell lines. Cells are treated with the compound at various concentrations, and cell viability is measured by MTT or CellTiter-Glo assays. Apoptosis is assessed by Annexin V/PI staining. The compound's ability to inhibit cell proliferation or induce cell death is evaluated. However, these studies are limited, and the compound is primarily used as a chiral ligand rather than a bioactive compound.
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| Animal Protocol |
1,1'-Binaphthyl-2,2'-diamine is not used in animal experiments as a therapeutic agent. It is a chemical reagent used in the synthesis of pharmaceutical compounds. The compound's in vivo effects have not been systematically studied. If used in animal studies, it would be as a component of a drug formulation or as a tracer, but these applications are not standard. The compound is handled with standard laboratory safety precautions as an organic chemical.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties are not applicable to 1,1'-Binaphthyl-2,2'-diamine as it is not a therapeutic agent. The compound is used exclusively as a chemical reagent and chiral ligand in research and pharmaceutical synthesis. Its chemical stability, solubility, and handling properties are characterized for use in synthetic chemistry. The compound has limited water solubility and is typically dissolved in organic solvents for reactions. No PK data are available or relevant for this compound.
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| Toxicity/Toxicokinetics |
The toxicity of 1,1'-Binaphthyl-2,2'-diamine has not been comprehensively evaluated as it is not a therapeutic agent. As an aromatic amine compound, it should be handled with caution due to potential toxicity. Standard laboratory safety practices should be followed, including the use of gloves, lab coat, and eye protection. The compound may be irritating to skin, eyes, and respiratory tract. Comprehensive toxicological data including LD₅₀, genotoxicity, and carcinogenicity are not available. The compound is for research use only and is not intended for human consumption.
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| References |
[1]. Kettle JG, et al. Discovery of AZD4625, a Covalent Allosteric Inhibitor of the Mutant GTPase KRASG12C. J Med Chem. 2022 May 12;65(9):6940-6952.
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| Additional Infomation |
1,1'-Binaphthyl-2,2'-diamine (CAS# 4488-22-6) is an organic compound with the molecular formula C₂₀H₁₆N₂ and a molecular weight of 284.35. It is an axially dissymmetric binaphthyl ligand (BINAM) widely used as a building block for transition-metal ligands and organocatalysts in asymmetric synthesis. The compound's nitrogen atoms are important for metal coordination and catalytic activity. It is also known as [1,1'-Binaphthalene]-2,2'-diamine and is available as both racemic and enantiopure forms. The compound is primarily used in pharmaceutical research for chiral catalysis and is not approved as a therapeutic agent.
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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 # |
4488-22-6
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| Related CAS # |
(R)-[1,1'-Binaphthalene]-2,2'-diamine;18741-85-0;(S)-[1,1'-Binaphthalene]-2,2'-diamine;18531-95-8
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| PubChem CID |
20571
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| Appearance |
Off-white to light yellow 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 |
242-244ºC(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 |
N([H])([H])C1C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C2C=1C1=C(C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C12)N([H])[H]
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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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