![N-Benzylcinchonidinium chloride (N-benzylcinchonidinium chloride [chiral phase transfer catalyst])](/upload/1124/V66277.png)
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| Other Sizes |
| Targets |
There is no biological target for this compound. It is a chemical catalyst that facilitates the transfer of anionic reactants (e.g., enolates) from an aqueous phase to an organic phase, while the chiral cinchonidinium moiety induces stereoselectivity in the product.
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| ln Vitro |
No in vitro biological activity is reported. In synthetic chemistry, its catalytic activity is measured by reaction yield (typically >80%) and enantiomeric excess (ee, often 80-99% ee) in model reactions such as the asymmetric alkylation of glycine imines to produce chiral alpha-amino acids.
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| ln Vivo |
No in vivo activity is reported. This compound is not used in animals. Its application is exclusively in organic chemistry reaction flasks.
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| Enzyme Assay |
Not applicable. Instead, a typical catalytic protocol: To a biphasic mixture of an organic solvent (toluene or DCM) and aqueous base (e.g., 50% KOH), add the substrate (e.g., N-(diphenylmethylene)glycine tert-butyl ester) and N-Benzylcinchonidinium chloride (1-10 mol%). Stir at 0degC to room temperature, add the alkylating agent, and stir for 2-24 hours. Product is extracted and analyzed by chiral HPLC for ee.
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| Cell Assay |
No cell-based protocol exists. This compound is not used in cell culture. It may be cytotoxic due to its quaternary ammonium structure, but no specific studies are available.
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| Animal Protocol |
No in vivo animal protocol exists. It is not administered to animals. Standard chemical handling procedures for quaternary ammonium salts apply.
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| ADME/Pharmacokinetics |
PK properties are not applicable. The compound is hydrophilic due to the quaternary ammonium group and is not intended for biological use. It is stable in air and moisture but should be stored dry. Soluble in water, DMSO, and some organic solvents.
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| Toxicity/Toxicokinetics |
Toxicity: As a quaternary ammonium salt, it can be irritating to skin, eyes, and respiratory tract. The benzyl group may increase potential for sensitization. Acute toxicity data are limited, but standard precautions (gloves, goggles, fume hood) are advised. Not for human consumption.
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| Additional Infomation |
N-Benzylcinchonidinium chloride is a highly effective chiral phase-transfer catalyst for the synthesis of unnatural amino acids, chiral building blocks for pharmaceuticals (e.g., for sitagliptin). It is also used in the asymmetric synthesis of warfarin and other drugs. This product is for research use only.
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| Molecular Formula |
C26H29CLN2O
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| Molecular Weight |
420.98
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| Exact Mass |
420.196
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| CAS # |
69257-04-1
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| PubChem CID |
13095481
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| Appearance |
Off-white to pink solid powder
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| Melting Point |
210ºC (dec.)(lit.)
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| Index of Refraction |
-184 ° (C=1， H2O)
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| LogP |
1.842
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
30
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| Complexity |
573
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| Defined Atom Stereocenter Count |
2
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| SMILES |
[Cl-].O([H])[C@]([H])(C1=C([H])C([H])=NC2=C([H])C([H])=C([H])C([H])=C12)C1([H])C([H])([H])C2([H])C([H])([H])C([H])([H])[N+]1(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])C([H])([H])C2([H])C([H])=C([H])[H]
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| InChi Key |
FCHYSBWCOKEPNQ-ZTXLOYDLSA-M
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| InChi Code |
InChI=1S/C26H29N2O.ClH/c1-2-20-18-28(17-19-8-4-3-5-9-19)15-13-21(20)16-25(28)26(29)23-12-14-27-24-11-7-6-10-22(23)24;/h2-12,14,20-21,25-26,29H,1,13,15-18H2;1H/q+1;/p-1/t20?,21?,25-,26+,28?;/m0./s1
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| Chemical Name |
(R)-[(2S)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride
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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 | 2.3754 mL | 11.8770 mL | 23.7541 mL | |
| 5 mM | 0.4751 mL | 2.3754 mL | 4.7508 mL | |
| 10 mM | 0.2375 mL | 1.1877 mL | 2.3754 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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