(S)-BINAP
Based on 1 Customer Validation
(S)-BINAP is an isomer of (R)-BINAP (HY-W017757), as well as a chiral chelating diphosphine ligand and enantioselective catalyst precursor. (S)-BINAP acts as a bidentate ligand, transferring chiral information via its binaphthyl backbone to achieve stereodiscrimination of substrates. (S)-BINAP is used for the enantioselective hydrogenation of prochiral carboxylic acids, N-acyltetrahydroisoquinolines, allylic alcohols, functionalized ketones, cyclic anhydrides, and styrenes.
For research use only. We do not sell to patients.
- Purity: 99.71%
- CAS No.: 76189-56-5
- Formula: C44H32P2
- Molecular Weight:622.67
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Storage:
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Biological Activity
|
Cell Line
|
Type | Value | Description | References |
|---|---|---|---|---|
| Hep 3B2 | IC50 |
>50 μg/mL
Compound: (S)-1, BINAP
|
Cytotoxicity against human Hep3B cells after 48 hrs by SRB assay
Cytotoxicity against human Hep3B cells after 48 hrs by SRB assay
|
[PMID: 20832917] |
(S)-BINAP can serve as a chiral ligand in Ru (II) dicarboxylate complexes to catalyze the asymmetric hydrogenation of prochiral α,β- or β,γ-unsaturated carboxylic acids, yielding optically active saturated carboxylic acids and lactones[1].
(S)-BINAP, as a chiral ligand in Rh (I) cationic complexes, catalyzes the enantioselective isomerization of N,N-diethylgeranylamine (compound 63) and N,N-diethylnerylamine (compound 64) to produce (R)-citronellal (E)-enamine (compound 65) and (S)-citronellal (E)-enamine (compound 65)[1], respectively.
(S)-BINAP acts as a chiral ligand to catalyze the asymmetric hydrogenation of N-acyl-(Z)-1-alkylidene-1,2,3,4-tetrahydroisoquinoline and γ-chloro β-keto ester 42[1].
(S)-BINAP can form [(S)-RuCl ((S)-BINAP)(C6H6)]Cl [(S)-5a] and [(S)-RuCl ((S)-BINAP)(C6H6)]BF4 [(S)-5d][2].
(S)-BINAP-derived catalyst [(S)-RuI ((S)-BINAP)(p-cymene)]I [(S)-10c] catalyzes the asymmetric hydrogenation of methyl (±)-2-(benzamidomethyl)-3-oxobutanoate [(±)-16] to produce syn-(2R,3S)-17; it catalyzes the asymmetric hydrogenation of methyl pyruvate to produce (S)-methyl 2-lactate; it catalyzes the asymmetric hydrogenation of methyl 3-oxobutanoate to produce (S)-methyl 3-hydroxybutanoate; and it catalyzes the asymmetric hydrogenation of geraniol to produce (R)-citronellol[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 76189-56-5
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Appearance Solid
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Molecular Weight 622.67
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Formula C44H32P2
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Color White to off-white
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SMILES
C1(C=CC=C2)=C2[C@@]([C@@]3=C(C=CC=C4)C4=CC=C3P(C5=CC=CC=C5)C6=CC=CC=C6)=C(P(C7=CC=CC=C7)C8=CC=CC=C8)C=C1
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Solvent & Solubility
DMSO : 2 mg/mL (3.21 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (284 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.6060 mL | 8.0299 mL | 16.0599 mL | 40.1497 mL |