(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane
Based on 1 Customer Validation
(+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane ((S,S)-Ph-BPE) is a chiral bisphosphine ligand and catalyst. (+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane acts as a chiral ligand in rhodium-catalyzed reductive hydroformylation of alkenyl boronic esters, enabling enantiodivergent synthesis of chiral γ-boryl alcohols. (+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane forms chiral nickel-phosphine complexes to mediate asymmetric hydrogenation of aliphatic γ- and δ-keto acids; protons promote substrate C=O bond activation and stereoselectivity control via hydrogen bonding. (+)-1,2-Bis ((2S,5S)-2,5-diphenylphospholano)ethane forms a monodentate nickel complex, which serves as the active species for asymmetric hydrogenation of aliphatic keto acids.
For research use only. We do not sell to patients.
- Purity : 98.0%
- CAS No.: 824395-67-7
- Formula: C34H36P2
- Molecular Weight:506.60
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Storage:
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
Description
In Vitro
(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane ((S,S)-Ph-BPE) acts as a chiral ligand in Rh-catalyzed reductive hydroformylation of aryl-substituted alkene 1,2-diboronic esters, enabling formation of chiral 1,3-diols[1].
(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane induces enantiodivergence in Rh-catalyzed reductive hydroformylation of alkene 1,2-diboronic esters and α-substituted alkenyl boronic esters via energy differences in the enantio-determining olefin insertion transition states, producing chiral products with opposite configurations[1].
(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane (0.0133-1 mol%; 12-24 h) forms a highly active homogeneous chiral nickel-phosphine complex that catalyzes the asymmetric hydrogenation of aliphatic γ- and δ-ketoacids, including biomass-derived levulinic acid, to produce chiral lactones with up to 98% yield, 99% ee, and a maximum substrate-to-catalyst ratio of 7500[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. 824395-67-7
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Appearance Solid
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Molecular Weight 506.60
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Formula C34H36P2
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Color White to off-white
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SMILES
P1([C@H](C2=CC=CC=C2)CC[C@H]1C3=CC=CC=C3)CCP4[C@H](C5=CC=CC=C5)CC[C@H]4C6=CC=CC=C6
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Synonyms
(S,S)-Ph-BPE
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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
In Vitro:
DMSO : 25 mg/mL (49.35 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 (281 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
[1]. Yu Y, et al. Enantiodivergent Rh-Catalyzed Reductive Hydroformylation of Alkenyl Boronic Esters. Angew Chem Int Ed Engl. 2026;65(2):e20602. [Content Brief]
[2]. Deng CQ, et al. Proton-Promoted Nickel-Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids. Angew Chem Int Ed Engl. 2022;61(15):e202115983. [Content Brief]
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 | 1.9739 mL | 9.8697 mL | 19.7394 mL | 49.3486 mL |
| 5 mM | 0.3948 mL | 1.9739 mL | 3.9479 mL | 9.8697 mL | |
| 10 mM | 0.1974 mL | 0.9870 mL | 1.9739 mL | 4.9349 mL | |
| 15 mM | 0.1316 mL | 0.6580 mL | 1.3160 mL | 3.2899 mL | |
| 20 mM | 0.0987 mL | 0.4935 mL | 0.9870 mL | 2.4674 mL | |
| 25 mM | 0.0790 mL | 0.3948 mL | 0.7896 mL | 1.9739 mL | |
| 30 mM | 0.0658 mL | 0.3290 mL | 0.6580 mL | 1.6450 mL | |
| 40 mM | 0.0493 mL | 0.2467 mL | 0.4935 mL | 1.2337 mL |
(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane Related Classifications
HY-W021016 Related Classifications
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Keywords
- (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane
- 824395-67-7
- (S,S)-Ph-BPE
- Biochemical Assay Reagents
- levulinic acid
- chiral bisphosphorus ligand
- chiral γ-boryl alcohols
- rhodium
- chiral nickel-phosphine complex
- aliphatic γ-ketoacids
- alkenyl boronic esters
- asymmetric hydrogenation
- active pharmaceutical ingredients
- aliphatic δ-ketoacids
- Inhibitor
- inhibitor
- inhibit