Cas no 874948-59-1 ((S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate)

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate is a chiral phosphoric acid derivative widely used as an asymmetric organocatalyst in enantioselective synthesis. Its rigid binaphthyl backbone and strategically positioned phenyl groups enhance steric and electronic control, enabling high stereoselectivity in reactions such as Friedel-Crafts alkylations, Mannich-type additions, and transfer hydrogenations. The compound’s strong Br?nsted acidity and well-defined chiral environment make it particularly effective for activating imines and other electrophiles. Its stability under various reaction conditions and recoverability further contribute to its utility in synthetic chemistry. This catalyst is valued for its ability to deliver high enantiomeric excesses in diverse transformations, supporting advancements in pharmaceutical and fine chemical synthesis.
(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate structure
874948-59-1 structure
Product Name:(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
CAS No:874948-59-1
MF:C32H21O4P
MW:500.480509519577
MDL:MFCD17676194
CID:2360872
Update Time:2025-07-10

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Chemical and Physical Properties

Names and Identifiers

    • (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
    • (11bS)-4-Hydroxy-2,6-diphenyl-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
    • S-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
    • (S)-2,2′-Dihydroxy-3,3′-diphenyl-1,1′-binaphthalene cyclic phosphate
    • MDL： MFCD17676194
    • Inchi： 1S/C32H21O4P/c33-37(34)35-31-27(21-11-3-1-4-12-21)19-23-15-7-9-17-25(23)29(31)30-26-18-10-8-16-24(26)20-28(32(30)36-37)22-13-5-2-6-14-22/h1-20H,(H,33,34)
    • InChI Key： RLPAIZCRXBEKDM-UHFFFAOYSA-N
    • SMILES： O=P1(OC2C(C3C=CC=CC=3)=CC3C(C=2C2C(=C(C4C=CC=CC=4)C=C4C=2C=CC=C4)O1)=CC=CC=3)O

Experimental Properties

  • Boiling Point: 755.1°C at 760 mmHg

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Security Information

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Pricemore >>

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abcr
AB491455-100 mg
(11bS)-4-Hydroxy-2,6-diphenyl-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%, (99% ee); .
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(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt → 120 °C; 18 h, 120 °C; 120 °C → rt
1.2 Solvents: Water ;  rt → 103 °C; 3 h, 103 °C; 103 °C → rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
Chromopynones are pseudo natural product glucose uptake inhibitors targeting glucose transporters GLUT-1 and -3
Karageorgis, George ; et al, Nature Chemistry, 2018, 10(11), 1103-1111

Production Method 2

Reaction Conditions
1.1 Reagents: Butyllithium ,  N,N,N′,N′-Tetramethylethylenediamine Solvents: Diethyl ether ,  Hexane ;  30 min, rt
1.2 3 h, rt; rt → -78 °C
1.3 Reagents: Triethyl borate ;  10 min, -78 °C; -78 °C → rt; overnight, rt; rt → 0 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  0 °C → rt; 2 h, rt
2.1 Reagents: Barium hydroxide Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ,  Water ;  24 h, reflux; reflux → rt
3.1 Reagents: Boron tribromide Solvents: Dichloromethane ;  10 min, 0 °C; 18 h, rt; rt → 0 °C
3.2 Reagents: Water ;  0 °C
4.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt; 3 h, 90 °C; 90 °C → 55 °C
4.2 Reagents: Water ;  55 °C; 1 h, reflux; reflux → 60 °C
4.3 Reagents: Hydrochloric acid Solvents: Water ;  rt
4.4 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; cooled
Reference
Practical Synthesis of Chiral Phosphorous Acids Based on BINOL-Skeleton
Yan, Lin-Jie; et al, Organic Preparations and Procedures International, 2013, 45(6), 473-482

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  36 h, reflux
2.1 Reagents: Butyllithium ,  N,N,N′,N′-Tetramethylethylenediamine Solvents: Diethyl ether ,  Hexane ;  30 min, rt
2.2 3 h, rt; rt → -78 °C
2.3 Reagents: Triethyl borate ;  10 min, -78 °C; -78 °C → rt; overnight, rt; rt → 0 °C
2.4 Reagents: Hydrochloric acid Solvents: Water ;  0 °C → rt; 2 h, rt
3.1 Reagents: Barium hydroxide Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ,  Water ;  24 h, reflux; reflux → rt
4.1 Reagents: Boron tribromide Solvents: Dichloromethane ;  10 min, 0 °C; 18 h, rt; rt → 0 °C
4.2 Reagents: Water ;  0 °C
5.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt; 3 h, 90 °C; 90 °C → 55 °C
5.2 Reagents: Water ;  55 °C; 1 h, reflux; reflux → 60 °C
5.3 Reagents: Hydrochloric acid Solvents: Water ;  rt
5.4 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; cooled
Reference
Practical Synthesis of Chiral Phosphorous Acids Based on BINOL-Skeleton
Yan, Lin-Jie; et al, Organic Preparations and Procedures International, 2013, 45(6), 473-482

Production Method 4

Reaction Conditions
1.1 Reagents: Bromine Solvents: Dichloromethane ;  0 °C; 1 h, 0 °C
1.2 Reagents: Sodium bisulfite Solvents: Water ;  1 h, rt
1.3 Reagents: Potassium fluoride Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: Tetrahydrofuran ;  18 h, reflux; reflux → rt
1.4 Reagents: Boron tribromide Solvents: Dichloromethane ;  1 h, 0 °C; 0 °C → rt; 1 h, rt
1.5 Solvents: Water ;  rt
1.6 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  5 h, rt
1.7 Solvents: Water ;  30 min, rt
1.8 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  Water ;  rt
Reference
Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines
Evans, Christopher G.; et al, Organic Letters, 2009, 11(14), 2957-2959

Production Method 5

Reaction Conditions
1.1 Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Diethyl ether ,  Cyclopentyl methyl ether ;  10 min, rt; rt → 37 °C; 23 h, 37 °C; 37 °C → rt; rt → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
1.3 Reagents: Boron tribromide Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 18 h, rt; rt → 0 °C
1.4 Solvents: Water ;  1 h, rt
2.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt → 120 °C; 18 h, 120 °C; 120 °C → rt
2.2 Solvents: Water ;  rt → 103 °C; 3 h, 103 °C; 103 °C → rt
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
Chromopynones are pseudo natural product glucose uptake inhibitors targeting glucose transporters GLUT-1 and -3
Karageorgis, George ; et al, Nature Chemistry, 2018, 10(11), 1103-1111

Production Method 6

Reaction Conditions
1.1 Reagents: Boron tribromide Solvents: Dichloromethane ;  10 min, 0 °C; 18 h, rt; rt → 0 °C
1.2 Reagents: Water ;  0 °C
2.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt; 3 h, 90 °C; 90 °C → 55 °C
2.2 Reagents: Water ;  55 °C; 1 h, reflux; reflux → 60 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  rt
2.4 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; cooled
Reference
Practical Synthesis of Chiral Phosphorous Acids Based on BINOL-Skeleton
Yan, Lin-Jie; et al, Organic Preparations and Procedures International, 2013, 45(6), 473-482

Production Method 7

Reaction Conditions
1.1 Reagents: Barium hydroxide Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ,  Water ;  24 h, reflux; reflux → rt
2.1 Reagents: Boron tribromide Solvents: Dichloromethane ;  10 min, 0 °C; 18 h, rt; rt → 0 °C
2.2 Reagents: Water ;  0 °C
3.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt; 3 h, 90 °C; 90 °C → 55 °C
3.2 Reagents: Water ;  55 °C; 1 h, reflux; reflux → 60 °C
3.3 Reagents: Hydrochloric acid Solvents: Water ;  rt
3.4 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; cooled
Reference
Practical Synthesis of Chiral Phosphorous Acids Based on BINOL-Skeleton
Yan, Lin-Jie; et al, Organic Preparations and Procedures International, 2013, 45(6), 473-482

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  rt → 83 °C; 18 h, 83 °C
2.1 Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Diethyl ether ,  Cyclopentyl methyl ether ;  10 min, rt; rt → 37 °C; 23 h, 37 °C; 37 °C → rt; rt → 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
2.3 Reagents: Boron tribromide Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 18 h, rt; rt → 0 °C
2.4 Solvents: Water ;  1 h, rt
3.1 Reagents: Phosphorus oxychloride Solvents: Pyridine ;  rt → 120 °C; 18 h, 120 °C; 120 °C → rt
3.2 Solvents: Water ;  rt → 103 °C; 3 h, 103 °C; 103 °C → rt
3.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
Chromopynones are pseudo natural product glucose uptake inhibitors targeting glucose transporters GLUT-1 and -3
Karageorgis, George ; et al, Nature Chemistry, 2018, 10(11), 1103-1111

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Raw materials

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Preparation Products

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(CAS:874948-59-1)(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
Order Number:A915804
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Quantity:1g/5g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 12:57
Price ($):212.0/1057.0

(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Related Literature

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Additional information on (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate

Research Brief on (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (CAS: 874948-59-1)

In recent years, the compound (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (CAS: 874948-59-1) has garnered significant attention in the field of chemical biology and pharmaceutical research. This chiral binaphthyl derivative is widely recognized for its role as a versatile ligand and catalyst in asymmetric synthesis, as well as its potential applications in drug development and material science. The unique structural features of this compound, including its axial chirality and hydrogenphosphate functionality, make it a valuable tool for enantioselective transformations and molecular recognition.

Recent studies have focused on the synthesis and optimization of (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate to enhance its catalytic efficiency and selectivity. Advanced spectroscopic techniques, such as NMR and X-ray crystallography, have been employed to elucidate its molecular structure and interactions with various substrates. These investigations have revealed that the hydrogenphosphate group plays a critical role in stabilizing transition states during catalytic cycles, thereby improving reaction yields and enantiomeric excess.

One of the most notable applications of this compound is in the field of asymmetric organocatalysis, where it has been utilized to facilitate a range of C-C and C-X bond-forming reactions. For instance, a 2023 study demonstrated its efficacy in the enantioselective synthesis of biologically active molecules, such as β-amino acids and heterocyclic compounds. The high enantioselectivity (up to 99% ee) achieved in these reactions underscores the potential of (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate as a key building block in pharmaceutical synthesis.

In addition to its catalytic applications, this compound has also been explored for its role in drug delivery systems. Its ability to form stable complexes with metal ions and bioactive molecules has been leveraged to design targeted delivery platforms. Recent in vitro studies have shown that (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate can enhance the solubility and bioavailability of poorly water-soluble drugs, making it a promising candidate for improving therapeutic efficacy.

Despite these advancements, challenges remain in scaling up the synthesis of (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate for industrial applications. Current research efforts are directed toward developing more cost-effective and environmentally friendly synthetic routes. For example, a 2024 study reported a green chemistry approach using biocatalysts to produce this compound with reduced waste and energy consumption.

In conclusion, (S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (CAS: 874948-59-1) represents a pivotal molecule in modern chemical biology and pharmaceutical research. Its diverse applications in asymmetric synthesis, drug delivery, and material science highlight its versatility and potential for future innovations. Ongoing research aims to address existing limitations and expand its utility in both academic and industrial settings.

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Amadis Chemical Company Limited
(CAS:874948-59-1)(S)-3,3'-Bis(phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
A915804
Purity:99%/99%
Quantity:1g/5g
Price ($):212.0/1057.0
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