35193-63-6

Basic information

• Product Name: 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate
• Synonyms: (+/-)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL HYDROGENPHOSPHATE;2-HYDROXY-2LAMBDA5-DINAPHTHO[2,1-D:1,2-F][1,3,2]DIOXAPHOSPHEPIN-2-ONE;(+/-)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGENPHOSPHATE;1,1'-BINAPHTHYL-2,2'-DIYL HYDROGENPHOSPHATE;4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide;(R)-(-)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL HYDROGENPHOSPHATE;(R)-4-HYDROXY DINAPHTHO[2,1-D:1',2'-F][1,3,2]-DIOXAPHOSPHEPIN-4-OXID;(R)-4-HYDROXYDINAPHTHO[2,1-D:1',2'-F][1,3,2]DIOXAPHOSPHEPIN-4-OXIDE
• CAS NO: 35193-63-6
• Molecular Formula: C₂₀H₁₃O₄P
• Molecular Weight: 348.29
• EINECS: 252-425-8
• Product Categories: chiral;Phosphorus Catalysts;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Achiral Phosphine;Aryl Phosphine
• Mol File: 35193-63-6.mol
• Article Data: 27

Chemical Properties

• Melting Point: ≥300 °C
• Boiling Point: 619.5 °C at 760 mmHg
• Flash Point: 328.5 °C
• Appearance: /Solid
• Density: 1.493 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.14±0.20(Predicted)
• Water Solubility: Extremely low soluble in water.
• CAS DataBase Reference: 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate(35193-63-6)
• EPA Substance Registry System: 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate(35193-63-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 3
• RTECS: RZ2475100
• F: 10-23
• Hazardous Substances Data: 35193-63-6(Hazardous Substances Data)

Usage

Description

1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is a white to light yellow crystalline powder that serves as a chiral chemical compound and a chiral ligand in various chemical reactions. It is known for its ability to complex with rhodium and mediate the asymmetric dipolar cycloaddition of diazo compounds, making it a valuable tool in the field of asymmetric synthesis.

Uses

Used in Asymmetric Synthesis:
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand for hydrocarboxylation reactions, facilitating the formation of chiral molecules with a specific configuration. This is particularly important in the pharmaceutical industry, where the stereochemistry of a molecule can significantly impact its biological activity and efficacy.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand for the resolution of racemic amines, which are often difficult to separate. The use of this chiral acid allows for the production of enantiomerically pure compounds, which can be crucial for the development of effective and safe drugs.
Used in Catalyst Development:
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is also used in the development of catalysts for asymmetric hydrocarboxylations and dipolar cycloadditions. Palladium and rhodium derivatives of this compound have been employed to improve the selectivity and efficiency of these reactions, leading to the synthesis of complex molecules with high enantiomeric purity.
Overall, 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is a versatile and valuable compound in the fields of asymmetric synthesis, pharmaceuticals, and catalyst development, playing a crucial role in the production of enantiomerically pure compounds and the development of efficient catalytic systems.

Upstream product

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 124583-86-4 (R)-1,1'-binaphthalene-2,2'-diyl phosphoric acid chloride 
• 602-09-5 1,1'-bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 35193-63-6 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 7647-01-0 hydrogenchloride 
• 124583-86-4 (+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate 

Downstream Products

• 35193-63-6 (R)-1,1'-binaphthyl-2,2'-phosphoric acid 
• 35193-63-6 (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate 

Relevant articles and documents

Hydrophilic interior between hydrophobic regions in inverse bilayer structures of cation-1,1′-binaphthalene-2,2′-diyl phosphate salts

A series of 1,1′-binaphthalene-2,2′-diyl phosphate (BNPPA -) salts have been synthesized. Their crystal packings show a separation of the hydrophobic naphthyl and hydrophilic (RO)2PO 2- phosphate/cation/solvate regions. Hydrogen bonding in the latter is the driving force for "inverse bilayer" formation, with a hydrophilic interior exposing the hydrophobic binaphthyl groups to the exterior. Stacking of the inverse bilayers occurs less through π-π and more through CH...π interactions between the naphthyl groups, which correlates with the formation of thin crystal plates along the stacking direction. Cations used with R- or rac-BNPPA- are protonated isonicotin-1-ium amide (1), isonicotin-1-ium acid (2), guanidinium (3), the metal complexes trans-tetraammine-dimethanol-copper(II) (4), trans-diaqua-tetramethanol-copper(II) (5) and cis-diaqua-bis(ethylene diamine)-nickel(II) (6). Crystallization occurs with inclusion of water and methanol solvent molecules, except in 2. Starting from R-BNPPA, inversion takes place with calcium acetate to give 1 as the racemate. 2 is crystallized as the R-BNPPA salt. The inversion-symmetrical complex trans-[Cu(H2O) 2(CH3OH)4]2+ in 5 has Cu-OH 2 bond lengths of 1.937(4) A, and Cu-O(methanol) of 2.112(4) and 2.167(4) A, corresponding to a compressed tetragonal geometry. the Royal Society of Chemistry the Centre National de la Recherche Scientifique 2006.

Flash production of organophosphorus compounds in flow

Flow synthesis techniques have received a significant amount of attention due to their high productivity. However, when reaction condition is heterogeneous, it is usually difficult to adapt it to flow synthesis. Herein, by selecting appropriate reagents, the synthesis of phosphate esters, which is commonly heterogeneous, was made homogeneous, enabling synthesis in flow systems. In addition, reaction rate was accelerated compared to the batch system. It was demonstrated that not only can the high productivity of flow synthesis be achieved in flow, but also high productivity can be achieved by accelerating the reaction. Finally, we demonstrated the synthesis of the Akiyama-Terada catalyst, a chiral organocatalysts, in a short period.

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).