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

Chemical Properties

white to light yellow crystal powde

Uses

1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate, is used as a chiral chemical compound, a chiral ligand used in hydrocarboxylation reactions. Complexes with rhodium and mediates the asymmetric dipolar cycloaddition of diazo compounds. A number of racemic amines which have proven difficult to separate have been resolved with this chiral acid. Palladium derivatives have been used in asymmetric hydrocarboxylations, and rhodium derivatives have been used in dipolar cycloadditions.

Upstream product

• 124583-86-4 (+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 7647-01-0 hydrogenchloride 
• 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 
• 124583-86-4 (R)-1,1'-binaphthalene-2,2'-diyl phosphoric acid chloride 

Downstream Products

• 82300-62-7 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 4-oxide 
• 18531-94-7 (+)-2,2'-dihydroxy-1,1'-binaphthyl 
• 35193-63-6 (R)-1,1'-binaphthyl-2,2'-phosphoric acid 
• 35193-63-6 (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate 
• 106463-17-6 (+)-Tamsulosin 

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).