1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

Base Information

• Chemical Name: 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate
• CAS No.: 35193-63-6
• Molecular Formula: C₂₀H₁₃O₄P
• Molecular Weight: 348.295
• Hs Code.: 2931499090
• European Community (EC) Number: 609-734-1,252-425-8,609-088-0
• NSC Number: 244999
• DSSTox Substance ID: DTXSID50188685
• Nikkaji Number: J1.155.688D,J2.866.066I,J283.276C,J283.277A,J289.928K,J413.364A,J413.925I,J254.896H,J260.563E,J27.175F
• Wikidata: Q72443546
• Mol file: 35193-63-6.mol

Synonyms:1,1'-binaphthyl-2,2'-diyl hydrogen phosphate;1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, (+-)-isomer;1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, (R)-isomer;1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, (S)-isomer;1,1'-binaphthyl-2,2'-diylhydrogenphosphate;BDHP cpd

Chemical Property of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

Chemical Property:

• Appearance/Colour: WHITE TO OFF-WHITE POWDER, CRYSTALS, CRYSTALLINE POWDER AND/OR CHUNKS
• Melting Point: ≥300 °C
• Boiling Point: 619.5 °C at 760 mmHg
• PKA: 1.14±0.20(Predicted)
• Flash Point: 328.5 °C
• PSA: 65.57000
• Density: 1.493 g/cm³
• LogP: 5.53160
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Extremely low soluble in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 348.05514589
• Heavy Atom Count: 25
• Complexity: 508

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+/-)-1,1'-Binaphthyl-2,2'-diyl Hydrogenphosphate >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)O
• 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.

Technology Process of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

There total 22 articles about 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,1'-bi-2-naphthol (602-09-5) → 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (35193-63-6,35193-64-7,39648-67-4,50574-52-2)

Guidance literature:

With pyridine; trichlorophosphate; at 20 ℃; for 1h;

Reference yield: 94.0%

(4S,5S)-2,2-Dimethyl-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-(S)-1,1'-bi-2,2'-naphthylhydrogenphosphat → (S)-(+)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (35193-63-6,35193-64-7,39648-67-4,50574-52-2)

Guidance literature:

With hydrogenchloride; In water; at 95 ℃; for 0.166667h;

Reference yield: 90.0%

(S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (35193-63-6,35193-64-7,39648-67-4,50574-52-2)

Guidance literature:

With pyridine; trichlorophosphate; at 20 - 60 ℃;

DOI:10.1002/chem.200900210

upstream raw materials:

(R)-1,1'-binaphthalene-2,2'-diyl phosphoric acid chloride

1,1'-bi-2-naphthol

(+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate

(R)-1,1'-Bi-2-naphthol

Downstream raw materials:

(+)-2,2'-dihydroxy-1,1'-binaphthyl

(R)-1,1'-binaphthyl-2,2'-phosphoric acid

(S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

(+)-Tamsulosin

Refernces

• 1、 -. "FUSED RING PYRIMIDONE DERIVATIVES FOR USE IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES". Page/Page column 100-101; 125; 127; 230-232; 239-240; 279-280. . Retrieved 2022/04/03.
• 2、 Carden, Jamie L.,Melen, Rebecca L.,Newman, Paul D.,Ruddy, Adam J.,Willcox, Darren. "Asymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands". supporting information. p. 2417 - 2420. Retrieved 2020/03/05.