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

Base Information

• Chemical Name: 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate
• CAS No.: 35193-64-7
• Molecular Formula: C20H13O4P
• Molecular Weight: 348.295
• Hs Code.: HOSPHATE PRODUCT IDENTIFICATION
• 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: 35193-64-7.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 light yellow crystal powde
• Melting Point: ≥300 °C
• Refractive Index: 595 ° (C=1, MeOH)
• Boiling Point: 619.5 °C at 760 mmHg
• PKA: 1.14±0.20(Predicted)
• Flash Point: 328.5 °C
• PSA: 65.57000
• Density: 1.49 g/cm³
• LogP: 3.34920
• Storage Temp.: Refrigerator
• Solubility.: Soluble in DMSO and methanol (hot).
• 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:

99% ^*data from raw suppliers

(S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate >97.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• 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

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)O
• Uses: The S enantiomer of binaphthol derivative as chiral quenching agent. Used as a chiral Bronsted acid catalyst in the enantoselective Mannich reaction.

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

There total 23 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: 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

Reference yield: 56.0%

(R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-1,1'-binaphthyl-2,2'-phosphoric acid (35193-63-6,35193-64-7,39648-67-4,50574-52-2)

Guidance literature:

(R)-1,1'-Bi-2-naphthol; With pyridine; trichlorophosphate; at 20 ℃;

With water; at 20 ℃; Further stages.;

DOI:10.1021/ja0684803

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:

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

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

Refernces

• 1、 Nagaki, Aiichiro,Tamaki, Takashi. "Flash production of organophosphorus compounds in flow". supporting information. . Retrieved 2021/09/09.
• 2、 Yu, Jeongjae,Armstrong, Daniel W.,Ryoo, Jae Jeong. "Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations". . p. 74 - 84. Retrieved 2017/12/26.