(R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate

Base Information

• Chemical Name: (R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate
• CAS No.: 39648-67-4
• Molecular Formula: C₂₀H₁₃O₄P
• Molecular Weight: 348.295
• Hs Code.: HOSPHATE PRODUCT IDENTIFICATION
• European Community (EC) Number: 609-734-1
• DSSTox Substance ID: DTXSID70960268
• Nikkaji Number: J1.597.580F,J935.811K
• Wikidata: Q72443550
• Mol file: 39648-67-4.mol

Synonyms:EC 609-734-1;13-Oxido-12,14-dioxa-13lambda5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 13-oxide;(R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate;DTXSID70960268;[1,1'-Binaphthalene-2,2'-diylbis(oxy)]phosphinic acidanion;4-Oxylatodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide;4-Oxo-4H-4lambda~5~-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-olate

Chemical Property of (R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate

Chemical Property:

• Appearance/Colour: off-white powder
• 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: 5.53160
• Storage Temp.: Refrigerator
• Solubility.: Solubility in hot Methanol, almost transparency.
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 347.04732086
• Heavy Atom Count: 25
• Complexity: 500

Purity/Quality:

98%,Pd>21.5% ^*data from raw suppliers

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate >98.0%(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: chiral ligand for hydroxycarboxylations, complexes rhodium The R enantiomer of binaphthol derivative as chiral quenching agent. 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 (R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate

There total 22 articles about (R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate 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:

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

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

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

(+)-Tamsulosin

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.