Diethyl naphthalen-2-ylphosphonate

Base Information

• Chemical Name: Diethyl naphthalen-2-ylphosphonate
• CAS No.: 17067-93-5
• Molecular Formula: C14H17O3P
• Molecular Weight: 264.261
• DSSTox Substance ID: DTXSID201293309
• Nikkaji Number: J275.416I
• Mol file: 17067-93-5.mol

Synonyms:diethyl naphthalen-2-ylphosphonate;17067-93-5;Diethyl 2-Naphthaylphosphonate;SCHEMBL15565824;HDZBTSXGRRHMDX-UHFFFAOYSA-N;DTXSID201293309;Diethyl P-2-naphthalenylphosphonate;SY312163

Chemical Property of Diethyl naphthalen-2-ylphosphonate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 264.09153140
• Heavy Atom Count: 18
• Complexity: 295

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1=CC2=CC=CC=C2C=C1)OCC

Technology Process of Diethyl naphthalen-2-ylphosphonate

There total 3 articles about Diethyl naphthalen-2-ylphosphonate 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: 75.0%

4-chloro-2-aldehyde phenylboronic acid (913835-76-4) + diethyl (1-bromonaphthalen-2-yl)phosphonate → (-)-diethyl 1-(4-chloro-2-formylphenyl)naphthalen-2-ylphosphonate + diethyl (naphthalen-2-yl)phosphonate (17067-93-5)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-(+)-2-(dicyclohexylphosphino)-2'-methoxy-1,1'-binaphthyl; In toluene; at 50 ℃; for 72h; Overall yield = 326 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol402666p

Reference yield: 61.0%

(2-formyl-5-chlorophenyl)boronic acid (870238-36-1) + diethyl (1-bromonaphthalen-2-yl)phosphonate → (-)-diethyl 1-(5-chloro-2-formylphenyl)naphthalen-2-ylphosphonate + diethyl (naphthalen-2-yl)phosphonate (17067-93-5)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-(+)-2-(dicyclohexylphosphino)-2'-methoxy-1,1'-binaphthyl; In toluene; at 50 ℃; for 48h; Overall yield = 293 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol402666p

Reference yield:

naphthalene (91-20-3,71998-51-1,72931-45-4) + phosphonic acid diethyl ester (762-04-9) → Diethyl phosphate (598-02-7) + Tetraethyl pyrophosphate (107-49-3) + diethyl (naphthalen-2-yl)phosphonate (17067-93-5) + diethyl naphthalen-1-ylphosphonate (25944-75-6)

Guidance literature:

With ceric ammonium nitrate; In acetic acid; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1055/s-1987-28077

upstream raw materials:

naphthalene

phosphonic acid diethyl ester

4-chloro-2-aldehyde phenylboronic acid

(2-formyl-5-chlorophenyl)boronic acid