Diethyl 4-(benzyloxy)benzylphosphonate

Base Information

• Chemical Name: Diethyl 4-(benzyloxy)benzylphosphonate
• CAS No.: 131719-55-6
• Molecular Formula: C₁₈H₂₃O₄P
• Molecular Weight: 334.352
• DSSTox Substance ID: DTXSID20435476
• Nikkaji Number: J517.217I
• Mol file: 131719-55-6.mol

Synonyms:Diethyl 4-(benzyloxy)benzylphosphonate;131719-55-6;Diethyl4-(benzyloxy)benzylphosphonate;SCHEMBL8011004;DTXSID20435476;F80745;4-(Benzyloxy)benzylphosphonic acid diethyl ester;1-(diethoxyphosphorylmethyl)-4-phenylmethoxybenzene

Chemical Property of Diethyl 4-(benzyloxy)benzylphosphonate

Chemical Property:

• Boiling Point: 466.0±33.0 °C(Predicted)
• Density: 1.139±0.06 g/cm3(Predicted)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 334.13339621
• Heavy Atom Count: 23
• Complexity: 350

Purity/Quality:

≥99% ^*data from raw suppliers

Diethyl4-(benzyloxy)benzylphosphonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC1=CC=C(C=C1)OCC2=CC=CC=C2)OCC

Technology Process of Diethyl 4-(benzyloxy)benzylphosphonate

There total 4 articles about Diethyl 4-(benzyloxy)benzylphosphonate 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: 98.0%

4-(benzyloxy)benzyl bromide (5544-60-5) + triethyl phosphite (122-52-1) → diethyl <4-(benzyloxy)benzyl>phosphonate (131719-55-6)

Guidance literature:

at 160 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jm1006929

Reference yield: 92.0%

4-benzyloxybenzyl chloride (836-42-0) + triethyl phosphite (122-52-1) → diethyl <4-(benzyloxy)benzyl>phosphonate (131719-55-6)

Guidance literature:

at 160 ℃; Inert atmosphere;

DOI:10.1039/c4nj00654b

Reference yield:

4-benzyloxybenzyl alcohol (836-43-1) → diethyl <4-(benzyloxy)benzyl>phosphonate (131719-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / PBr₃ / CH₂Cl₂ / 3 h / 0 - 23 °C

2: 94 percent / tetrabutylammonium iodide / 10 h / 110 - 130 °C

With phosphorus tribromide; tetra-(n-butyl)ammonium iodide; In dichloromethane;

DOI:10.1021/jm00072a015

upstream raw materials:

4-(benzyloxy)benzyl bromide

triethyl phosphite

4-benzyloxybenzyl chloride

p-benzyloxybenzaldehyde

Downstream raw materials:

trans-4,4'-dihydroxystilbene

diethyl 4-(hydroxy)benzylphosphonate

bibenzyl-2,4'-diol

(E)-4-<2-(3-hydroxyphenyl)ethenyl>phenol

Refernces

• 1、 Flaherty, Daniel P.,Kiyota, Tomomi,Dong, Yuxiang,Ikezu, Tsuneya,Vennerstrom, Jonathan L.. "Phenolic bis-styrylbenzenes as β-amyloid binding ligands and free radical scavengers". supporting information; experimental part. p. 7992 - 7999. Retrieved 2011/03/19.
• 2、 Boyer, Serge H.,Jiang, Hongjian,Jacintho, Jason D.,Reddy, Mali Venkat,Li, Haiqing,Li, Wenyu,Godwin, Jennifer L.,Schulz, William G.,Cable, Edward E.,Hou, Jinzhao,Wu, Rongrong,Fujitaki, James M.,Hecker, Scott J.,Erion, Mark D.. "Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs". experimental part. p. 7075 - 7093. Retrieved 2009/11/30.