Diethyl (4-carbethoxybenzyl)phosphonate

Base Information

• Chemical Name: Diethyl (4-carbethoxybenzyl)phosphonate
• CAS No.: 71441-08-2
• Molecular Formula: C14H21O5P
• Molecular Weight: 300.292
• DSSTox Substance ID: DTXSID50450617
• Nikkaji Number: J517.200D
• Wikidata: Q82270407
• Mol file: 71441-08-2.mol

Synonyms:diethyl (4-carbethoxybenzyl)phosphonate;4-(diethoxy-phosphorylmethyl)benzoic acid ethyl ester;71441-08-2;diethyl 4-ethoxycarbonyl-benzylphosphonate;SCHEMBL510962;DTXSID50450617;OFUCEQWVGVURAS-UHFFFAOYSA-N;diethyl (4-carbethoxybenzyl)-phosphonate;ethyl alpha-(diethoxyphosphinyl)-p-toluate;ethyl 4-(diethoxy-phosphorylmethyl)-benzoate;4-(diethoxyphosphorylmethyl)-benzoic acid ethyl ester;4-(Ethoxycarbonyl)benzylphosphonic acid diethyl ester;4-(DIETHOXY-PHOSPHORYLMETHYL)-BENZOIC ACID ETHYL ESTER

Chemical Property of Diethyl (4-carbethoxybenzyl)phosphonate

Chemical Property:

• PSA: 71.64000
• LogP: 3.62940
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 300.11266076
• Heavy Atom Count: 20
• Complexity: 327

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC=C(C=C1)CP(=O)(OCC)OCC

Technology Process of Diethyl (4-carbethoxybenzyl)phosphonate

There total 11 articles about Diethyl (4-carbethoxybenzyl)phosphonate 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: 87.0%

Diethyl (2-oxopropyl)phosphonate (1067-71-6) + 4-iodobenzoic acid ethyl ester (51934-41-9) → ethyl 4-(diethoxyphosphorylmethyl)benzoate (71441-08-2)

Guidance literature:

With [2,2]bipyridinyl; copper(II) acetate monohydrate; potassium carbonate; In dimethyl sulfoxide; at 110 ℃; for 28h; Inert atmosphere;

DOI:10.1002/adsc.201100605

Reference yield: 76.0%

Ethyl 4-(bromomethyl)benzoate (26496-94-6) + triethyl phosphite (122-52-1) → ethyl bromide (74-96-4) + ethyl 4-(diethoxyphosphorylmethyl)benzoate (71441-08-2)

Guidance literature:

In dichloromethane; at 90 - 140 ℃; for 2h;

Reference yield: 74.0%

C5H12IO3PZn (1137728-03-0) + 4-iodobenzoic acid ethyl ester (51934-41-9) → ethyl 4-(diethoxyphosphorylmethyl)benzoate (71441-08-2)

Guidance literature:

C₅H₁₂IO₃PZn; With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,1'-bis(diphenylphosphino)ferrocene; In tetrahydrofuran; for 0.0833333h; Inert atmosphere;

4-iodobenzoic acid ethyl ester; In tetrahydrofuran; at 60 ℃; for 10h; Inert atmosphere;

DOI:10.1021/jo900142b

upstream raw materials:

ethanol

4-[(diethoxyphosphinyl)methyl]benzoic acid

Diethyl phosphonate

Ethyl 4-(bromomethyl)benzoate

Downstream raw materials:

p-<(E)-2-(1,1,3,3-tetramethyl-5-indanyl)-propenyl>-benzoic acid ethylester

(Z)-Ethyl 4-(2,6-dimethyl-1,5-heptadienyl)benzoat

(E)-Ethyl 4-(2,6-dimethyl-1,5-heptadienyl)benzoate

(Z)-Ethyl 4-(6-methoxy-2,6-dimethyl-1-heptenyl)benzoate