4-[(Diethoxyphosphoryl)methyl]benzoic acid

Base Information

• Chemical Name: 4-[(Diethoxyphosphoryl)methyl]benzoic acid
• CAS No.: 28149-48-6
• Molecular Formula: C12H17O5P
• Molecular Weight: 272.238
• DSSTox Substance ID: DTXSID50548280
• Nikkaji Number: J517.198I
• Wikidata: Q82426931
• Mol file: 28149-48-6.mol

Synonyms:28149-48-6;4-[(diethoxyphosphoryl)methyl]benzoic acid;4-(Diethoxyphosphinylmethyl)benzoic acid;4-(diethoxyphosphorylmethyl)benzoic acid;4-((DIETHOXYPHOSPHORYL)METHYL)BENZOIC ACID;4-Carboxyphenyl Phosphonate;SCHEMBL454324;diethyl 4-carboxybenzylphosphonate;DTXSID50548280;BYKRBDLOUKSWNM-UHFFFAOYSA-N;4-diethoxyphosphinylmethylbenzoic acid;AKOS005067805;4-(Diethoxyphosphinylmethyl)benzoicacid;AM803632;4-[(diethoxyphosphinyl)methyl]benzoic acid;4-[(Diethoxyphosphinoyl)methyl]benzoic acid;VU0549298-1;EN300-235863;4-(diethoxyphosphorylmethyl)benzenecarboxylic acid;A848209;A1-33281;J-016988;F9995-0119

Chemical Property of 4-[(Diethoxyphosphoryl)methyl]benzoic acid

Chemical Property:

• PSA: 82.64000
• LogP: 3.15090
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 272.08136064
• Heavy Atom Count: 18
• Complexity: 300

Purity/Quality:

97% ^*data from raw suppliers

4-(Diethoxyphosphinylmethyl)benzoicAcid ^*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)C(=O)O)OCC
• Uses: Used for the preparation of cholesterol acyltransferase-1 (ACAT-1) inhibitors suitable for use as antiarteriosclerotic and anticholesteremic agents.

Technology Process of 4-[(Diethoxyphosphoryl)methyl]benzoic acid

There total 6 articles about 4-[(Diethoxyphosphoryl)methyl]benzoic acid 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: 99.0%

p-(chloromethyl)benzoic acid (1642-81-5) + phosphonic acid diethyl ester (762-04-9) → 4-[(diethoxyphosphinyl)methyl]benzoic acid (28149-48-6)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; for 4h; Reflux; Inert atmosphere;

DOI:10.1039/b9nj00585d

Reference yield: 98.0%

4-bromomethylbenzoic Acid (6232-88-8) + triethyl phosphite (122-52-1) → 4-[(diethoxyphosphinyl)methyl]benzoic acid (28149-48-6)

Guidance literature:

for 20h; Heating / reflux;

Reference yield: 82.0%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + triethyl phosphite (122-52-1) → 4-[(diethoxyphosphinyl)methyl]benzoic acid (28149-48-6)

Guidance literature:

Methyl 4-(bromomethyl)benzoate; triethyl phosphite; at 130 ℃; for 4h;

With lithium hydroxide; In methanol; at 20 ℃; for 4h; Further stages.;

DOI:10.1021/ja802407f

upstream raw materials:

4-bromomethylbenzoic Acid

triethyl phosphite

Methyl 4-(bromomethyl)benzoate

p-(chloromethyl)benzoic acid

Downstream raw materials:

ethyl 4-(diethoxyphosphorylmethyl)benzoate

(4-carboxyphenyl)methylphosphonic acid

4-[(diethoxyphosphoryl)-methyl]benzoyl chloride

diethyl (4-(hydroxymethyl)benzyl)phosphonate