(p-Chloro-Benzoyl)-phosphonic acid diethyl ester

Base Information

• Chemical Name: (p-Chloro-Benzoyl)-phosphonic acid diethyl ester
• CAS No.: 10570-46-4
• Molecular Formula: C11H14ClO4P
• Molecular Weight: 276.657
• DSSTox Substance ID: DTXSID20335801
• Nikkaji Number: J1.277.180K
• Wikidata: Q82102436
• Mol file: 10570-46-4.mol

Synonyms:(p-Chloro-Benzoyl)-phosphonic acid diethyl ester;10570-46-4;SCHEMBL11515099;DTXSID20335801;Diethyl 4-chlorobenzoylphosphonate;AKOS004907032

Chemical Property of (p-Chloro-Benzoyl)-phosphonic acid diethyl ester

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 276.0318236
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(=O)C1=CC=C(C=C1)Cl)OCC

Technology Process of (p-Chloro-Benzoyl)-phosphonic acid diethyl ester

There total 10 articles about (p-Chloro-Benzoyl)-phosphonic acid diethyl ester 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%

diethyl (4-chlorophenyl)(hydroxy)methylphosphonate (108054-54-2,20641-28-5) → (4-chloro-benzoyl)-phosphonic acid diethyl ester (10570-46-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.166667h; Reagent/catalyst; Solvent; Temperature; Green chemistry;

DOI:10.24820/ARK.5550190.P011.213

Reference yield: 96.9%

4-chlorophenyl thiocyanate (3226-37-7) + phosphonic acid diethyl ester (762-04-9) → (4-chloro-benzoyl)-phosphonic acid diethyl ester (10570-46-4)

Guidance literature:

With formaldehyd; palladium(II) hexafluoroacetylacetonate; 1,3-bis(pyridin-3-yl)propane-1,3-dione; In benzene; at 55 ℃; for 6h; Inert atmosphere; Darkness;

Reference yield: 95.0%

diethyl 1-amino(p-chlorophenyl)methylphosphonate (110480-88-1,110480-89-2,111408-39-0,112564-58-6) → (4-chloro-benzoyl)-phosphonic acid diethyl ester (10570-46-4)

Guidance literature:

With zinc dichromate trihydrate; at 20 ℃; for 0.0833333h; chemoselective reaction; grinding; neat (no solvent);

DOI:10.1055/s-0029-1219174

upstream raw materials:

4-chloro-benzoyl chloride

triethyl phosphite

diethyl (4-chlorophenyl)(hydroxy)methylphosphonate

4-chlorobenzaldehyde

Downstream raw materials:

diethyl 1-(p-chlorobenzoyloxy)-3,7-dimethyl-6-octenylphosphonate

diethyl (E)-cinnamylphosphonate

diethyl 1-(1'-hydroxycyclohexyl)benzylphosphonate

diethyl (2-(4-chlorophenyl)-4-oxo-3,4-dihydro-2H-pyran-2-yl)phosphonate

Refernces

• 1、 Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara. "Preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions and potassium permanganate in dry benzene". . p. 477 - 480. Retrieved 2002.
• 2、 Jaiswal, Manish K.,Singh, Ravi P.,Singh, Sanjay. "Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles". supporting information. p. 7861 - 7866. Retrieved 2021/09/28.
• 3、 Kupwade, Ravindra V.,Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.. "Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane". . p. 50 - 58. Retrieved 2021/02/26.