Diethyl hydroxy(phenyl)methylphosphonate

Base Information

• Chemical Name: Diethyl hydroxy(phenyl)methylphosphonate
• CAS No.: 1663-55-4
• Molecular Formula: C11H17 O4 P
• Molecular Weight: 244.227
• Hs Code.: 2931900090
• NSC Number: 43154
• DSSTox Substance ID: DTXSID60285891,DTXSID80942232
• Nikkaji Number: J462.904C
• ChEMBL ID: CHEMBL1413420
• Mol file: 1663-55-4.mol

Synonyms:1663-55-4;diethyl [hydroxy(phenyl)methyl]phosphonate;Diethyl hydroxy(phenyl)methylphosphonate;diethoxyphosphoryl(phenyl)methanol;Phosphonic acid, P-(hydroxyphenylmethyl)-, diethyl ester;diethyl[hydroxy(phenyl)methyl]phosphonate;MLS001044389;SCHEMBL6756690;CHEMBL1413420;DTXSID60285891;DTXSID80942232;HMS2789A09;BAA66355;NSC43154;NSC-43154;STK830793;AKOS005068051;20176-43-6;Diethyl hydroxy(phenyl)methylphosphonate #;SMR000424920;alpha-hydroxybenzylphosphonic acid diethyl ester;EN300-235770;alpha-hydroxybenzyl-phosphonic acid diethyl ester;(alpha-Hydroxybenzyl)phosphonic acid, diethyl ester;(Hydroxy-phenyl-methyl)-phosphonic acid diethyl ester;Phosphonic acid, (hydroxyphenylmethyl)-, diethyl ester;F0794-0009

Chemical Property of Diethyl hydroxy(phenyl)methylphosphonate

Chemical Property:

• Vapor Pressure: 7.1E-06mmHg at 25°C
• Melting Point: 83 °C
• Refractive Index: 1.507
• Boiling Point: 362°Cat760mmHg
• PKA: 12.19±0.20(Predicted)
• Flash Point: 172.8°C
• PSA: 65.57000
• Density: 1.18g/cm³
• LogP: 2.94360
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 244.08644602
• Heavy Atom Count: 16
• Complexity: 228

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(C1=CC=CC=C1)O)OCC
• Uses: Diethyl [Hydroxy(phenyl)methyl]phosphonate is a useful intermediate in the chitosan catalyzed synthesis of diethyl hydroxy (substituted phenyl) methylphosphonates with antioxidant activities.

Technology Process of Diethyl hydroxy(phenyl)methylphosphonate

There total 33 articles about Diethyl hydroxy(phenyl)methylphosphonate 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: 100.0%

benzaldehyde (100-52-7) + phosphonic acid diethyl ester (762-04-9) → diethyl [hydroxy(phenyl)methyl]phosphonate (1663-55-4)

Guidance literature:

DOI:10.1007/s11176-005-0386-8

Reference yield: 99.0%

benzaldehyde (100-52-7) + triethyl phosphite (122-52-1) → diethyl [hydroxy(phenyl)methyl]phosphonate (1663-55-4)

Guidance literature:

With cerium(IV) oxide; diethylamine; for 0.333333h; Sonication; Neat (no solvent);

DOI:10.1016/j.tetlet.2011.04.112

Reference yield: 96.0%

Diethyl phosphonate (762-04-9,123-22-8) + benzaldehyde (100-52-7) → diethyl [hydroxy(phenyl)methyl]phosphonate (1663-55-4)

Guidance literature:

Diethyl phosphonate; With [(Me₃Si)₂N]₃La(μ-Cl)Li(THF)₃; In toluene; for 0.166667h; Inert atmosphere;

benzaldehyde; In toluene; at 25 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1021/jo101743e

upstream raw materials:

benzaldehyde

phosphonic acid diethyl ester

diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate

Acetic acid (diethoxy-phosphoryl)-methylsulfanyl-methyl ester

Downstream raw materials:

(diethoxyphosphoryl)(phenyl)methyl acetate

N,N,N',N'-Tetraaethyl-P-(α-hydroxybenzyl)-phosphonyl-diamid

O-Aethyl-N,N-diaethyl-P-<α-hydroxy-benzyl>-phosphonoamidat

α-chlorobenzylphosphonic acid diethyl ester

Refernces

• 1、 Nakanishi, Kyoko,Kotani, Shunsuke,Sugiura, Masaharu,Nakajima, Makoto. "First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases". . p. 6415 - 6419. Retrieved 2008.
• 2、 Matveeva,Zefirov. "On the mechanism of the Kabachnik-Fields reaction: Does a mechanism of nucleophilic amination of α-hydroxyphosphonates exist?". . p. 137 - 140. Retrieved 2008.
• 3、 Ouksel, Louiza,Chafaa, Salah,Bourzami, Riadh,Hamdouni, Noudjoud,Sebais, Miloud,Chafai, Nadjib. "Crystal structure, vibrational, spectral investigation, quantum chemical DFT calculations and thermal behavior of Diethyl [hydroxy (phenyl) methyl] phosphonate". . p. 389 - 395. Retrieved 2017.
• 4、 Tsai, Hou-Jen,Hsieh, Chi-Wei. "Tetrafluorine-containing ketones and acetoacetates: Synthesis and mechanistic study". . p. 749 - 757. Retrieved 2007.
• 5、 Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi. "An efficient and simple strategy toward the synthesis of highly functionalized compounds". . p. 978 - 995. Retrieved 2021/08/06.
• 6、 -. "Method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis". Paragraph 0024-0026. . Retrieved 2020/05/01.