Diethyl (3-methylphenyl)phosphonate

Base Information

• Chemical Name: Diethyl (3-methylphenyl)phosphonate
• CAS No.: 15286-13-2
• Molecular Formula: C11H17 O3 P
• Molecular Weight: 228.228
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID50452196
• Nikkaji Number: J1.145.284A
• Wikidata: Q82272653
• Mol file: 15286-13-2.mol

Synonyms:15286-13-2;Diethyl m-tolylphosphonate;M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER;diethyl (3-methylphenyl)phosphonate;1-diethoxyphosphoryl-3-methylbenzene;MFCD00458451;1-diethoxyphosphoryl-3-methyl-benzene;SCHEMBL15871416;DTXSID50452196;PTTQZSAKTKNWSW-UHFFFAOYSA-N;AKOS017343911;M-TOLYL-PHOSPHONICACIDDIETHYLESTER;DIETHYL 3-METHYLPHENYL PHOSPHONATE;SY311556;3-Methylphenylphosphonic acid diethyl ester;3-Methylbenzenephosphonic acid, diethyl ester

Chemical Property of Diethyl (3-methylphenyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.00131mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 307.5°C at 760 mmHg
• Flash Point: 153.6°C
• PSA: 45.34000
• Density: 1.08g/cm³
• LogP: 2.88640
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 228.09153140
• Heavy Atom Count: 15
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl (3-methylphenyl)phosphonate

There total 23 articles about Diethyl (3-methylphenyl)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: 94.0%

meta-bromotoluene (591-17-3) + phosphonic acid diethyl ester (762-04-9) → diethyl (m-tolyl)phosphonate (15286-13-2)

Guidance literature:

With phthalimide; nickel(II) bromide trihydrate; tetraethylammonium hexafluorophosphate; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl acetamide; at 20 ℃; for 3h; Electrochemical reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02475

Reference yield: 94.0%

3-methylphenyltriethoxysilane (18412-56-1) + phosphonic acid diethyl ester (762-04-9) → diethyl (m-tolyl)phosphonate (15286-13-2)

Guidance literature:

3-methylphenyltriethoxysilane; With bis-triphenylphosphine-palladium(II) chloride; potassium fluoride; silver carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Sealed tube;

phosphonic acid diethyl ester; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Sealed tube;

DOI:10.1039/C6CC08408G

Reference yield: 94.0%

meta-bromotoluene (591-17-3) + triethyl phosphite (122-52-1) → diethyl (m-tolyl)phosphonate (15286-13-2)

Guidance literature:

With nickel dichloride; at 180 ℃; for 0.5h;

upstream raw materials:

3-Iodotoluene

triethyl phosphite

diethyl trimethylsilyl phosphate

meta-bromotoluene

Downstream raw materials:

(E)-ethyl 3-(2-(diethoxyphosphoryl)-4-methylphenyl)acrylate

C₁₂H₁₆NO₃P

(E)-diethyl (2-(1,2-diphenylvinyl)-5-methylphenyl)phosphonate

(Z)-diethyl (2-(1,2-diphenylvinyl)-5-methylphenyl)phosphonate

Refernces

• 1、 Doherty, Simon,Knight, Julian G.,Tran, Tina S. T.,Alharbi, Hussam Y.,Perry, Daniel O.. "The Synthesis of Biarylmonophosphonates via Palladium-Catalyzed Phosphonation, Iridium-Catalyzed C-H Borylation, Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling". . p. 398 - 413. Retrieved 2021/05/13.
• 2、 Hosseini-Sarvari, Mona,Koohgard, Mehdi. "Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine". . p. 5905 - 5911. Retrieved 2021/07/12.