Triethyl phosphonoacetate

Base Information

• Chemical Name: Triethyl phosphonoacetate
• CAS No.: 867-13-0
• Deprecated CAS: 874204-68-9
• Molecular Formula: C8H17O5P
• Molecular Weight: 224.194
• Hs Code.: 29310095
• European Community (EC) Number: 212-757-6
• NSC Number: 16128,13898
• UNII: 022826171T
• DSSTox Substance ID: DTXSID4041573
• Nikkaji Number: J54.207E
• Wikipedia: Triethyl_phosphonoacetate
• Wikidata: Q7841458
• ChEMBL ID: CHEMBL3185304
• Mol file: 867-13-0.mol

Synonyms:NSC-13898;NSC-16128;triethyl phosphonoacetate

Chemical Property of Triethyl phosphonoacetate

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: -24 °C
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 287.4 °C at 760 mmHg
• Flash Point: 141.6 °C
• PSA: 71.64000
• Density: 1.13 g/cm³
• LogP: 1.81560
• Storage Temp.: Refrigerator
• Water Solubility.: Slightly miscible with water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 224.08136064
• Heavy Atom Count: 14
• Complexity: 206

Purity/Quality:

99% ^*data from raw suppliers

Triethyl phosphonoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,Xi,Xn
• Hazard Codes: N,Xi,Xn
• Statements: 51/53-36/37/38
• Safety Statements: 61-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: CCOC(=O)CP(=O)(OCC)OCC
• Uses: Triethyl phosphonoacetate is used for Horner-Emmons modification. Triethyl phosphonoacetate serves as a reactant used in Horner-Wadsworth-Emmons reactions, Tsuji-Trost type reactions, Intramolecular Heck-type cyclization and isomerizations and Intramolecular aryne-ene reactions. In Horner-Wadsworth-Emmons reaction, it is utilized as a reagent to prepare chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.

Technology Process of Triethyl phosphonoacetate

There total 38 articles about Triethyl phosphonoacetate 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%

ethyl bromoacetate (105-36-2) + triethyl phosphite (122-52-1) → diethoxyphosphoryl-acetic acid ethyl ester (867-13-0)

Guidance literature:

at 60 - 80 ℃; for 0.5h;

DOI:10.1002/1099-0690(200209)2002:17<3015::AID-EJOC3015>3.0.CO;2-G

Reference yield: 95.0%

chloroacetic acid ethyl ester (105-39-5) + triethyl phosphite (122-52-1) → diethoxyphosphoryl-acetic acid ethyl ester (867-13-0)

Guidance literature:

In toluene; at 170 ℃; for 0.333333h; under 7500.75 Torr; Pressure; Temperature; Large scale;

Reference yield: 89.3%

chloroacetic acid ethyl ester (105-39-5) → diethoxyphosphoryl-acetic acid ethyl ester (867-13-0)

Guidance literature:

With triethyl phosphite;

upstream raw materials:

diethyl ether

sodium diethyl phosphite

chloroacetic acid ethyl ester

benzene

Downstream raw materials:

ethyl 2-diethoxyphosphinoylacrylate

monoethylphosphonoacetic acid

diethyl carbamoylmethylphosphonate

ethyl 2-(diethoxyphosphoryl)hexanoate

Refernces

Selenylated dienes: synthesis, stereochemical studies by ⁷⁷Se NMR, and transformation into functionalized allenes

10.1016/j.tet.2007.02.082

The study focuses on the synthesis, stereochemical analysis, and functional transformations of 2-phenylselanyl-1,3-dienes. The researchers prepared these dienes using Wittig or Wittig-Horner-Emmons reactions, starting from α-phenylselanyl α,β-unsaturated aldehydes. They determined the ratio and configuration of the diene isomers using 77Se and 1H NMR spectroscopy. The dienes were then oxidized to selenoxides, which underwent [2,3]-sigmatropic rearrangements in THF, leading to the formation of allenyl alcohols, allenyl carbamates, and 1-haloalkyl allenes. This work explores the potential of selenoxides, selenimides, and dihalo-selenuranes in organic synthesis, providing a mild and selective method for preparing various functionalized allenes. The study also discusses the implications of these findings in the context of organic synthesis, including the potential use of these compounds in Diels-Alder cycloaddition reactions and as precursors for other synthetic transformations.

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