Triethyl 2-phosphonopropionate

Base Information

• Chemical Name: Triethyl 2-phosphonopropionate
• CAS No.: 3699-66-9
• Molecular Formula: C9H19O5P
• Molecular Weight: 238.221
• Hs Code.: 29319019
• European Community (EC) Number: 223-033-4
• NSC Number: 202767
• DSSTox Substance ID: DTXSID50958163
• Nikkaji Number: J205.616J
• Mol file: 3699-66-9.mol

Synonyms:Triethyl 2-phosphonopropionate;3699-66-9;Ethyl 2-(diethoxyphosphoryl)propanoate;ethyl 2-diethoxyphosphorylpropanoate;Ethyl-2-(diethylphosphono)propanoate;MFCD00009159;C9H19O5P;Propanoic acid, 2-(diethoxyphosphinyl)-, ethyl ester;EINECS 223-033-4;Diethyl 1-(carbethoxy)ethylphosphonate;Diethyl 1-(Ethoxycarbonyl)Ethanephosphonate~2-Phosphonopropionic Acid Triethyl Ester;2-(diethoxyphosphoryl)propionic acid ethyl ester;NSC202767;SCHEMBL10108;triethyl 2-phosponopropionate;DIETHYL 1-(ETHOXYCARBONYL)ETHANEPHOSPHONATE;TRIethyl 2-PHOSPHONOpropanoate;DTXSID50958163;ethyl 2-diethylphosphonopropionate;BCP28350;C9-H19-O5-P;Ethyl 2-(diethylphosphono)propanoate;ethyl 2-(diethylphosphono)propionate;Ethyl2-(diethoxyphosphoryl)propanoate;Triethyl 2-phosphonopropionate, 98%;Ethyl 2 -(diethylphosphono)propanoate;ethyl 2-(diethyl phosphono)propanoate;AKOS016001420;Ethyl 2~(diethoxyphosphoryl)propanoate;ethyl-2-(diethoxyphosphinyl)propionate;CS-W014152;NSC-202767;2-Phosphonopropanoic acid triethyl ester;2-Phosphonopropionic Acid Triethyl Ester;diethyl 1-ethoxycarbonyl-ethylphosphonate;AS-19804;SY010659;ethyl 2-(diethoxyphosphoryl)-2-methylacetate;FT-0634979;T2135;EN300-98229;2-(Diethoxy-phosphoryl)-propionic acid ethyl ester;A823496;J-525071

Chemical Property of Triethyl 2-phosphonopropionate

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 0.00507mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 275.5 °C at 760 mmHg
• Flash Point: 88.9 °C
• PSA: 71.64000
• Density: 1.093 g/cm³
• LogP: 2.20410
• Storage Temp.: -20°C
• Solubility.: Miscible with chloroform and methanol.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 238.09701070
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

97% ^*data from raw suppliers

Triethyl 2-phosphonopropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 23-24/25-36-26-39-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(C)P(=O)(OCC)OCC
• Uses: Triethyl 2-Phosphonopropionate is used in studies involving insecticides and their efficacy on various bacterium. Also act as inhibitors of Epstein-Bar virus transmission and infections. Triethyl 2-phosphonopropionate is used as a reactant in intramolecular conjugate addition for the synthesis of floresolide B, enantioselective synthesis of spiroindane di-methyl acetic acid and in stereo selective intramolecular Diels-Alder reactions. It plays an important role in Horner-Wadsworth-Emmons reactions and chemoenzymatic one-pot synthesis of gamma-butyrolactones. It is also used in the preparation of 3-[2]furyl-2-methyl-acrylic acid ethyl ester by reacting with furfural.

Technology Process of Triethyl 2-phosphonopropionate

There total 28 articles about Triethyl 2-phosphonopropionate 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%

Ethyl 2-bromopropionate (535-11-5,41978-69-2) + triethyl phosphite (122-52-1) → ethyl 2-diethoxyphosphorylpropionate (3699-66-9)

Guidance literature:

for 36h; Reflux;

DOI:10.1039/c6ob00938g

Reference yield: 76.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + methyl iodide (74-88-4) → ethyl 2-diethoxyphosphorylpropionate (3699-66-9)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01067

Reference yield: 76.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl 2-diethoxyphosphorylpropionate (3699-66-9)

Guidance literature:

With sodium hydride; In diethyl ether; for 3h;

upstream raw materials:

sodium diethyl phosphite

Ethyl 2-bromopropionate

triethyl phosphite

diethoxyphosphoryl-acetic acid ethyl ester

Downstream raw materials:

2-Phosphono-propionsaeure

2-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propionic acid ethyl ester

ethyl 5-(4'-isopropylphenyl)-2-methyl-trans-2-pentenoate

ethyl 5-(4'-isopropylphenyl)-2-methyl-cis-2-pentenoate

Refernces

• 1、 Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng. "Copper-Catalyzed Dehydrogenative Diels-Alder Reaction". supporting information. p. 3215 - 3219. Retrieved 2018/06/11.
• 2、 Coxon, Fraser,Joachimiak, ?ukasz,Najumudeen, Arafath Kaja,Breen, George,Gmach, Joanna,Oetken-Lindholm, Christina,Way, Rebecca,Dunford, James,Abankwa, Daniel,B?azewska, Katarzyna M.. "Synthesis and characterization of novel phosphonocarboxylate inhibitors of RGGT". supporting information. p. 77 - 89. Retrieved 2014/07/22.