Triethyl 2-fluoro-2-phosphonoacetate

Base Information

• Chemical Name: Triethyl 2-fluoro-2-phosphonoacetate
• CAS No.: 2356-16-3
• Molecular Formula: C8H16FO5P
• Molecular Weight: 242.184
• Hs Code.: 29319090
• European Community (EC) Number: 627-648-2
• DSSTox Substance ID: DTXSID20946330
• Nikkaji Number: J247.275I
• Mol file: 2356-16-3.mol

Synonyms:Triethyl 2-fluoro-2-phosphonoacetate;2356-16-3;2-Fluoro-2-phosphonoacetic Acid Triethyl Ester;ethyl 2-diethoxyphosphoryl-2-fluoroacetate;ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate;ethyl (diethoxyphosphoryl)(fluoro)acetate;Triethyl fluorophosphonoacetate;Triethyl phosphonofluoroacetate;Acetic acid, (diethoxyphosphinyl)fluoro-, ethyl ester;ethyl diethylphosphonofluoroacetate;triethyl-2-fluoro-2-phosphonoacetate;MFCD00134400;C8H16FO5P;diethyl [(ethoxycarbonyl)fluoromethyl]phosphonate;Triethyl2-fluoro-2-phosphonoacetate;(Diethoxyphosphinyl)fluoroacetic Acid Ethyl Ester;SCHEMBL365852;FVPISMANESAJQZ-UHFFFAOYSA-;DTXSID20946330;FVPISMANESAJQZ-UHFFFAOYSA-N;C8-H16-F-O5-P;triethyl-2-fluoro-2-phophonoacetate;ethyl diethyl-phosphono-fluoroacetate;BBL101901;STL555698;ethyl 2-fluoro-diethylphosphonoacetate;ethyl diethyl-phosphono-fluoro-acetate;ethyl diethylphosphono-2-fluoroacetate;AKOS005762918;Ethyl (Diethoxyphosphinyl)fluoroacetate;Triethyl 2-fluoro -2-phosphonoacetate;AM61425;CS-W012781;ethyl 2-fluoro-2-diethylphosphonoacetate;AS-18223;SY017649;Triethyl 2-fluoro-2-phosphonoacetate, 96%;ethyl 2-(diethyl phosphono)-2-fluoroacetate;F0340;FT-0634212;Diethoxyphosphinylfluoroacetic acid ethyl ester;EN300-98009;(Diethoxyphosphinyl)fluoroacetic acid, ethyl ester;A816768;(diethoxy-phosphoryl)-fluoro-acetic acid ethyl ester;J-509355;Acetic acid, 2-(diethoxyphosphinyl)-2-fluoro-, ethyl ester;InChI=1/C8H16FO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3

Chemical Property of Triethyl 2-fluoro-2-phosphonoacetate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 9.13E-05mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 339.5 °C at 760 mmHg
• Flash Point: 73.9 °C
• PSA: 71.64000
• Density: 1.171 g/cm³
• LogP: 2.11120
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 242.07193877
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

99% ^*data from raw suppliers

Triethyl 2-fluoro-2-phosphonoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; F
• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(F)P(=O)(OCC)OCC
• Uses: Reactant for: Diels-Alder reactionsBiosynthesis of terpeneStereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonatesSynthesis of quinolonesHorner-Wadsworth-Emmons asymmetric hydrationAddition reactions and the subsequent application to click chemistryAsymmetric intermolecular Stetter reactions

Technology Process of Triethyl 2-fluoro-2-phosphonoacetate

There total 15 articles about Triethyl 2-fluoro-2-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: 96.4%

ethyl bromofluoroacetate (401-55-8) + triethyl phosphate (78-40-0) → ethyl(diethylphosphono)(fluoro)acetate (2356-16-3)

Guidance literature:

With 15-crown-5; In o-xylene; at 105 ℃; for 14h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 94.0%

ethyl bromofluoroacetate (401-55-8) + triethyl phosphite (122-52-1) → ethyl(diethylphosphono)(fluoro)acetate (2356-16-3)

Guidance literature:

for 0.0333333h; microwave irradiation;

DOI:10.1080/10426500008043680

Reference yield: 78.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl(diethylphosphono)(fluoro)acetate (2356-16-3)

Guidance literature:

With sodium hexamethyldisilazane; N-Fluoro-o-benzenedisulfonimide; In tetrahydrofuran; 1.) -78 deg C, 10 min; -78 to 0 deg C, 0.5 h, 2.) 0 deg C, 2 h;

DOI:10.1021/jo00120a014

upstream raw materials:

ethyl chlorofluoroacetate

phosphonic acid diethyl ester

Potassium; (Z)-2-(diethoxy-phosphoryl)-1,2-bis-ethoxycarbonyl-ethenolate

ethyl bromofluoroacetate

Downstream raw materials:

ethyl (E)-2-fluoro-3-phenylacrylate

ethyl 2,4-difluoro-5-phenyl-2(E),4(E)-pentadienoate

(2E,4Z,6Z)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid ethyl ester

(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-5-phenyl-7-(tetrahydro-pyran-2-yloxy)-hept-2-enoic acid ethyl ester

Refernces

• 1、 Tsai, Hou-Jen. "Application of fluorocarbethoxy-substituted phosphonate: A facile entry to substituted 2-fluoro-3-oxoesters". . p. 1 - 10. Retrieved 1997.
• 2、 Waschbuesch, Rachel,Carran, John,Savignac, Philippe. "New routes to diethyl 1-fluoromethylphosphonocarboxylates and diethyl 1-fluoromethylphosphonocarboxylic acid". . p. 6391 - 6400. Retrieved 1997.
• 3、 -. "Triethyl 2-fluoro-2-phosphonoacetate synthesis method". Paragraph 0017-0021. . Retrieved 2019/08/01.
• 4、 -. "INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE". Page/Page column 162. . Retrieved 2017/09/02.