Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate

Base Information

• Chemical Name: Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate
• CAS No.: 124755-24-4
• Molecular Formula: C8H11 F6 O5 P
• Molecular Weight: 332.137
• European Community (EC) Number: 628-627-0
• DSSTox Substance ID: DTXSID80471931
• Nikkaji Number: J452.521C
• Wikidata: Q82300632
• Mol file: 124755-24-4.mol

Synonyms:124755-24-4;Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate;Ethyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate;Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate;Ethyl[bis(2,2,2-trifluoroethoxy)phosphinyl]acetate;MFCD01318337;Acetic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, ethyl ester;Ethyl [bis(2,2,2-trifluoroethoxy)phosphoryl]acetate;C8H11F6O5P;SCHEMBL1135973;DTXSID80471931;Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, ethyl ester;AKOS015913541;CS-W004772;AS-72186;SY112987;A890362;ethyl[bis(2,2,2-trifluoro-ethoxy)phosphinyl]acetate;bis(2,2,2-trifluoroethyl)(ethoxycarbonylmethyl)-phosphonate;Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate, >=96%;[Bis-(2,2,2 trifluoro-ethoxy)-phosphoryl]-acetic acid ethyl ester

Chemical Property of Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate

Chemical Property:

• Refractive Index: n20/D 1.3730(lit.)
• Boiling Point: 249-250 °C(lit.)
• Flash Point: >230 °F
• PSA: 71.64000
• Density: 1.403 g/mL at 25 °C(lit.)
• LogP: 2.90040
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 332.02482942
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl[Bis(2,2,2-trifluoroethoxy)phosphinyl]acetate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CP(=O)(OCC(F)(F)F)OCC(F)(F)F
• Uses: Ethyl [Bis(2,2,2-trifluoroethoxy)phosphinyl]acetate is a reagent used in the preparation of spiroketal EBC-23; an anticancer agent, scytonemin A; a novel calcium antagonist and other useful organic compounds.

Technology Process of Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate

There total 6 articles about Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate 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: 79.0%

chloroformic acid ethyl ester (541-41-3) + bis(2,2,2-trifluoroethyl)(methyl)phosphonate (757-95-9) → ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate (124755-24-4)

Guidance literature:

chloroformic acid ethyl ester; bis(2,2,2-trifluoroethyl)(methyl)phosphonate; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 - -20 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; hexane; dichloromethane; at -20 ℃; Inert atmosphere;

DOI:10.15227/orgsyn.073.0152

Reference yield: 52.0%

ethyl 2-(dichlorophosphinyl)acetate (36957-54-7) + sodium 2,2,2-trifluoroethanolate (420-87-1) → ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate (124755-24-4)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1055/a-1628-7586

Reference yield: 30.0%

bis(2,2,2-trifluoroethyl)phosphite (92466-70-1) + ethyl bromoacetate (105-36-2) → ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate (124755-24-4)

Guidance literature:

bis(2,2,2-trifluoroethyl)phosphite; With sodium hydride; In tetrahydrofuran; at -42 ℃;

ethyl bromoacetate; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1080/00304949909355724

upstream raw materials:

bis(2,2,2-trifluoroethyl)phosphite

ethyl bromoacetate

bis(2,2,2-trifluoroethyl)(methyl)phosphonate

2,2,2-trifluoroethanol

Downstream raw materials:

(Z)/(E)-ethyl 3-(4-methoxyphenyl)-2-bromo-2-propenoate

(E)-ethyl 2-bromo-3-phenylpropenoate

(E)-ethyl 3-(4-nitrophenyl)-2-bromo-2-propenoate

(Z)-4-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-2-methyl-but-2-enoic acid ethyl ester

Refernces

• 1、 Janicki, Ignacy,Kie?basiński, Piotr. "A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still-Gennari Type Phosphonates". . p. 378 - 382. Retrieved 2021/10/21.
• 2、 Patois, Carl,Savignac, Philippe,About-Jaudet, Elie,Collignon, No?l,Daniewski, Andrzej R.,Tilley, Bryon K.,Coffen, David L.. "Bis(trifluoroethyl) (carboethoxymethyl) phosphonate: [Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, ethyl ester]". . p. 152 - 152. Retrieved 2017/09/08.