124755-24-4

Basic information

• Product Name: ETHYL [BIS(2,2,2-TRIFLUOROETHOXY)PHOSPHINYL]ACETATE
• Synonyms: Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate;Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate 97%;[BIS-(2,2,2-TRIFLUORO-ETHOXY)-PHOSPHORYL]-ACETIC ACID METHYL ESTER;ETHYL [BIS(2,2,2-TRIFLUOROETHOXY)PHOSPHINYL]ACETATE
• CAS NO: 124755-24-4
• Molecular Formula: C₈H₁₁F₆O₅P
• Molecular Weight: 332.13
• Product Categories: Organic Building Blocks;Phosphonates/Phosphinates;Phosphorus Compounds
• Mol File: 124755-24-4.mol

Chemical Properties

• Boiling Point: 249-250 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.403 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.3730(lit.)
• CAS DataBase Reference: ETHYL [BIS(2,2,2-TRIFLUOROETHOXY)PHOSPHINYL]ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL [BIS(2,2,2-TRIFLUOROETHOXY)PHOSPHINYL]ACETATE(124755-24-4)
• EPA Substance Registry System: ETHYL [BIS(2,2,2-TRIFLUOROETHOXY)PHOSPHINYL]ACETATE(124755-24-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 124755-24-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl [Bis(2,2,2-trifluoroethoxy)phosphinyl]acetate is used as a key intermediate in the synthesis of several bioactive compounds, including anticancer agents, calcium antagonists, and other organic compounds with potential therapeutic applications.
Used in the Preparation of Spiroketal EBC-23:
Ethyl [Bis(2,2,2-trifluoroethoxy)phosphinyl]acetate is used as a reagent for the preparation of spiroketal EBC-23, an anticancer agent. Its unique structure and reactivity contribute to the formation of the desired product, which may exhibit promising anticancer properties.
Used in the Synthesis of Scytonemin A:
This reagent is also employed in the synthesis of scytonemin A, another potential anticancer agent. Its involvement in the synthesis process highlights its versatility and importance in the development of novel pharmaceutical compounds.
Used in the Development of Novel Calcium Antagonists:
Ethyl [Bis(2,2,2-trifluoroethoxy)phosphinyl]acetate is utilized in the development of new calcium antagonists, which are essential for treating various cardiovascular conditions. Its role in the synthesis of these compounds underscores its potential impact on the healthcare industry.

Synthesis

To stirred solution of 18-crown-6 (4.40 g, 16.65 mmol), THF (20 mL), and bis (2,2,2-trifluoroethyl) phosphite (1) (0.55 mL, 3.75 mmol), KHMDS (8.0 mL, 4.00 mmol, 0.5 M in toluene) was added via syringe in a dropwise manner at -78 oC. Ethyl chloroacetate (0.35 mL, 3.30 mmol) was added to the flask after 15 min. The reaction flask was allowed to warm to room temperature and stir for 4 hr. After standard workup procedure, the crude product was then purified by flash column chromatography (2:1-1:1 hexanes:EtOAc, Rf = 0.25 in 2:1 hexanes:EtOAc) yielding Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate (808 mg, 2.43 mmol, 73.4%) as a yellow syrup.

Upstream product

• 92466-70-1 bis(2,2,2-trifluoroethyl)phosphite 
• 105-36-2 ethyl bromoacetate 
• 757-95-9 bis(2,2,2-trifluoroethyl)(methyl)phosphonate 
• 75-89-8 2,2,2-trifluoroethanol 
• 36957-54-7 ethyl 2-(dichlorophosphinyl)acetate 
• 541-41-3 chloroformic acid ethyl ester 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 

Downstream Products

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• 138283-90-6 Ethyl (E)-(4S,5R)-7-(Benzyloxy)-4,5-epoxy-4-methyl-2-heptenoate 
• 1552-92-7 ethyl cyclohexylideneacetate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 4192-77-2 ethyl cinnamate 
• 1903-22-6 ethyl cyclopentylideneacetate 
• 945-93-7 ethyl (Z)-3-phenylbut-2-enoate 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 339291-63-3 (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 
• 91348-52-6 (E)-ethyl 3-(4-nitrophenyl)-2-bromo-2-propenoate 
• 59106-34-2 (E)-ethyl 2-bromo-3-phenylpropenoate 
• 871893-64-0 (Z)/(E)-ethyl 3-(4-methoxyphenyl)-2-bromo-2-propenoate 
• 515834-87-4 (Z)-ethyl 3-(4-(allyloxy)phenyl)acrylate 

Relevant articles and documents

An expedient access to still-gennari phosphonates

An inexpensive and efficient route to the Still-Gennari phosphonates, methyl and ethyl bis(2,2,2-trifluoroethyl)phosphono acetates, has been developed. This short reaction sequence is operationally simple and makes these versatile reagents for the prepara

A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still-Gennari Type Phosphonates

Z-Selective Still-Gennari and Ando modifications of the typically E-selective Horner-Wadsworth-Emmons reaction are highly valuable synthetic tools in organic chemistry. These procedures are based on application of bis(2,2,2-trifluoroethyl) phosphonates or diaryl phosphonates, respectively, for the olefination of carbonyl groups. In our research, we present an improved, straightforward, purificationfree procedure for the synthesis of these reagents. The key step of our procedure is the reaction of phosphonic dichlorides with the appropriate sodium alkoxides, which results in 52-97% isolated yields of the desired products on a gram scale. The whole three-step process is performed in one pot. Most importantly, the product is obtained in over 95% purity after simple extraction, avoiding column chromatography and distillation. Moreover, we present the synthesis of a novel Still-Gennari type reagent, bis(1,1,1,3,3,3-hexafluoroisopropyl) phosphonates, which may exhibit improved Z-selectivity in Still-Gennari olefinations.

A convenient method for the synthesis of bis-trifluoroethyl phosphonoacetates

Bis-trifluoroethyl phosphonoacetates were easily obtained by condensation of bis-trifluoroethyl alkylphosphonates with alkyl chloroformates in the presence of 2 equivalents of lithium hexamethyldisilazane (LiHMDS).