2397-47-9

Usage

Uses

Used in Organic Synthesis:
Triethyl phenylphosphorimidate serves as a valuable reagent in organic synthesis, utilized for the production of phosphor-imidate derivatives of nucleic acids and other biologically active molecules. Its unique structure allows for the formation of these derivatives, which are essential in various applications across different scientific fields.
Used in Solid-Phase Synthesis of Oligonucleotides:
In the field of molecular biology, triethyl phenylphosphorimidate is employed as a phosphitylating agent in the solid-phase synthesis of oligonucleotides. It facilitates the formation of phosphodiester linkages between nucleotide units, which is crucial for the construction of these genetic sequences.
Used in the Synthesis of Peptide Nucleic Acids:
Triethyl phenylphosphorimidate also plays a significant role in the synthesis of peptide nucleic acids (PNAs). It functions as a coupling reagent, enabling the formation of PNAs that have unique properties and potential applications in molecular biology and medicine.
Used in Biology, Medicine, and Material Science:
The applications of triethyl phenylphosphorimidate extend to the production of a broad spectrum of functional molecules and biomolecules. Its contribution to the synthesis of these molecules makes it an indispensable component in the advancement of research and development in biology, medicine, and material science.

Upstream product

• 62-53-3 aniline 
• 122-52-1 triethyl phosphite 
• 622-37-7 Phenyl azide 

Downstream Products

• 1445-38-1 diethyl phenylphosphoramidate 
• 36894-92-5 diethyl (N-acetyl-N-phenylamido)phosphate 
• 52670-78-7 O,O'-diethyl methyl(phenyl)amidophosphate 
• 25626-89-5 O,O-diethyl-N-ethyl-N-phenyl-phosphoramidate 
• 102969-03-9 C₁₈H₂₆NO₇P 
• 73755-65-4 (OC₂H₅)2P(O)N(C₂H₅)C₆H₅(BF₃) 
• 102969-19-7 (E)-2-(Diethoxy-phosphoryl)-3-phenylamino-but-2-enedioic acid dimethyl ester 
• 102969-19-7 (E)-2-(Diethoxy-phosphoryl)-3-phenylamino-but-2-enedioic acid dimethyl ester 
• 102969-20-0 2,2,2-Triethoxy-1-phenyl-1,2-dihydro-2λ⁵-[1,2]azaphosphinine-3,4,5,6-tetracarboxylic acid tetramethyl ester 
• 102969-23-3 2,2,4-Triethoxy-1-phenyl-1,4-dihydro-2λ⁵-[1,2]azaphosphinine-3,4,5,6-tetracarboxylic acid tetramethyl ester 
• 133827-74-4 C₉H₅⁽²⁾H₉NO₃P 

Relevant academic research and scientific papers

Reactivity of N phenyl iminophosphoranes towards ozone: Evidence of trioxo azaphospholane intermediates

The ozonation of N-phenyl-iminophosphoranes R3P=NPh 1a-b leads, after the P-N bond breakage, to the corresponding phosphorus oxides 2a-b with the formation of complex adducts 3a-b which precipitate at room temperature. The stoichiometry and the reaction mechanism depend on the nature of substituents R linked to the phosphorus atom. For R=Ph we detected the phosphonium intermediate 5a, whereas for R=OEt the trioxoazaphospholanes 7b-9b were characterized by 31P NMR.

Reactions de tris(alcoxy)iminophosphanes avec l'acetylene dicarboxylate de methyle: ylure, phosphonate et phosphorane

The tris(alkoxy) N-phenyl iminophosphanes react under mild conditions with acetylenic carboxylates to give phosphorus ylides with a β carbonyl group.These compounds, well characterized in the reaction mixture, have not been isolated.They are highly reactive and depending on the nature of substituents on phosphorus atom; give phosphonates, phosphoranes and cyclic ylides.

ARYLIMINO DERIVATIVES OF METHYL-1,3,2λ5-DIOXAPHOSPHOLANES. SYNTHESIS AND DIMERIZATION

The tendency of 2-alkoxy-2-(arylimino)-1,3,2λ5-dioxaphospholanes to dimerize with the formation of the corresponding diazadiphosphetidines falls substantially on the introduction of acceptor substituents on the imino nitrogen and of four methyl groups into the heterocycle, which lower the inductive acceptor power of the cyclic substituent and shield the phosphorus atom.

ON THE REACTION OF PHOSPHORUS ACID ESTERS WITH NUCLEOPHILES IN THE PRESENCE OF CARBON TETRACHLORIDE

Esters of N-Phosphoryl phosphazenes are prepared by a modified Atherton-Todd reaction from di- and triesters of phosphorous acid, sodium azide, and carbon tetrachloride in high yields.The utilization of the two-component system trialkyl phosphite/ carbon tetrachloride for preparing phosphazenes, (RO)3P=NY (Y: PO(OR)2, SO2R, COR, CN), and dialkoxyphosphoryl compounds, (RO)2P(O)X (X: NHR, NR2, OPh, CN, F, NCO), is presented.

INDUCTIVE AND STERIC EFFECTS IN THE STAUDINGER REACTION

The sterically unhindered mode of the electrophilic addition of phenyl azide to trivalent phosphorus compounds and the inductive control in this initial step of the Staudinger reaction have been observed and discussed.