2397-47-9

Basic information

• Product Name: triethyl phenylphosphorimidate
• CAS NO: 2397-47-9
• Molecular Formula: C₁₂H₂₀NO₃P
• Molecular Weight: 257.2659
• Mol File: 2397-47-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 305.3°C at 760 mmHg
• Flash Point: 138.4°C
• Density: 1.07g/cm³
• Vapor Pressure: 0.0015mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: triethyl phenylphosphorimidate(CAS DataBase Reference)
• NIST Chemistry Reference: triethyl phenylphosphorimidate(2397-47-9)
• EPA Substance Registry System: triethyl phenylphosphorimidate(2397-47-9)

Safety Data

• Hazardous Substances Data: 2397-47-9(Hazardous Substances Data)

Usage

General Description

Triethyl phenylphosphorimidate is a chemical compound consisting of a phosphorus atom bound to three ethyl groups and a phenyl group. It is commonly used in organic synthesis as a versatile reagent for the synthesis of phosphor-imidate derivatives of nucleic acids and other biologically active compounds. Triethyl phenylphosphorimidate is often used in the solid-phase synthesis of oligonucleotides, where it acts as a phosphitylating agent to form phosphodiester linkages between nucleotide units. Additionally, it can also be utilized as a coupling reagent in the synthesis of peptide nucleic acids. Overall, triethyl phenylphosphorimidate plays a crucial role in the production of a wide range of functional molecules and biomolecules with applications in biology, medicine, and material science.

Upstream product

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

Downstream Products

• 25626-89-5 O,O-diethyl-N-ethyl-N-phenyl-phosphoramidate 
• 61278-91-9 diethyl butyl(phenyl)phosphoramidate 
• 137957-76-7 Ethyl-phenyl-phosphoramidic acid dibutyl ester 
• 73732-37-3 Butyl-phenyl-phosphoramidic acid dibutyl ester 
• 133827-74-4 C₉H₅⁽²⁾H₉NO₃P 
• 73755-65-4 (OC₂H₅)2P(O)N(C₂H₅)C₆H₅(BF₃) 
• 36894-92-5 diethyl (N-acetyl-N-phenylamido)phosphate 
• 1445-38-1 diethyl phenylphosphoramidate 

Relevant articles and documents

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.

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.