13024-84-5

Basic information

• Product Name: dibutyl phenylphosphoramidate
• Synonyms: Dibutyl phenylphosphoramidate; phosphoramidic acid, N-phenyl-, dibutyl ester
• CAS NO: 13024-84-5
• Molecular Formula: C₁₄H₂₄NO₃P
• Molecular Weight: 285.319
• Mol File: 13024-84-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 355.4°C at 760 mmHg
• Flash Point: 168.7°C
• Density: 1.091g/cm³
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: dibutyl phenylphosphoramidate(CAS DataBase Reference)
• NIST Chemistry Reference: dibutyl phenylphosphoramidate(13024-84-5)
• EPA Substance Registry System: dibutyl phenylphosphoramidate(13024-84-5)

Safety Data

• Hazardous Substances Data: 13024-84-5(Hazardous Substances Data)

Usage

General Description

Dibutyl phenylphosphoramidate is a chemical compound with the molecular formula C14H24NO2P. It is a phosphoramidate compound containing a phenyl group and two butyl groups. dibutyl phenylphosphoramidate is commonly used as a catalyst and a reagent in organic synthesis and polymerization processes. It is a colorless to pale yellow liquid with a slight ammonia-like odor and is insoluble in water but soluble in organic solvents. Dibutyl phenylphosphoramidate is known for its ability to efficiently catalyze a wide range of reactions, including esterification, transesterification, and polymerization, making it a valuable tool in organic chemistry and industrial applications.

Upstream product

• 1809-19-4 dibutyl hydrogen phosphite 
• 62-53-3 aniline 
• 102-85-2 tri-n-butyl phosphite 
• 54635-88-0 phenyl-imidophosphoric acid tributyl ester 
• 819-43-2 dibutyl chlorophosphate 

Relevant articles and documents

Kinetics and mechanism of the anilinolysis of dibutyl chlorophosphate in acetonitrile

The nucleophilic substitution reactions of dibutyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 °C. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.86-0.97) with the strongly basic anilines while primary normal (kH/kD = 1.04-1.10) with the weakly basic anilines. The DKIEs, steric effects of the two ligands, activation parameters, cross-interaction constants, variation trends of the kH/kD values with X, and mechanism are discussed for the anilinolyses of the nine (R1O)(R2O)P(=O)Cl-type chlorophosphates. A concerted mechanism is proposed with a backside nucleophilic attack transition state for the strongly basic anilines and with a frontside attack involving a hydrogen-bonded four-center-type transition state for the weakly basic anilines on the basis of the magnitudes, secondary inverse and primary normal, and variation trends of the kH/kD values with X.

Kinetics and mechanism of anilinolysis of phenyl n-phenyl phosphoramidochloridate in acetonitrile

The kinetic studies on the reactions of phenyl N-phenyl phosphoramidochloridate (8) with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) have been carried out in acetonitrile at 60.0 oC. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are huge secondary inverse (kH/kD = 0.52-0.69). A concerted mechanism is proposed with a backside attack transition state (TS) on the basis of the secondary inverse DKIEs and the variation trends of the kH/kD values with X. The degree of bond formation in the TS is really extensive taking into account the very small values of the DKIEs. The steric effects of the two ligands on the rates are extensively discussed for the aminolyses of the chlorophosphate-type substrates on the basis of the Taft equation.

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.