57114-54-2

Basic information

• Product Name: trimethyl(phenylimino)-lambda~5~-phosphane
• CAS NO: 57114-54-2
• Molecular Formula: C₉H₁₄NP
• Molecular Weight: 167.1879
• Mol File: 57114-54-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 242.1°C at 760 mmHg
• Flash Point: 100.2°C
• Density: 0.97g/cm³
• Vapor Pressure: 0.0537mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: trimethyl(phenylimino)-lambda~5~-phosphane(CAS DataBase Reference)
• NIST Chemistry Reference: trimethyl(phenylimino)-lambda~5~-phosphane(57114-54-2)
• EPA Substance Registry System: trimethyl(phenylimino)-lambda~5~-phosphane(57114-54-2)

Safety Data

• Hazardous Substances Data: 57114-54-2(Hazardous Substances Data)

Upstream product

• 622-37-7 Phenyl azide 
• 594-09-2 trimethylphosphane 

Downstream Products

• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 3422-01-3 tert-butyl phenylcarbamate 

Relevant articles and documents

Mechanism and stereoselectivity of the aza-Wittig reaction between phosphazenes and aldehydes

The mechanism of the aza-Wittig reaction between phosphazenes and aldehydes has been studied computationally, using DFT methods (B3LYP/6-31G* level), and experimentally. It has been found that the reaction consists of a tandem [2+2] cycloaddition-cycloreversion sequence in which π and σ orbitals as well as lone pairs are involved. Both [2+2] processes take place via thermally allowed supra-supra mechanisms. P-trimethyl-λ5- phosphazenes are predicted to be more reactive than their P-triphenyl analogues. The stereochemical outcome of the whole reaction depends only on the second step, because conformational changes in the intermediate 1,3,2- λ5-oxazaphosphazetidines have a much lower activation energy than the second [2+2] cycloreversion reaction. Preferential or exclusive formation of the corresponding (E)-imines is predicted.