N-(triphenyl-λ5-phosphanylidene)aniline

• ChemBase ID: 147488
• Molecular Formular: C24H20NP
• Molecular Mass: 353.396061
• Monoisotopic Mass: 353.13333628
• SMILES: c1ccc(cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H20NP/c1-5-13-21(14-6-1)25-26(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
• InChIKey: PTLOPIHJOPWUNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(triphenyl-λ^5-phosphanylidene)aniline
• IUPAC Traditional name: N-(triphenyl-λ^5-phosphanylidene)aniline
• Synonyms: Anilidenetriphenylphosphorane; Tetraphenylphosphine imide; N-(Triphenylphosphoranylidene)aniline; N-(Triphenylphosphoranylidene)aniline; Tetraphenylphosphine imide; 四苯基亚胺膦; 四苯基氨化膦

Database IDs

• CAS Number: 2325-27-1
• EC Number: 219-039-1
• MDL Number: MFCD00003044
• Beilstein Number: 753032
• PubChem SID: 24859473; 162241676
• PubChem CID: 75352

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.2806935
• LogD (pH = 7.4): 7.2808976
• Log P: 7.2809
• Molar Refractivity: 111.8114 cm^3
• Polarizability: 43.10562 Å^3
• Polar Surface Area: 12.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 128-132°C

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Impurities: <0.5% denatured ethanol
• Linear Formula: (C6H5)3P=NC6H5

DETAILS

Sigma Aldrich - 324876

Packaging
5 g in glass bottle
Application
The Staudinger Ligation: A High-Yield, Chemoselective, and Mild Synthetic MethodIntermediate for the preparation of isocyanates and isothiocyanates.

REFERENCES

• Has been used as a protected form of aniline for the preparation of monoalkylanilines by alkylation and hydrolysis: Synthesis, 295 (1980).
• A Wittig-like reaction with N,N'-diaryl thioureas gives N,N',N"-triarylguanidines: Synth. Commun., 13, 67 (1983).
• For a review of the chemistry of iminophosphoranes, see: Synthesis, 469 (1973).