14562-02-8

Basic information

• Product Name: (4-Nitrophenylimino)triphenylphosphorane
• Synonyms: (4-Nitrophenylimino)triphenylphosphorane;N-(4-Nitrophenyl)triphenylphosphine imide;N-(4-NITROPHENYL)-P,P,P-TRIPHENYLPHOSPHINE IMIDE;(4-nitrophenyl)imino-triphenyl-$l^{5}-phosphane
• CAS NO: 14562-02-8
• Molecular Formula: C₂₄H₁₉N₂O₂P
• Molecular Weight: 398.3936
• Mol File: 14562-02-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 574°Cat760mmHg
• Flash Point: 300.9°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 1.39E-12mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: (4-Nitrophenylimino)triphenylphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Nitrophenylimino)triphenylphosphorane(14562-02-8)
• EPA Substance Registry System: (4-Nitrophenylimino)triphenylphosphorane(14562-02-8)

Safety Data

• Hazardous Substances Data: 14562-02-8(Hazardous Substances Data)

Usage

General Description

(4-Nitrophenylimino)triphenylphosphorane is a complex organic compound composed of a phosphorus atom bonded to three phenyl groups and an imino group containing a nitro group attached to a phenyl ring. It is used as a reagent in organic synthesis, particularly in the preparation of imines and related compounds. The imino group is reactive and can undergo various chemical reactions, making this compound useful in the formation of carbon-nitrogen and carbon-carbon bonds. Its structure and reactivity make (4-Nitrophenylimino)triphenylphosphorane a valuable tool in the field of organic chemistry for creating a diverse range of chemical compounds.

InChI:InChI=1/C24H19N2O2P/c27-26(28)21-18-16-20(17-19-21)25-29(22-10-4-1-5-11-22,23-12-6-2-7-13-23)24-14-8-3-9-15-24/h1-19H

Upstream product

• 100-01-6 4-nitro-aniline 
• 1034-39-5 dibromotriphenylphosphorane 
• 5758-24-7 bromotriphenylphosphonium bromide 
• 603-35-0 triphenylphosphine 
• 4756-25-6 (9H-fluoren-9-ylidene)triphenylphosphorane 
• 13165-67-8 N-sulphinyl-p-nitroaniline 
• 1516-60-5 4-nitrophenyl azide 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 

Downstream Products

• 22751-79-7 1,3-diphenylbenzo[e]-[1,2,4]triazin-7(1H)-one 
• 22731-52-8 N-(Diphenylethenylidene)-4-nitrobenzeneamine 
• 132316-04-2 {Rh(CO)2Cl(NO₂C₆H₄NP(C₆H₅)3)} 
• 132373-65-0 {Rh(C₈H₁₂)Cl(NO₂C₆H₄NP(C₆H₅)3)} 
• 74378-44-2 C₂₅H₂₂N₂O₂P⁽¹⁺⁾*I^(1-) 
• 86312-11-0 2-(p-nitrophenylimino)-3-phenyl-4-tosylimino-1,3-thiazetidine 
• 100-28-7 4-Nitrophenyl isocyanate 
• 2131-61-5 p-nitrophenyl isothiocyanate 
• 738-66-9 bis(p-nitrophenyl)carbodiimide 

Relevant articles and documents

Vinyltriphenylphosphonium salt mediated serendipitous synthesis of aryliminophosphoranes

Crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dimethyl acetylenedicarboxylate and aromatic amines, such as aniline, 1-naphthylamine, p-toluidine, 4-bromoaniline, 4-nitroaniline, 4-acetylaniline, 2-aminopyridine, or 2-amino-5-bromopyridine. These stabilized phosphoranes undergo a smooth intramolecular reaction in boiling p-xylene or toluene to produce aryliminophosphoranes in excellent yields.

Synthesis and structures of substituted triphen-yl(phenyl-imino)phospho- ranes

Three substituted triphen-yl(phenyl-imino)phospho-ranes, namely (4-cyano-phenyl-imino)triphenyl-phospho-rane, C25H19N 2P, (I), (4-nitro-phenyl-imino)triphenyl-phospho-rane, C 24H19N2O2P, (II), and (3-nitro-phenyl-imino)triphenyl-phospho-rane, C24H19N 2O2P, (III), were synthesized as precursors for the preparation of substituted diphenyl-carbodiimides. All three compounds display a supramolecular arrangement in which the substituted benzene rings are organized in an antiparallel fashion. The nitro group on the ring participates in C - H...O and O...π inter-actions, forming inter-molecular dimers. Compound (III) shows disorder which involves the rotation of one of the phenyl rings of the triphenyl-phosphine group.

PHOSPHORYLATION OF HETEROCYCLIC COMPOUNDS III. REACTIONS OF PHOSPHORYLATED 2,2,2,5-TETRAPHENYL-Δ4-1,3,4,2λ5-OXADIAZAPHOSPHOLINE WITH NUCLEOPHILES

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