2327-67-5

Basic information

• Product Name: N-(triphenylphosphoranylidene)-p-toluidine
• Synonyms: N-(triphenylphosphoranylidene)-p-toluidine;(4-Methylphenylimino)triphenylphosphorane;N-(Triphenylphosphoranylidene)-4-methylaniline;Triphenyl-N-p-tolylphosphine imide;(4-methylphenyl)imino-triphenyl-$l^{5}-phosphane
• CAS NO: 2327-67-5
• Molecular Formula: C₂₅H₂₂NP
• Molecular Weight: 367.422641
• EINECS: 219-042-8
• Mol File: 2327-67-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 134-135 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 523.3°Cat760mmHg
• Flash Point: 270.3°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 1.6E-10mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: N-(triphenylphosphoranylidene)-p-toluidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(triphenylphosphoranylidene)-p-toluidine(2327-67-5)
• EPA Substance Registry System: N-(triphenylphosphoranylidene)-p-toluidine(2327-67-5)

Safety Data

• Hazardous Substances Data: 2327-67-5(Hazardous Substances Data)

Usage

General Description

N-(triphenylphosphoranylidene)-p-toluidine, also known as Wittig reagent, is an organophosphorus compound commonly used in organic synthesis as a reagent for the conversion of carbonyl compounds into alkenes. It is a highly reactive and versatile reagent, capable of yielding a wide variety of alkenes under mild reaction conditions. The compound is characterized by its triphenylphosphine group, which serves as an electrophilic carbon atom, enabling it to undergo nucleophilic attack by carbonyl compounds to form the corresponding alkene products. N-(triphenylphosphoranylidene)-p-toluidine has found widespread application in the synthesis of natural products, pharmaceuticals, and other complex organic molecules due to its efficiency and selectivity in alkene formation.

InChI:InChI=1/C25H22NP/c1-21-17-19-22(20-18-21)26-27(23-11-5-2-6-12-23,24-13-7-3-8-14-24)25-15-9-4-10-16-25/h2-20H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 2101-86-2 p-methylazidobenzene 
• 603-35-0 triphenylphosphine 
• 106-49-0 p-toluidine 
• 1034-39-5 dibromotriphenylphosphorane 
• 485842-65-7 dimethyl 2-(4-methylanilino)-3-(triphenylphosphoranylidene)butanedioate 
• 5758-24-7 bromotriphenylphosphonium bromide 

Downstream Products

• 3878-45-3 triphenylphosphine sulfide 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 622-58-2 p-Tolylisocyanate 
• 791-28-6 Triphenylphosphine oxide 
• 54378-35-7 C₂₅H₂₂NO₃PS 
• 54378-82-4 C-Methanesulfonyl-N-p-tolyl-C-(triphenyl-λ⁵-phosphanylidene)-methanesulfonamide 
• 54378-81-3 C₂₇H₂₆NO₄PS₂ 
• 54378-80-2 Triphenylphosphoniomethansulfonat 
• 5434-03-7 phenylmethanesulfon-p-toluidide 
• 54378-83-5 C₃₉H₃₄NO₄PS₂ 
• 54378-84-6 C₂₅H₂₁O₃PS 
• 726-42-1 di-p-tolylcarbodiimide 
• 85526-28-9 3-(4-Methylphenylimino)-1,2-diphenyl-2-propen-1-on 
• 85526-30-3 1,2-Bis(4-chlorphenyl)-3-(4-methylphenylimino)-2-propen-1-on 

Relevant articles and documents

Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones

A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Br?nsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.

Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: An efficient synthesis of aryliminophosphoranes under neutral and mild conditions

An efficient synthesis of aryliminophosphoranes is described. A mixture of an aromatic amine, diethyl azodicarboxylate and triphenylphosphine undergo a Mitsonobu type reaction at ambient temperature in dry dichloromethane to afford aryliminophosphoranes in excellent yields.

Selective synthesis of 4-alkylidene-β-lactams and N,N′- diarylamidines from azides and aryloxyacetyl chlorides via a ketenimine-participating one-pot cascade process

(Chemical Equation Presented) A one-pot cascade approach to 4-alkylidene-β-lactams and N,N-diarylamidines from aryl azides and aryloxyacetyl chlorides has been developed. The chemical outcome of the reaction can be controlled selectively by an appropriate choice of the stoichiometric ratio of different substrates and reagents. The products should find use in pharmaceutical discovery, especially in the development of new antimicrobial agents against multidrug-resistant pathogens.