73789-56-7

Basic information

• Product Name: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE
• Synonyms: Nsc371099;(ISOCYANOIMINO)TRIPHENYLPHOSPHORANE;1-methylidyne-2-(triphenyl-lambda~5~-phosphanylidene)diazanium;(N-Isocyanoimino)triphenylphosphorane 95%;(N-Isocyanoimino)Triphenylphosphorane;(N-Isocyanoi
• CAS NO: 73789-56-7
• Molecular Formula: C₁₉H₁₅N₂P
• Molecular Weight: 302.309561
• Mol File: 73789-56-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 160-161 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE(CAS DataBase Reference)
• NIST Chemistry Reference: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE(73789-56-7)
• EPA Substance Registry System: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE(73789-56-7)

Safety Data

• Hazardous Substances Data: 73789-56-7(Hazardous Substances Data)

Usage

Uses

Despite growing interest for therapeutic and other biological applications, cyclic peptidomimetics are challenging to synthesize. As reported by the lab of Andrei Yudin, (N-isocyanoimino)triphenylphosphorane (Pinc) enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. Containing a 1,3,4-oxadiazole, the resulting peptide exhibits both improved membrane permeability, lipophilicity, and aqueous solubility.Different functional groups can be introduced by varying the aldehyde, and initial work used propionaldehyde (538124), phenylacetaldehyde (107395), and isovaleraldehyde (146455).

InChI:InChI=1/C19H16N2P/c1-20-21-22(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19/h1-16H/q+1

Upstream product

• 603-35-0 triphenylphosphine 
• 624-84-0 formic acid hydrazide 
• 30006-66-7 bis(trimethylsilyl)diazomethane 

Downstream Products

• 5378-34-7 2-(3-bromophenyl)-1,3,4-oxadiazole 
• 41420-90-0 2-(4-bromophenyl)-1,3,4-oxadiazole 
• 5378-33-6 2-(3-chlorophenyl)-1,3,4-oxadiazole 
• 23289-10-3 2-(4-chlorophenyl)-1,3,4-oxadiazole 
• 41421-00-5 2-(m-tolyl)-1,3,4-oxadiazole 
• 827-58-7 2-p-tolyl-1,3,4-oxadiazole 
• 825-56-9 2-phenyl-1,3,4-oxadiazole 
• 1181289-27-9 C₁₅H₁₀FN₃O₄ 
• 1181289-29-1 C₁₅H₁₁BrN₂O₂ 
• 1181289-22-4 2-(4-bromophenyl)-5-(1-hydroxyethyl)-1,3,4-oxadiazole 
• 1181289-28-0 5-[1-hydroxy-1-(3-nitrophenyl)methyl]-2-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 1181289-26-8 2-[4-(dimethylamino)phenyl]-5-(1-hydroxybutyl)-1,3,4-oxadiazole 
• 1181289-25-7 C₁₅H₁₁ClN₂O₂ 
• 1181289-23-5 C₁₁H₁₂N₂O₂ 

Relevant articles and documents

An improved synthesis of N-isocyanoiminotriphenylphosphorane and its use in the preparation of diazoketones

An improved synthesis of N-isocyanoiminotriphenylphosphorane is reported. This reagent is a safe, stable, solid alternative to diazomethane and TMS-diazomethane in the Arndt-Eistert synthesis of diazoketones.

Silver-Catalyzed Cascade Reaction of N-Isocyaniminotriphenylphosphorane with Aldehydes: Synthesis of Unsymmetrical Azines

A direct synthesis of azines from the silver catalyzed domino interaction of N-isocyaniminotriphenylphosphorane and aldehydes is reported. The reaction proceeds through a tandem aza-Wittig, insertion, intramolecular cyclization and ring-opening processes.

Four-component synthesis of disubstituted 1,3,4-oxadiazoles from N-isocyaniminotriphenylphosphorane, phenylacetylenecarboxylic acid, chloroacetone derivatives, and primary amines

The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone derivatives is trapped by N-isocyaniminotriphenylphosphorane in the presence of phenylacetylenecarboxylic acid, leading to the formation of the corresponding iminophosp