(ISOCYANOIMINO)TRIPHENYLPHOSPHORANE

Base Information

• Chemical Name: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE
• CAS No.: 73789-56-7
• Molecular Formula: C19H15 N2 P
• Molecular Weight: 302.315
• Hs Code.: 29319090
• European Community (EC) Number: 678-573-7
• DSSTox Substance ID: DTXSID10460651
• Nikkaji Number: J1.078.415H,J1.296.091C
• NSC Number: 371099
• Wikidata: Q82284792
• Mol file: 73789-56-7.mol

Synonyms:Isocyanamide,(triphenylphosphoranylidene)- (9CI); (Isocyanimino)triphenylphosphorane;(Isocyanoimino)triphenylphosphorane; NSC 371099

Chemical Property of (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE

Chemical Property:

• Melting Point: 160-161 °C
• PSA: 22.17000
• LogP: 3.22910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 302.097285485
• Heavy Atom Count: 22
• Complexity: 391

Purity/Quality:

97% ^*data from raw suppliers

(Isocyanoimino)triphenylphosphorane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [C-]#[N+]N=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• General Description: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE is a reactive phosphorane reagent used in multicomponent reactions to synthesize heterocyclic compounds, such as 2-aryl-5-hydroxyalkyl-1,3,4-oxadiazoles. It reacts with aldehydes and carboxylic acids under mild, neutral conditions to form these pharmacologically relevant structures in high yields (80–87%) without requiring additional activation. This reagent enables efficient and straightforward access to biologically active 1,3,4-oxadiazoles, making it valuable for synthetic and medicinal chemistry applications.

Technology Process of (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE

There total 3 articles about (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

triphenylphosphine (603-35-0) + formic acid hydrazide (624-84-0) → N-isocyaniminotriphenylphosphorane (73789-56-7)

Guidance literature:

With tetrachloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In acetonitrile; at 50 ℃; for 2h;

DOI:10.1055/s-2004-834928

Reference yield: 40.0%

triphenylphosphine (603-35-0) + formic acid hydrazide (624-84-0) → N-isocyaniminotriphenylphosphorane (73789-56-7) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With tetrachloromethane; triethylamine; In dichloromethane; at 50 - 60 ℃;

DOI:10.1002/ejic.200500196

Reference yield:

bis(trimethylsilyl)diazomethane (30006-66-7) + triphenylphosphine (603-35-0) → N-isocyaniminotriphenylphosphorane (73789-56-7)

Guidance literature:

In tetrahydrofuran; hexachloroethane; for 18h;

DOI:10.1016/0022-328X(89)80114-7

upstream raw materials:

bis(trimethylsilyl)diazomethane

triphenylphosphine

formic acid hydrazide

Downstream raw materials:

N-(triphenylphosphoranylidene)cyanamide

2-(2-aminophenyl)-1,3,4-oxadiazole

Refernces

Reaction between N-isocyaniminotriphenylphosphorane, aldehydes, and carboxylic acids: A one-pot and three-component synthesis of 2-aryl-5-hydroxyalkyl-1,3,4-oxadiazoles

10.1055/s-0029-1217337

The research focuses on the one-pot, three-component synthesis of 2-aryl-5-hydroxyalkyl-1,3,4-oxadiazoles, which are potentially synthetically and pharmacologically interesting compounds. The purpose of this study is to develop an efficient and facile method for the preparation of these biologically active heterocyclic compounds. The researchers used N-isocyaniminotriphenylphosphorane (NCNPPh3), an aldehyde, and a carboxylic acid as the key reactants in a 1:1:1 addition reaction under mild conditions. The process yielded the title compounds in good yields (80–87%) and was conducted under neutral conditions without the need for any activation or modification of the starting materials. The simplicity and good yields of this method make it an attractive alternative for the synthesis of 1,3,4-oxadiazoles, which may have applications in synthetic organic, bioorganic, and medicinal chemistry.