(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:

99% ^*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
• 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).

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-(3-bromophenyl)-1,3,4-oxadiazole

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

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

Refernces

• 1、 Souldozi, Ali,Karami, Samad. "One-pot three-component reaction for the synthesis of novel series of fully substituted 1,3,4-oxadiazole derivatives bearing pyridine moiety". . p. 867 - 870. Retrieved 2016.
• 2、 Chen, Lingnan,Cao, Shanshan,Zhang, Jingping,Wang, Zikun. "Silver-promoted regio- and stereoselective aminocyanation of alkynes for the synthesis of β-aminoacrylonitriles using N-isocyanoiminotriphenylphosphorane". supporting information. p. 1678 - 1681. Retrieved 2019/05/29.