(N-Isocyanoimino)triphenylphosphorane

ALDRICH/900555 - 95%

Synonym: Pinc

CAS Number: 73789-56-7
Empirical Formula (Hill Notation): C₁₉H₁₅N₂P
Molecular Weight: 302.31
MDL Number: MFCD09038528
Linear Formula: C₁₉H₁₅N₂P
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-900555-5G	5 g	$412.00 1/EA	Add To Favorites

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Properties
Descriptions
Safety Info.
Basic Data

application(s)	peptide synthesis
assay	95%
form	solid
InChI	1S/C19H15N2P/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/h2-16H
InChI key	NIDTXBFHPXMXTR-UHFFFAOYSA-N
Quality Level	100
SMILES string	[P](=N[N+]#[C-])(c3ccccc3)(c2ccccc2)c1ccccc1

Application:	As reported by the lab of Andrei Yudin , Pinc enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. It enables the formation of disubstituted 1,3,4-oxadiazoles by intercepting the key mixed anhydride characteristic of the Ugi reaction. Furthermore, the resulting peptide macrocycles containing oxadiazole exhibit improved drug properties such as cell-permeability and a rigid conformation.
Features and Benefits:	• Bench-stable solid: Pinc is a stable reagent that can be easily handled and stored. • Facilitates cyclization and incorporation of conformational control element: Pinc enables the formation of peptide macrocycles with a desired conformation, leading to improved drug properties. • Amphoteric properties: Pinc′s amphoteric nature allows for the design of new multicomponent reactions, expanding its synthetic capabilities. • Desired drug properties: The resulting peptide macrocycles exhibit enhanced membrane permeability, lipophilicity, and aqueous solubility, making them desirable for drug development. • Versatile transformations: Pinc′s ability to form oxadiazoles opens up opportunities for the development of novel synthetic transformations.
General description:	(N-Isocyanoimino)triphenylphosphorane (Pinc) is a bench-stable solid reagent widely used in organic synthesis. It is an amphoteric compound with unique properties that make it a versatile tool for various applications, including heterocycle synthesis and macrocyclization of peptides. Pinc facilitates cyclization and incorporation of a conformational control element into peptide macrocycles, leading to desired drug properties such as improved membrane permeability, lipophilicity, and aqueous solubility. Its ability to form oxadiazoles offers opportunities for the development of new transformations.
Packaging:	5 g in glass bottle
Packaging:	500 mg in glass insert

Symbol	GHS07
Signal word	Warning
Hazard statements	H315 - H319 - H335
Precautionary statements	P302 + P352 - P305 + P351 + P338
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	95%
UNSPSC	12352209

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