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(Isocyanoimino)triphenylphosphorane, also known as Pinc, is a chemical compound that plays a crucial role in the synthesis of cyclic peptidomimetics. It is a versatile reagent that enables the zwitterionic-controlled generation of peptide macrocycles from linear peptides and aldehydes, resulting in a 1,3,4-oxadiazole-containing peptide with improved membrane permeability, lipophilicity, and aqueous solubility.

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  • 73789-56-7 Structure
  • Basic information

    1. Product Name: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE
    2. Synonyms: Nsc371099;(ISOCYANOIMINO)TRIPHENYLPHOSPHORANE;1-methylidyne-2-(triphenyl-lambda~5~-phosphanylidene)diazanium;(N-Isocyanoimino)triphenylphosphorane 95%;(N-Isocyanoimino)Triphenylphosphorane;(N-Isocyanoi
    3. CAS NO:73789-56-7
    4. Molecular Formula: C19H15N2P
    5. Molecular Weight: 302.309561
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 73789-56-7.mol
  • Chemical Properties

    1. Melting Point: 160-161 °C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE(CAS DataBase Reference)
    10. NIST Chemistry Reference: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE(73789-56-7)
    11. EPA Substance Registry System: (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE(73789-56-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 73789-56-7(Hazardous Substances Data)

73789-56-7 Usage

Uses

Used in Pharmaceutical Industry:
(Isocyanoimino)triphenylphosphorane is used as a key reagent for the synthesis of cyclic peptidomimetics, which are essential in the development of novel therapeutic agents. (ISOCYANOIMINO)TRIPHENYLPHOSPHORANE facilitates the formation of peptide macrocycles from linear peptides and aldehydes, leading to the creation of more effective and stable drug candidates.
Used in Research and Development:
In the field of research and development, (Isocyanoimino)triphenylphosphorane is used as a valuable tool for the synthesis of various cyclic peptidomimetics with different functional groups. By varying the aldehyde used in the reaction, researchers can introduce different functional groups and explore the potential applications of these modified peptidomimetics in various biological and therapeutic contexts.
Used in Drug Design and Synthesis:
(Isocyanoimino)triphenylphosphorane is employed as a critical component in the design and synthesis of cyclic peptidomimetics with enhanced properties. The improved membrane permeability, lipophilicity, and aqueous solubility of the resulting peptides make them more suitable for drug development, potentially leading to the creation of more effective treatments for various diseases and conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 73789-56-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,7,8 and 9 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 73789-56:
(7*7)+(6*3)+(5*7)+(4*8)+(3*9)+(2*5)+(1*6)=177
177 % 10 = 7
So 73789-56-7 is a valid CAS Registry Number.
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

73789-56-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (Isocyanoimino)triphenylphosphorane

1.2 Other means of identification

Product number -
Other names isocyanoimino(triphenyl)-λ<sup>5</sup>-phosphane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:73789-56-7 SDS

73789-56-7Relevant articles and documents

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

Bio, Matthew M.,Javadi, Gary,Song, Zhiguo Jake

, p. 19 - 21 (2005)

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.

One-pot three-component reaction for the synthesis of novel series of fully substituted 1,3,4-oxadiazole derivatives bearing pyridine moiety

Souldozi, Ali,Karami, Samad

, p. 867 - 870 (2016)

(N-isocyanimino)triphenylphosphorane, 2-pyridinecarbaldehyde, and aromatic carboxylic acids (benzoic acid, 3-methylbenzoic acid, 4-methylbenzoic acid, 3-methoxybenzoic acid, 1-naphthoic acid, and 2- naphthoic acid) undergo a 1:1:1 addition reaction underm

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

Wang, Yeming,Yu, Yang,Zhao, Liping,Ning, Yongquan

, p. 7237 - 7239 (2019)

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.

Silver-promoted regio- and stereoselective aminocyanation of alkynes for the synthesis of β-aminoacrylonitriles using N-isocyanoiminotriphenylphosphorane

Chen, Lingnan,Cao, Shanshan,Zhang, Jingping,Wang, Zikun

supporting information, p. 1678 - 1681 (2019/05/29)

The silver-promoted intermolecular aminocyanation of alkynes for the synthesis of (Z)-β-aminoacrylonitriles is reported, using N-isocyanoiminotriphenylphosphorane (NIITP) as both the nitrile and amine source. The transformation proceeds in moderate to good yields, and in a regio- and stereoselective manner, using a wide range of acetylenes.

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

Ramazani, Ali,Nasrabadi, Fatemeh Zeinali,Karimi, Zahra,Rouhani, Morteza

, p. 1818 - 1830 (2013/05/21)

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

Free and metal-coordinated (N-isocyanimino)triphenylphosphorane: X-ray structures and selected reactions

Stolzenberg, Heribert,Weinberger, Bernd,Fehlhammer, Wolf Peter,Puehlhofer, Frank G.,Weiss, Robert

, p. 4263 - 4271 (2007/10/03)

An improved procedure for the synthesis of (N-isocyanimino)- triphenylphosphorane, C≡N-N=PPh3 (3), is described. The X-ray structure analysis reveals an unusually small N-N=P angle [115.2(2)°] and an N-N bond order of only about 1.5, which indicates considerable C≡N-N --P+ participation and electronically more-isolated functional groups (CN, P=N) in the isocyanide than, for example, in the isomeric N≡C-N=PPh3 (4) [C-N=P = 123.0(4)°, C-N bond order = 2.0]. In order to gain insight into the stereochemical consequences of metal coordination of 3, an X-ray structural study of [Cr-(CO)5C≡N-N= PPh3] (5) was also undertaken. Surprisingly, the central bond lengths (C-N, N-N) and angles (C-N-N) remain practically unchanged with noticeable coordination effects occurring only at the periphery of 5, with the N-N-P angle [112.3(2)°] further decreased by 15σ, the elongated (by 7σ) P-N bond, the somewhat shortened (by 4σ) P-C(Ph) bonds and even shorter C-H(Ph) bonds on the one side, and the well-known Cr-C(O)trans contraction on the other. Treatment of 5 or its tungsten derivative with anhydrous Bronstedt and Lewis acids such as CF3COOH, HCl, COS, phosgene or, most efficiently, [PdCl2(1,5-COD)] causes CN→NC isomerisation to give [M(CO)5N≡C-N=PPh3] [M = Cr (6), W (7)]. In solution, [PdCl2(CNNPh3)2] and Ph3BCNNPPh3 (8) slowly isomerize even without additional acid to give both free and Pd-coordinated 4 and Ph3BNCNPPh 3 (9), respectively. In the presence of catalytic amounts of [PdCl2(1,5-COD)], 3 is converted into 4 and the dimer Ph 3PN-C(CN)=N-NPPh3 (10) in an almost 1:1 ratio. The optimised geometries of the methyl derivatives of 3 and 4, namely Me 3P=N-N≡C (3c) and Me3P=N-C≡N (4c), are in excellent agreement with the experimental data; major differences between the isomers (P-N-N angle, N-N bond length) are explained by the higher electronegativity of the isocyano group as compared to the CN substituent, which, in turn, is a better π-acceptor). The reaction path of the isomerisation of 3 to 4 (3c to 4c) has also been studied computationally and been found to proceed via an [(P)=NA-N≡CA(N A-CA)] cyclic transition state. The overall process is exothermic by 50 kcal mol-1. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Reactions of bis(trimethylsilyl)isocyanamide and its isomers with chlorotriphenylphosphonium chloride: evidence for a transient dizomethylenetriphenylphosphorane. Crystal structure of NN->2

Zinner, Gerhard,Beck, Gerhard,Fehlhammer, Wolf P.,Wiberg, Nils

, p. 23 - 30 (2007/10/02)

Triphenylphosphine dichloride reacts with (Me3Si)2C=NN, Me3SiN=C=NSiMe3, and metal-coordinated CN-N(SiMe3)2 to give the iminophosphoranes CN-NPPh3, NC-NPPh3, and W(CO)5CN-NPPh3, respectively, and with free bis(trimethylsilyl)isocyanamine to give a dicatio

Metal Complexes of Functional Isocyanides, VIII: (Isocyanoimino)triphenylphosphorane Metal Complexes

Weinberger, Bernd,Fehlhammer, Wolf Peter

, p. 42 - 50 (2007/10/02)

The thermally unusually stable N-isocyanide CNNPPh3 (1) is prepared by the reaction of formylhydrazine with triphenylphosphane, tetrachloromethane, and triethylamine and reacted with metal compounds to give the complexes M(CO)5CNNPPh3 (M = Cr, Mo, W) (3-5), cis-Cr(CO)4(CNNPPh3)2 (6), Mn(η-C5H5)(CO)2CNNPPh3 (7), PF6 (8), PdX2(CNNPPh3)2 (X = Cl, I) (9a,b), cis-BF4 (11), and trans-2 (12).

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