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3-Phenylquinoline is an organic compound with the molecular formula C19H13N. It is a derivative of quinoline, a heterocyclic aromatic compound, and features a phenyl group attached to the 3-position of the quinoline ring. 3-phenylquinoline is known for its potential applications in the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical structure. It is also used as an intermediate in the production of certain dyes and pigments. The compound is characterized by its yellow crystalline appearance and is typically synthesized through various chemical reactions, such as the Friedl?nder reaction, which involves the condensation of aniline with 2-acetylpyridine. 3-Phenylquinoline's properties, such as its reactivity and stability, make it a valuable building block in organic chemistry and a subject of interest in the development of new materials and compounds.

1666-96-2

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1666-96-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 1666-96-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,6 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1666-96:
(6*1)+(5*6)+(4*6)+(3*6)+(2*9)+(1*6)=102
102 % 10 = 2
So 1666-96-2 is a valid CAS Registry Number.

1666-96-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-phenylquinoline

1.2 Other means of identification

Product number -
Other names 3-phenyl-quinoline

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:1666-96-2 SDS

1666-96-2Relevant academic research and scientific papers

PALLADIUM-CATALYZED SYNTHESIS OF QUINOLINES FROM ALLYLIC ALCOHOLS AND o-IODOANILINE

Larock, Richard C.,Kuo, Mann-Yan

, p. 569 - 572 (1991)

The palladium-catalyzed coupling of allylic alcohols and o-iodoaniline provides a convenient, one-step synthesis of quinolines.

An isonitrile-alkyne cascade to di-substituted indoles

Rainier, Jon D.,Kennedy, Abigail R.,Chase, Eric

, p. 6325 - 6327 (1999)

Intramolecular tin and sulfur mediated free-radical cyclizations between an aryl isonitrile and a pendant TMS-substituted alkyne give 2,3- disubstituted indoles from 5-exo-dig cyclization and nucleophilic trapping of the resulting indolenine intermediate.

SBA-15-type organosilica with 4-mercapto-N,N-bis-(3-Si-propyl)butanamide for palladium scavenging and cross-coupling catalysis

El Hankari, Samir,El Kadib, Abdelkrim,Finiels, Annie,Bouhaouss, Ahmed,Moreau, Joel J.E.,Crudden, Cathleen M.,Brunel, Daniel,Hesemann, Peter

, p. 8984 - 8994 (2011)

This work describes the synthesis of novel functional silica materials with difunctional thiol-amide substructures and featuring regular architectures on a mesoscopic level. The functional materials were synthesised by both one-pot co-condensation and post-grafting approaches. The thiol groups confined in the matrix were found to be efficient for palladium entrapment, leading to highly active and reusable heterogeneous catalysts for Sonogashira and Suzuki-Miyaura cross-coupling reactions. This work evidences the crucial role of both the thiol precursor and the condensation degree of the silica scaffold in view of the design of stable and reusable tailor-made mesoporous catalytic silica materials.

Suzuki-miyaura cross-coupling reactions in a Solkane365/227/ethanol blend at ambient temperature

Xu, Xiu-Hua,Azuma, Ayaka,Kusuda, Akihiro,Tokunaga, Etsuko,Shibata, Norio

, p. 1504 - 1508 (2012)

An environmentally benign solvent system, Solkane365/227/ethanol blend, was developed for Suzuki-Miyaura cross-coupling reactions of aryl boronic acids and aryl halides. The reaction is quite general and gives excellent yields for various aryl, heteroaryl, and fluoroaryl boronic acids or halides. Interestingly, this system also allows the synthesis of polyaryls.

Imidazolium supported palladium-chloroglycine complex: Recyclable catalyst for Suzuki-Miyaura coupling reactions

Karthikeyan, Parasuraman,Vanitha, Arumugam,Radhika, Pachaiappan,Suresh, Kannan,Sugumaran, Arunachalam

, p. 7193 - 7197 (2013)

1-Glycyl-3-methyl imidazolium chloride-palladium(II) complex [[Gmim]Cl-Pd(II)] was found to be a catalyst for the Suzuki-Miyaura reaction with excellent yields with high turnover number (6.5 × 102-9.4 × 102).

PEPPSI-Pd-NHC catalyzed Suzuki-Miyaura cross-coupling reactions in aqueous media

Kalo?lu, Nazan,?zdemir, ?smail

, p. 2306 - 2313 (2019)

A series of unsymmetrical 1,3-disubstituted benzimidazolium chlorides were synthesized as N-heterocyclic carbene (NHC) precursors. These compounds were used to synthesize of the PEPPSI-type palladium NHC complexes. The structures of all compounds were cha

Pd Nanoparticles Dispersed on ZrIV Organophosphonate: A Robust and Reusable Catalyst for Suzuki–Miyaura Cross-Coupling Reactions

Borah, Suchibrata,Mishra, Shashank,Cardenas, Luis,Gogoi, Nayanmoni

, p. 751 - 758 (2018)

A mesoporous zirconium(IV) phosphonate was synthesized by the hydrothermal reaction of ZrOCl2·8H2O with a trisphosphonic acid ligand, mesityl-1,3,5-tris(methylenephosphonic acid). Treatment of the mesoporous ZrIV phosphonate framework with Pd(OAc)2 and subsequent reduction produced a nanocomposite where Pd nanoparticles of average size ca. 7–8 nm were found to be homogeneously and abundantly dispersed over the phosphonate framework. The composite acts as an efficient and reusable heterogeneous catalyst in the Suzuki–Miyaura cross coupling reaction of aryl bromides with aryl boronic acids.

Copper-catalyzed synthesis of substituted quinolines via C-N coupling/condensation from ortho -acylanilines and alkenyl iodides

Kong, Lingkai,Zhou, Yuanyuan,Huang, He,Yang, Yang,Liu, Yuanyuan,Li, Yanzhong

, p. 1275 - 1278 (2015)

An efficient cascade copper-catalyzed intermolecular Ullmann-type C-N coupling/enamine condensation reaction is described, in which ortho-acylanilines and alkenyl iodides converted to multisubstituted quinolines in good to excellent yields.

Reusable polymer-supported palladium catalysts: An alternative to tetrakis(triphenylphosphine)palladium in the suzuki cross-coupling reaction

Fenger, Isabelle,Le Drian, Claude

, p. 4287 - 4290 (1998)

The Suzuki cross-coupling reaction of a boronic acid and a bromoaromatic requires palldium catalysis. Almost identical yields were obtained in the usual conditions, with 30 mequiv. of Pd(PPh3)4, and with 2 mequiv of a polymer-supported catalyst, which was easily prepared in two steps from Merrified polymer. Recovery and reuse of the catalyst is easy, and only 0.60% of the initial amount of palladium is lost during a reaction.

From the grafting of NHC-based Pd(II) complexes onto TiO2 to the in situ generation of Mott-Schottky heterojunctions: The boosting effect in the Suzuki-Miyaura reaction. Do the evolved Pd NPs act as reservoirs?

De Tovar, Jonathan,Rataboul, Franck,Djakovitch, Laurent

, p. 133 - 147 (2021/05/10)

The assumption that the real active species involved in the Suzuki-Miyaura reaction are homogeneous, heterogeneous or both is often proposed. However a lack of characterization of the true catalytic entities and their monitoring makes assumptions somewhat elusive. Here, with the aim of getting new insights into the formation of active species in the Suzuki-Miyaura reaction, a family of palladium(II) complexes bearing bis(NHC) ligands was synthesized for immobilization at the surface of TiO2. The studies reveal that once the complexes are anchored onto TiO2, the mechanism governing the catalytic reaction is different from that observed for the non-anchored complexes. All complexes evolved to Pd NPs at the surface of TiO2 under reaction conditions and released Pd species in the liquid phase. Also, this reactivity was boosted by the in situ generation of Mott-Schottky heterojunctions, opening new routes towards the design of heterogenized catalysts for their further implementation in reverse-flow reactors.

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