772-03-2

Basic information

• Product Name: 2-VINYLQUINOLINE
• Synonyms: 2-Ethenylquinoline;2-Vinylquinoline, stabilized,99%;NSC 99356;2-VINYLQUINOLINE;2-ethenyl-quinolin;2-Vinylquinoline (stabilised);2-Vinylquinoline 97%
• CAS NO: 772-03-2
• Molecular Formula: C₁₁H₉N
• Molecular Weight: 155.2
• EINECS: 212-246-8
• Product Categories: monomer;Fused Ring Systems
• Mol File: 772-03-2.mol

Chemical Properties

• Melting Point: 284-285 °C
• Boiling Point: 269.01°C (rough estimate)
• Flash Point: 111.9 °C
• Appearance: dark orange-brown liquid
• Density: 1.0300
• Vapor Pressure: 0.0117mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: 2-8°C
• PKA: 4.88±0.40(Predicted)
• CAS DataBase Reference: 2-VINYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-VINYLQUINOLINE(772-03-2)
• EPA Substance Registry System: 2-VINYLQUINOLINE(772-03-2)

Safety Data

• Hazardous Substances Data: 772-03-2(Hazardous Substances Data)

Usage

Chemical Properties

dark orange-brown liquid

InChI:InChI=1/C11H9N/c1-2-10-8-7-9-5-3-4-6-11(9)12-10/h2-8H,1H2

Upstream product

• 1011-50-3 2-quinolin-2-yl-ethanol 
• 612-62-4 2-Chloroquinoline 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 5470-96-2 quinoline 2-carbaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2005-43-8 2-bromoquinoline 
• 75927-49-0 pinacol vinylboronate 
• 91-63-4 2-methylquinoline 
• 50-00-0 formaldehyd 
• 123-91-1 1,4-dioxane 
• 4363-34-2 vinylboronic acid 
• 1613-37-2 Quinoline N-oxide 
• 1826-67-1 vinyl magnesium bromide 
• 91-22-5 quinoline 

Downstream Products

• 102022-17-3 1-phenyl-4-(quinolin-2-yl)butan-1-one 
• 113039-53-5 4-[2]quinolyl-2-methyl-1-phenyl-butan-1-one 
• 47304-84-7 Diethyl-2-(2-guinoyl)ethylmalonat 
• 57961-89-4 2-[2-(4-phenyl-piperazin-1-yl)-ethyl]-quinoline 
• 57961-90-7 Centhaquin 
• 57962-04-6 1-(β-phenethyl)-4-(β-2-quinolylethyl)piperazine 
• 57961-96-3 2-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethyl}-quinoline 
• 57961-98-5 2-{2-[4-(2-chloro-phenyl)-piperazin-1-yl]-ethyl}-quinoline 
• 57961-94-1 2-{2-[4-(2-methoxy-phenyl)-piperazin-1-yl]-ethyl}-quinoline 
• 57962-01-3 2-{2-[4-(3,4-dichloro-phenyl)-piperazin-1-yl]-ethyl}-quinoline 
• 53981-06-9 benzyl-methyl-(2-quinolin-2-yl-ethyl)-amine 
• 57962-03-5 2-{2-[4-(3,4-dimethyl-phenyl)-piperazin-1-yl]-ethyl}-quinoline 
• 57962-06-8 2-{2-[4-(3-fluoro-phenyl)-piperazin-1-yl]-ethyl}-quinoline 
• 57962-07-9 2-{2-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethyl}-quinoline 

Relevant articles and documents

Mechanism and proton activating factors in the base-induced β-elimination reaction of N-[2-(2-quinolyl)ethyl]-quinuclidinium salt

N-[2-(2-Quinolyl)ethyl]quinuclidinium salt in OH--H2O, 50°C, μ = 1 M KCl undergoes an elimination reaction with formation of 2-vinylquinoline; the second-order rate constant is kN = 12.8 × 10-3 dm3 mol-1 s-1. In acetohydroxamic acid-acetohydroxamate buffers at pH 8-9 the β-elimination reaction occurs by a reversible E1cb mechanism, (E1Cb)R. In this process, carbon deprotonation occurs from the conjugate acid, protonated at the nitrogen atom of the quinoline ring, NH+; this species is present at a very low concentration with respect to the unprotonated substrate N, with pKa = 3.87 at 50°C, μ = 1 M KCl. The reason for the high reactivity of NH+ with respect to N is related to the high stability of the intermediate carbanion formed from NH+, which presents an enamine structure. Kinetic parameters from a study of acid-base catalysis can be calculated and compared with those of the related system activated by a pyridine ting. Studies of H/D exchange and solvent isotope effect are in agreement with the proposed mechanism. Copyright

Water-Sculpting of a Heterogeneous Nanoparticle Precatalyst for Mizoroki-Heck Couplings under Aqueous Micellar Catalysis Conditions

Powdery, spherical nanoparticles (NPs) containing ppm levels of palladium ligated by t-Bu3P, derived from FeCl3, upon simple exposure to water undergo a remarkable alteration in their morphology leading to nanorods that catalyze Mizoroki-Heck (MH) couplings. Such NP alteration is general, shown to occur with three unrelated phosphine ligand-containing NPs. Each catalyst has been studied using X-ray photoelectron spectroscopy (XPS), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), and cryogenic transmission electron microscopy (cryo-TEM) analyses. Couplings that rely specifically on NPs containing t-Bu3P-ligated Pd occur under aqueous micellar catalysis conditions between room temperature and 45 °C, and show broad substrate scope. Other key features associated with this new technology include low residual Pd in the product, recycling of the aqueous reaction medium, and an associated low E Factor. Synthesis of the precursor to galipinine, a member of the Hancock family of alkaloids, is suggestive of potential industrial applications.

The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan

The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.

SULFONYL-SUBSTITUTED BICYCLIC COMPOUND WHICH ACTS AS ROR INHIBITOR

Provided is a sulfonyl-substituted bicyclic compound (A) which acts as a RORγ inhibitor, said compound has good RORγ inhibitory activity and is expected to be used for treating diseases mediated by a RORγ receptor in mammals.

PYRAZOLOPYRIMIDINE PDE10 INHIBITORS

The present invention is directed to pyrazolopyrimidine compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

ARYLOXYMETHYL CYCLOPROPANE DERIVATIVES AS PDE10 INHIBITORS

The present invention is directed to aryloxymethyl cyclopropane derivatives which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines

Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.

Facile catalyst-free synthesis of 2-vinylquinolines via a direct deamination reaction occurring during Mannich synthesis

A facile catalyst-free method for the synthesis of 2-vinylquinolines via a direct deamination reaction during Mannich synthesis has been developed. Instantaneous hydrogen transfer via a six-membered ring intermediate is proposed as a key step for the direct deamination reaction. This reaction strategy tolerates a broad substrate scope and provides a highly efficient way to synthesize 2-vinylquinolines with adequate yields.

Synthesis and optoelectronic properties of phenylenevinylenequinoline macromolecules

A series of 3, 5 and 7 quinoline terminated arylenevinylene oligomers was selectively synthesized by applying two repetitive reactions at each cycle of oligomerization: a Wittig and Pd Heck cross-coupling. Oligomers were characterized by 1H and homo-J-resolved, DEPT-135, APT, 13C NMR and MALDI-TOF spectrometry. A detailed characterization of the oligomers was performed by UV-Vis, static-dynamic fluorescence and Z-scan spectroscopy. The HOMO and LUMO levels were determined by cyclic voltammetry and compared with the theoretical ones. Effective conjugation is attained for the pentamer, whilst the molecular structure of the heptamer shows a pronounced torsion of the phenylenevinylene segment disrupting the degree of conjugation as revealed by theoretical simulation of the oligomer geometry. Furthermore, the theoretical simulation shows that the HOMO-LUMO frontier orbitals are mainly localized in the phenylenevinylene structure, while in the quinolines the spatial distribution is only located at the CN- group without any appreciable contribution of the adjacent phenyl group. The pentamer is the most fluorescent oligomer with a quantum yield in solution of = 0.62-0.68 depending on the solvent and a fluorescence lifetime of 1.07-1.28 ns, making this oligomer suitable for optoelectronic devices.

Iron-catalysed chemo-, regio-, and stereoselective hydrosilylation of alkenes and alkynes using a bench-stable iron(II) pre-catalyst

The chemo-, regio-, and stereoselective iron-catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41-96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron-catalysed hydrosilylation. The silane products can be oxidised to the anti-Markovnikov product of olefin hydration, and the one-pot iron-catalysed hydrosilylation-oxidation of olefins to give silane(di)ols directly is also reported. The iron pre-catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 molh-1. Initial mechanistic studies indicate an iron(I) active catalyst.