19955-99-8

Usage

Uses

Used in Chemical Synthesis:
3-VINYLBENZALDEHYDE is used as a key intermediate for the synthesis of various complex organic molecules. Its presence in the molecular structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in Pharmaceutical Industry:
3-VINYLBENZALDEHYDE is used as a starting material for the preparation of pharmaceutical compounds, such as 2-(3-vinylphenyl)-1,3-dioxolane. This application takes advantage of its reactive vinyl group and aromatic ring, which can be further modified to create bioactive molecules with potential therapeutic properties.
Used in Material Science:
3-VINYLBENZALDEHYDE is used as a monomer for the synthesis of polymers, such as poly(3-vinylbenzaldehyde-co-dimethylacrylamide) (PVBA-co-PDMA) copolymers. These copolymers can exhibit unique properties, such as enhanced solubility, stability, or reactivity, which can be tailored for specific applications in material science.
Used in the Synthesis of Imines:
3-VINYLBENZALDEHYDE is used as a precursor for the preparation of various substituted imines. Imines are important intermediates in organic synthesis and can be used to construct a wide range of organic compounds, including pharmaceuticals, agrochemicals, and natural products.
Used in the Synthesis of Monomers with Specific Moieties:
3-VINYLBENZALDEHYDE is used as a building block for the synthesis of monomers bearing a 2,4,5-triphenylimidazole moiety. These monomers can be polymerized to form polymers with specific properties, such as enhanced thermal stability, electrical conductivity, or optical characteristics, which can be applied in various industries, including electronics, sensors, and energy storage.

InChI:InChI=1/C9H8O/c1-2-8-4-3-5-9(6-8)7-10/h2-7H,1H2

Upstream product

• 626-19-7 Isophthalaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 3132-99-8 m-bromobenzoic aldehyde 
• 74-85-1 ethene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 108-57-6 1,3-divinylbenzene 
• 75927-49-0 pinacol vinylboronate 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 77123-56-9 3-ethynylbenzaldehyde 
• 141-82-2 malonic acid 

Downstream Products

• 115104-31-9 2-(3-ethenylphenyl)-1,3-dioxolane 
• 1026688-27-6 cyclopropanecarboxylic acid {3-[2-(3-formyl-phenyl)-vinyl]-phenyl}-(8-methoxy-2,2-dimethyl-2H-chromen-7-ylmethyl)-amide 
• 1115020-88-6 3-(3-formylphenyl)-1-triisopropylsilylbut-1-yne 
• 1206831-82-4 1-(3-butyrylphenyl)pentan-3-one 
• 342411-74-9 C₁₂H₁₆O 
• 1206831-84-6 C₁₂H₁₄O 
• 1197335-38-8 methyl (2S,5E)-2-(tritylamino)-4-oxo-6-(3-ethenylphenyl)hex-5-enoate 
• 1228957-93-4 C₂₇H₁₉Cl₂N₃O₃ 
• 1228078-87-2 C₂₂H₂₁N₃O₄ 
• 1221442-04-1 3-((1E,3Z)-3,4-diphenylbuta-1,3-dienyl)benzaldehyde 
• 1290610-44-4 N-phenyl-3-vinylbenzohydrazonoyl chloride 
• 1290610-46-6 N-(4-bromophenyl)-3-vinylbenzohydrazonoyl chloride 
• 1290610-48-8 N,N'-diphenyl-3-vinylbenzohydrazonamide 
• 1290610-50-2 N'-(4-bromophenyl)-N-phenyl-3-vinylbenzohydrazonamide 

Relevant academic research and scientific papers

Copper-Catalyzed Asymmetric Radical 1,2-Carboalkynylation of Alkenes with Alkyl Halides and Terminal Alkynes

A copper-catalyzed intermolecular three-component asymmetric radical 1,2-carboalkynylation of alkenes has been developed, providing straightforward access to diverse chiral alkynes from readily available alkyl halides and terminal alkynes. The utilization of a cinchona alkaloid-derived multidentate N,N,P-ligand is crucial for the efficient radical generation from mildly oxidative precursors by copper and the effective inhibition of the undesired Glaser coupling side reaction. The substrate scope is broad, covering (hetero)aryl-, alkynyl-, and aminocarbonyl-substituted alkenes, (hetero)aryl and alkyl as well as silyl alkynes, and tertiary to primary alkyl radical precursors with excellent functional group compatibility. Facile transformations of the obtained chiral alkynes have also been demonstrated, highlighting the excellent complementarity of this protocol to direct 1,2-dicarbofunctionalization reactions with C(sp2/sp3)-based reagents.

Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes

The copper(II)-promoted free-radical oxidative difunctionalization of terminal alkenes to access ketoazides by utilizing molecular oxygen has been reported. A series of styrene derivatives have been evaluated and were found to be compatible to give the desired difunctionalized products in moderate to good yields. The role of molecular oxygen both as an oxidant and oxygen atom source in this catalytic transformation has been unquestionably demonstrated by 18O-labeling studies and a radical mechanistic pathway involving the oxidative formation of azidyl radicals is also designed. This environment-friendly catalytic oxidative protocol can transform aldehyde to nitrile.

VINYL COMPOUNDS AS FGFR AND VEGFR INHIBITORS

FGFR and VEGFR inhibitors are provided, and compounds represented by formula (1) or formula (II) as FGFR and VEGFR inhibitors, pharmaceutically acceptable salts or tautomers thereof are specifically disclosed.

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE

The invention relates to a compound of Formula (I), or pharmaceutically acceptable enantiomers, or salts thereof. The present invention also relates to the use of compounds of Formula (I) as selective inhibitors of indoleamine 2,3-dioxygenase. The inventi

Oxidative trifluoromethylation and fluoroolefination of unactivated olefins

Fluorine-containing organic compounds are gaining increasing importance in medicinal chemistry. Described herein is a mild and efficient method for the radical addition of olefins with TMSCF3 and TMSCF2R (R = COOEt or CF3) to deliver various α-trifluoromethylated ketones and α-fluoroolefinated ketones.

Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow

Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.

Facile regio- and stereoselective hydrometalation of alkynes with a combination of carboxylic acids and group 10 transition metal complexes: Selective hydrogenation of alkynes with formic acid

A facile, highly stereo- and regioselective hydrometalation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid, and a zerovalent group 10 transition metal complex M(PEt3)4 (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometalation does not proceed via the reaction of alkyne with a hydridometal generated by the protonation of a carboxylic acid with Pt(PEt 3)4, but proceeds via a reaction of an alkyne coordinate metal complex with the acid. This finding clarifies the long proposed reaction mechanism that operates via the generation of an alkenylpalladium intermediate and subsequent transformation of this complex in a variety of reactions catalyzed by a combination of Bronsted acid and Pd(0) complex. This finding also leads to the disclosure of an unprecedented reduction of alkynes with formic acid that can selectively produce cis-, trans-alkenes and alkanes by slightly tuning the conditions.

Ferromagnetic spin-delocalized electron donors for multifunctional materials: π-conjugated benzotriazinyl radicals

We have developed new synthetic methodology for benzotriazinyl radicals that exhibit spin delocalization, low oxidation potentials, and ferromagnetic interactions in the solid state via π-π interactions, making them promising candidates for multifunctiona

Polymeric nitrons. 2. Synthesis, irradiation and waveguide mode spectroscopy of polymeric nitrons derived from polymeric benzaldehydes and N-isopropylhydroxylamine

Various vinylbenzaldehydes were prepared using the Heck reaction: 4-vinylbenzaldehyde (14), 3-vinylbenzaldehyde (15), 2-vinylbenzaldehyde (18a), 2-hydroxy-4-vinylbenzaldehyde (16) and 4-[(4-vinylbenzyl)oxy]benzaldehyde (6). The four monomers (6, 14, 15, 16) were polymerized using AIBN as initiator at 70 °C for 24 h to yield the corresponding homopolymers (7, 19, 23, 25) and a copolymer (20) with styrene. The molecular weights are about 10 000. The polymer analogous condensation of the aldehyde groups with an excess of N-isopropylhydroxylamine (8) at room temperature produces polymeric nitrons (9, 21, 22, 24, 26) in almost quantitative yields. All nitron functions were irradiated, and the intramolecular cyclization of the nitrons to the corresponding oxaziridines was examined. Waveguide mode spectroscopy of poly(4-vinylbenzaldehyde-N-isopropylnitron) (21) shows that the changes in film thickness are low but the changes in refractive indices are significant after irradiation. Oxaziridine 10 has high thermal stability with respect to ring opening. No structural change was detected after irradiation of the hydrexyphenyl-modified polynitron (26). A low molecular weight model compound (2-hydroxybenzaldehyde-N-methylnitron, 28) was prepared id order to examine this abnormal photochemical behavior and also showed that it is highly resistant to UV irradiation.

Development of a novel series of styrylquinoline compounds as high- affinity leukotriene D4 receptor antagonists: Synthetic and structure- activity studies leading to the discovery of (±)-3-[[[3-[2-(7-chloro-2- quinolinyl)-(E)-ethenyl]phenyl][[3-(dimethylamino)-3- oxopropyl]thio]methyl]thio]propionic acid

Based on LTD4 receptor antagonist activity of 3-(2-quinolinyl-(E)- ethenyl)pyridine (2) found in broad screening, structure-activity studies were carried out which led to the identification of 3-[[[3-[2-(7-chloro-2- quinolinyl)-(E)-ethenyl]phenyl][[3-(dimethylamino)-3- oxopropyl]thio]methyl]thio]propionic acid (1, MK-571) as a potent and orally active LTD4 receptor antagonist. These studies demonstrated that a phenyl ring could replace the pyridine in 2 without loss of activity, that 7-halogen substitution in the quinoline group was optimal for binding, that the (E)- ethenyl linkage was optimal, that binding was enhanced by incorporation of a polar acidic group or groups in the 3-position of the aryl ring, and that two acidic groups could be incorporated via a dithioacetal formed from thiopropionic acid and the corresponding styrylquinoline 3-aldehyde to yield compounds such as 20 (IC50 = 3 nM vs [3H]LTD4 binding to the guinea pig lung membrane). It was found that one of the acidic groups could be transformed into a variety of the amides without loss of potency and that the dimethylamide 1 embodied the optimal properties of intrinsic potency (IC50 = 0.8 nM on guinea pig lung LTD4 receptor) and oral in vivo potency in the guinea pig, hyperreactive rat, and squirrel monkey. The evolution of 2 to 1 involves the increase of >6000-fold in competition for [3H]LTD4 binding to guinea pig lung membrane and a >40-fold increase in oral activity as measured by inhibition of antigen-induced dyspnea in hyperreactive rats.