61266-32-8

Usage

Uses

Used in Organic Synthesis:
3-(4-NITRO-PHENYL)-PROP-2-YN-1-OL is used as a building block in organic synthesis for the preparation of various drugs and biologically active molecules, leveraging its unique structural features to facilitate the creation of complex organic compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, 3-(4-NITRO-PHENYL)-PROP-2-YN-1-OL is utilized as a key intermediate in the synthesis of new drug candidates, contributing to the discovery and development of novel therapeutic agents.
Used in Materials Science:
3-(4-NITRO-PHENYL)-PROP-2-YN-1-OL has potential applications in materials science, where its chemical properties may be harnessed to develop new materials with specific characteristics for various industrial applications.
Used as a Reagent in Chemical Reactions:
3-(4-NITRO-PHENYL)-PROP-2-YN-1-OL also serves as a reagent in chemical reactions, enabling specific transformations and processes that are essential in the synthesis of target molecules in research and development settings.

InChI:InChI=1/C9H7NO3/c11-7-1-2-8-3-5-9(6-4-8)10(12)13/h3-6,11H,7H2

Upstream product

• 107-19-7 propargyl alcohol 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 5582-62-7 1-trimethylsilyloxy-2-propyne 
• 627-09-8 Propargyl acetate 
• 61266-31-7 2-((3-(4-nitrophenyl)prop-2-yn-1-yl)oxy)tetrahydro-2H-pyran 
• 107-18-6 allyl alcohol 

Downstream Products

• 35271-56-8 3-(4-nitrophenyl)propyl-2-en-1-ol 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 61266-34-0 1-(3-bromoprop-1-yn-1-yl)-4-nitrobenzene 
• 56-75-7 chloramphenicol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 142917-86-0 (1R,2R)-2-Azido-1-(4-nitro-phenyl)-propane-1,3-diol 
• 1885-06-9 [(2R,3S)-3-(4-Nitro-phenyl)-oxiranyl]-methanol 
• 143058-48-4 [(2S,3R)-3-(4-Nitro-phenyl)-oxiranyl]-methanol 
• 1235983-71-7 diisopropyl 1-(3-(4-nitrophenyl)-2-propyn-1-yl)hydrazine-1,2-dicarboxylate 
• 1268381-64-1 1-nitro-4-(3-(3-phenylprop-2-ynylsulfonyl)prop-1-ynyl)benzene 
• 1268381-67-4 (3-(4-methoxyphenyl)prop-2-ynyl)(3-(4-nitrophenyl)prop-2-ynyl)sulfane 
• 1268381-72-1 C₁₁H₉NO₃S 
• 1268381-62-9 1-methoxy-4-(3-(3-(4-nitrophenyl)prop-2-ynylsulfonyl)prop-1-ynyl)benzene 
• 1268381-76-5 6-methoxy-4-(4-nitro-phenyl)-1,3-dihydro-naphtho[2,3-c]thiophene 2,2-dioxide 

Relevant academic research and scientific papers

Heptalene Synthesis by Addition of Aryl Acetylenes to Azulenes

Abstract: Aryl acetylenes bearing electron-withdrawing groups have been found that canadd to azulenes and yield 1,2-substituted heptalenes. Theoretical studies of thereaction mechanism helped to design the candidate molecules that have then beentested in

Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions

A bimetallic PdCu supported on amine functionalized ZIF-67 is shown to be efficient catalyst in Sonogashira-Hagihara coupling reaction of aryl iodides at room temperature and aryl bromides at 40 oC. In addition, the catalyst is used in the reduction of 4-

Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes

Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.

Rip It off: Nitro to Nitroso Reduction by Iron Half-Sandwich Complexes

Activation of [FeCl(dppe)Cp] (1) by chloride abstraction with Na[BArX4] (X = F, [B(3,5-(CF3)2-C6H3)4]; X = Cl, [B(3,5-Cl2-C6H3)4]) permits reactions with a range of nitro aromatics, RC6H4NO2 (R = halogen, Me, OMe, NO2 or NMe2), to give the cationic iron nitroso complexes [Fe{N(O)-C6H4R}(dppe)Cp][BArX4]) ([3][BArX4]). Similar reactions of 1 and Na[BArX4] with [Fe(NCC6H4NO2)(dppe)Cp][BArX4] gave bimetallic [{Fe(dppe)Cp}2{μ-NCC6H4N(O)}][BArF4]2. However, reactions of 1 and Na[BArX4] with 4-nitrophenol gave the first example of the bench-stable iron half-sandwich phenolate complex [Fe(OC6H4NO2)(dppe)Cp]+ rather than NO2 activation. The formation of complexes [3]+ likely proceeds via the unusual blue bimetallic species [{Fe(dppe)Cp}2{μ,κ2O,O′-O2NAr}]2+. This compound undergoes N-O bond cleavage, resulting in [3]+ and a FeIV=O species, which reacts via an internal C-H activation of the dppe ligand to give [FeIII(κ3O,P,P′-P(2-O-C6H4)(Ph)-C2H4-PPh2)Cp]+. Complexes [3]+ are stable under ambient conditions, are readily purified by column chromatography and can be isolated in up to 50% yield, considering that 0.5 equiv of 1 is required as the oxygen acceptor.

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.

HighlyZ-selective synthesis of 1,3-oxathiol-2-ylidenes and 4-methylene-oxazolidine-2-thionesviaatom-specific 5-exo-digcyclization of propargyl alcohol with isothiocyanate

DBU mediated 5-exo-digcyclization of isothiocyanate and propargyl alcohol leading to valuable heterocyclic compounds has been accomplished. The different modes of nucleophilicity (eitherS-selective orN-selective) of isothiocyanates were found to depend on

Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement

An unprecedented approach for efficient synthesis of functionalized allylic gem-difluorides via catalytic fluorinative Meyer–Schuster-like rearrangement is disclosed. This transformation proceeded with readily accessible propargylic fluorides, and low-cost B–F reagents and electrophilic reagents by sulfide catalysis. A series of iodinated, brominated, and trifluoromethylthiolated allylic gem-difluorides that were difficult to access by other methods were facilely produced with a wide range of functional groups. Importantly, the obtained iodinated products could be incorporated into different drugs and natural products, and could be expediently converted into many other valuable gem-difluoroalkyl molecules as well. Mechanistic studies revealed that this reaction went through a regioselective fluorination of alkynes followed by a formal 1,3-fluorine migration under the assistance of the B–F reagents to give the desired products.

Pd(0) nanoparticles immobilized on multinitrogen functionalized halloysite for promoting Sonogashira reaction: studying the role of the number of surface nitrogens in catalytic performance

Halloysite nanoclay, Hal, was amine-functionalized and subsequently reacted with 2,4,6-trichloro-1,3,5-triazine, TCT, and ethylenediamine, EDA, to provide multinitrogen containing functionality on the surface of Hal. The resulting surface-modified Hal, Ha

Pd@GO/Fe3O4/PAA/DCA: a novel magnetic heterogeneous catalyst for promoting the Sonogashira cross-coupling reaction

A hybrid system involving graphene oxide (GO), magnetic oxide (Fe3O4), acrylamide and dicyandiamide was prepared via amine functionalization of GO/Fe3O4 by means of covalent bonding with acrylamide and subsequent reaction with dicyandiamide to provide a multinitrogen containing polymer on the surface of GO. This hybrid system was utilized as a heterogeneous catalyst support for immobilizing Pd nanoparticles to provide the hybrid, Pd@GO/Fe3O4/PAA/DCA. This nano-Pd composite was characterized using Fourier transform infrared, transmission electron microscopy, scanning electron microscopy, vibrating sample magnetometer, thermogravimetric analysis, X-ray diffraction, and ICP techniques and used for promoting Sonogashira cross-coupling under mild reaction conditions. This heterogeneous and magnetic catalyst was easily separated by external magnet and was reused in a model reaction, efficiently up to six times with slight loss of catalytic activity and Pd leaching, showing the suitability of GO/Fe3O4/PAA/DCA for embedding Pd nanoparticles. To check the effect of the number of surface nitrogens of the polymeric chain on the catalytic performance, the activity of the catalyst was compared with Pd@GO/Fe3O4/PAA; increased number of the surface nitrogens on the chain polymer leads to higher loading of Pd and lower the Pd leaching.