61266-36-2

Usage

Uses

Used in Organic Synthesis:
4-(3-Hydroxy-prop-1-ynyl)-benzoic acid methyl ester is used as a building block in organic synthesis for the creation of various biologically active molecules. Its versatile chemical properties allow it to be a key component in the synthesis of complex organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(3-Hydroxy-prop-1-ynyl)-benzoic acid methyl ester serves as an important intermediate. It is utilized in the development and production of pharmaceuticals due to its potential to form biologically active molecules, contributing to the discovery of new drugs and therapeutic agents.
Used in Agrochemicals:
4-(3-Hydroxy-prop-1-ynyl)-benzoic acid methyl ester is also used in the agrochemical sector, where it plays a role in the synthesis of compounds that have applications in agriculture, such as pesticides and herbicides, enhancing crop protection and yield.
Used in Materials Science:
In the field of materials science, 4-(3-Hydroxy-prop-1-ynyl)-benzoic acid methyl ester has potential applications in the synthesis of advanced materials and polymers. Its unique structure allows for the development of new materials with specific properties for various industrial applications.

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 107-18-6 allyl alcohol 
• 619-44-3 methyl 4-iodobenzoate 
• 107-19-7 propargyl alcohol 
• 19070-80-5 n-<(trimethylsiloxy)methyl>phthalimide 
• 75867-41-3 4-trimethylsilanylethynyl-benzoic acid methyl ester 
• 586-76-5 4-Bromobenzoic acid 
• 50-00-0 formaldehyd 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 7681-65-4 copper(I) iodide 

Downstream Products

• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 15403-22-2 4-(3-hydroxy-propyl)-benzoic acid methyl ester 
• 1146969-05-2 diethyl 5-formyl-4-(4-(methoxycarbonyl)phenyl)furan-2,3-dicarboxylate 
• 1241859-86-8 diethyl 4-[4-(methoxycarbonyl)phenyl]-5-methylfuran-2,3-dicarboxylate 
• 58810-87-0 4-(3-Hydroxy propyl)benzoic acid 
• 61266-35-1 1-bromo-3-(p-methoxycarbonylphenyl)prop-2-yne 

Relevant academic research and scientific papers

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.

Compound as protein degradation agent and preparation method and medical application thereof

The invention discloses a compound serving as a protein degrading agent and a preparation method and medical application thereof, and particularly discloses a compound represented by the formula (I) and a pharmaceutically acceptable salt thereof, and the

Mimics of Pincer Ligands: An Accessible Phosphine-Free N-(Pyrimidin-2-yl)-1,2-azole-3-carboxamide Framework for Binuclear Pd(II) Complexes and High-Turnover Catalysis in Water

We report for the first time cyclic phosphine-free "head to tail"N,N,N pincer-like (pincer complexes mimicking) N-(pyrimidin-2-yl)-1,2-azole-3-carboxamide Pd(II) complexes with deprotonated amide groups as high-turnover catalysts (TON up to 106, TOF up to 1.2 × 107 h-1) for cross-coupling reactions on the background of up to quantitative yields under Green Chemistry conditions. The potency of the described catalyst family representatives was demonstrated in Suzuki-Miyaura, Mizoroki-Heck, and Sonogashira reactions on industrially practical examples. Corresponding ligands could be synthesized based on readily available reagents through simple chemical transformations. Within the complex structures, a highly unusual 1,3,5,7-tetraza-2,6-dipalladocane frame could be observed.

Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents

An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).

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.

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.

Catalytic claisen rearrangement by intercepting ketenimines with propargylic alcohols: A strategy to generate and transform ketenimines from radicals

An efficient strategy for facilitating the cross-coupling of two radicals has been established via the coordination of a radical with a metal catalyst. This strategy provides a remarkable ability to harness the reactivity of nitrile-containing azoalkanes and enables a novel cascade reaction with nitrile-containing azoalkanes and propargylic alcohols to be established. By using this reaction, a range of acetylenic and allenic amides were obtained that provides a versatile platform for further derivatizations.

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

Metal-free aminothiation of alkynes: Three-component tandem annulation toward indolizine thiones from 2-alkylpyridines, ynals, and elemental sulfur

A metal-free three-component annulation reaction for the synthesis of indolizine thiones via tandem C-C/C-N/C-S bond formation was developed. Various 2-alkylpyridines with aromatic ynals and elemental sulfur proceeded smoothly under catalyst-free conditions, and the desired products were obtained in moderate to excellent yields.

Palladium-Catalyzed Nitrile-Assisted C(sp3)-Cl Bond Formation for Synthesis of Dichlorides

A palladium-catalyzed coupling procedure of alkenes with alkynylnitriles has been demonstrated for the synthesis of dichlorides. The reaction is the first example of nitrile-assisted C(sp3)-Cl formation promoted by coordination of a cyano group with an alkylpalladium(II) complex. The construction of a five-membered cycle intermediate successfully inhibits the β-hydride abstraction, resulting in direct C-Cl bond reductive elimination of alkylpalladium(II) chloride.