2227-58-9

Basic information

• Product Name: 3-(4-methylphenyl)prop-2-ynoic acid
• Synonyms: 2-propynoic acid, 3-(4-methylphenyl)-
• CAS NO: 2227-58-9
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.1693
• Mol File: 2227-58-9.mol

Chemical Properties

• Boiling Point: 311.4°C at 760 mmHg
• Flash Point: 156.4°C
• Density: 1.2g/cm³
• Vapor Pressure: 0.000242mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 3-(4-methylphenyl)prop-2-ynoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methylphenyl)prop-2-ynoic acid(2227-58-9)
• EPA Substance Registry System: 3-(4-methylphenyl)prop-2-ynoic acid(2227-58-9)

Safety Data

• Hazardous Substances Data: 2227-58-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-(4-methylphenyl)prop-2-ynoic acid is utilized as a starting material in organic synthesis for the preparation of a range of pharmaceuticals and agrochemicals. Its chemical properties allow for the creation of diverse compounds with potential therapeutic and pesticidal effects.
Used in Materials Science:
In the field of materials science, 3-(4-methylphenyl)prop-2-ynoic acid is employed for its potential to contribute to the development of new materials. Its structural features make it a candidate for enhancing material properties or creating novel materials with specific characteristics.
Used in Nanotechnology:
3-(4-methylphenyl)prop-2-ynoic acid also finds applications in nanotechnology, where its unique structure and reactivity can be leveraged to synthesize nanoscale materials with distinct electronic, optical, or catalytic properties.
Used in Biological Research:
3-(4-methylphenyl)prop-2-ynoic acid has been studied for its potential biological activities, such as anti-inflammatory and anticancer properties. It is used as a subject of research to explore its effects on biological systems and its potential as a therapeutic agent.
Each of these applications takes advantage of the compound's distinctive chemical structure, which allows for a wide range of reactions and interactions in various fields.

Upstream product

• 52916-86-6 (2RS,3SR)-2,3-dibromo-3-(4-methylphenyl)propanoic acid 
• 124-38-9 carbon dioxide 
• 766-97-2 4-n-methylphenylacetylene 
• 624-31-7 4-tolyl iodide 
• 471-25-0 Propiolic acid 
• 106-38-7 para-bromotoluene 
• 86454-00-4 5-(1,2-Dibromo-2-p-tolyl-ethyl)-3-methyl-4-nitro-isoxazole 
• 56377-28-7 trans-β-Chlor-p-methylzimtsaeure-methylester 
• 91585-31-8 phenyl(p-tolylethynyl)selane 
• 96372-85-9 methyl 3-oxo-3-(p-tolyl)-2-(triphenylphosphoranylidene)propanoate 
• 16017-24-6 3-p-tolylprop-2-yn-1-ol 
• 148547-94-8 methyl 2,3-dibromo-3-p-tolylpropionic acid methyl ester 
• 7560-43-2 methyl 3-(4-methylphenyl)acrylate 
• 1866-39-3 4-methylcinnamic acid 

Downstream Products

• 7515-16-4 methyl 3-(4-methylphenyl)prop-2-ynoate 
• 52188-06-4 ethyl 3-(4-methylphenyl)prop-2-ynoate 
• 2749-93-1 1-methyl-4-(1-propyn-1-yl)benzene 
• 77930-53-1 7,10-Dimethyl-8-p-tolyl-fluoranthene 
• 77930-62-2 7,10-Dimethyl-9-p-tolyl-fluoranthene-8-carboxylic acid 
• 77930-54-2 7,10-Diethyl-8-p-tolyl-fluoranthene 
• 77930-63-3 7,10-Diethyl-9-p-tolyl-fluoranthene-8-carboxylic acid 
• 77930-55-3 7,10-Dipropyl-8-p-tolyl-fluoranthene 
• 77945-43-8 7,10-Dipropyl-9-p-tolyl-fluoranthene-8-carboxylic acid 
• 77930-56-4 7,10-Dibutyl-8-p-tolyl-fluoranthene 
• 77930-64-4 7,10-Dibutyl-9-p-tolyl-fluoranthene-8-carboxylic acid 
• 62849-00-7 p-Tolyl-propynoyl chloride 
• 33491-05-3 1-(2-bromoethynyl)-4-methylbenzene 
• 33675-56-8 1-(iodoethynyl)-4-methylbenzene 

Relevant articles and documents

Porous Carbon Nitride Frameworks Derived from Covalent Triazine Framework Anchored Ag Nanoparticles for Catalytic CO2 Conversion

Porous carbon nitride frameworks (PCNFs) with uniform and rich nitrogen dopants and abundant porosity were successfully fabricated through the direct carbonization of the covalent triazine frameworks (CTFs) at different pyrolysis temperatures and used as supports to anchor and stabilize Ag nanoparticles (NPs) for catalytic CO2 conversion. Importantly, the pyrolysis temperature plays a crucial role in the properties of porous carbon nitride frameworks. The material carbonized at 700 °C showed the highest surface area and micro- and mesoporous structure with a certain interlayer distance. Taking advantage of their unique surface characteristics, PCNF-supported Ag NP catalysts (Ag/PCNF-T, T=pyrolysis temperature) were prepared by a simple chemical method. A series of characterizations revealed that Ag NPs are embedded in the porous carbon nitride frameworks and confined to a relatively small size with high dispersion owing to the assistance of the abundant surface groups and porous structures. The as-obtained Ag/PCNF-T catalysts, especially Ag/PCNF-700, showed excellent catalytic activity, selectivity, and stability for the carboxylation of CO2 with terminal alkynes under mild conditions. This can be due to the existence of abundant nitrogen atoms and diverse porosity, which resulted in highly efficient catalytic activity and stability.

Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter

A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.

Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions

A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).

Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues

A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw

Pre-carbonized nitrogen-rich polytriazines for the controlled growth of silver nanoparticles: Catalysts for enhanced CO2chemical conversion at atmospheric pressure

High catalytic activity and sufficient durability are two unavoidable key indices of an efficient heterogeneous catalyst for the direct carboxylation of terminal alkynes with CO2 conversion. Nitrogen-rich covalent triazine frameworks (CTFs) are promising substrates, while random distribution of some residual -NH2 groups brings challenges to the controlled growth of catalytic species. Here, we adopt a pre-carbonization protocol, annealing below the carbonization temperature, to eliminate the random -NH2 groups in CTFs and meanwhile to promote polycondensation degree under the premise of maintaining the pore structure. Benefiting from the improved condensation and orderly N atoms, p-CTF-250, for which CTFs are annealed at 250 °C, exhibits improved CO2 adsorption capacity and the ability to control the growth of Ag NPs. Mono-dispersed Ag NPs are generated controllably and entrapped to form Ag@p-CTF-250 catalysts. These Ag@p-CTF-250 catalysts were employed in the direct carboxylation of various terminal alkynes with CO2 under mild conditions (50 °C, 1 atm) and showed excellent catalytic activity. In addition, these catalysts have robust recyclability and can be used for at least 5 catalytic runs while retaining yield above 90%. CO2 conversion proceeds well under the synergistic effect between the high CO2 capture capability and the uniform tiny Ag NPs in Ag@p-CTF-250 "nanoreactors". The results represent an efficient strategy for controlling the growth of metallic nanoparticles in porous organic polymer substrates containing disordered heteroatoms.

Method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide

The invention belongs to the field of organic synthesis, and particularly relates to a method for synthesizing acetylenic acid by using terminal alkyne and carbon dioxide. The method comprises the experimental steps that alkyne, alkali and a solvent are added into a reaction tube, the alkyne serves as a raw material, the alkali and the solvent provide a strong alkaline environment, CO2 is introduced into a reaction container to form a carbon dioxide atmosphere, heating and stirring reaction are carried out, after the reaction is finished, cooling is carried out to the room temperature, extraction and liquid separation are carried out, a water layer is acidified, then separation and purification are further carried out, and the acetylenic acid compound is obtained. The method is carried out under the conditions of low temperature and normal pressure, does not need to add a metal catalyst, is single in product and convenient to separate, good in substrate applicability and safe and simple to operate, and has potential industrial application prospects and good economic benefits.

N-Heterocyclic carbene-nitrogen molybdenum catalysts for utilization of CO2

Three new N-heterocyclic carbene-nitrogen molybdenum complex was synthesized, and its catalytic activity was evaluated in the cycloaddition of epoxides with CO2. The molybdenum complex combined with tetrabutyl ammonium iodide (TBAI) resulted in a catalytic system for efficient conversion of a wide range of terminal and internal epoxides under 80 °C and 5–7 bar pressure for CO2. The cooperative catalysis mechanism between molybdenum complex and TBAI was elucidated, in which molybdenum complex was used as Lewis acid, and TBAI was employed as nucleophilic reagent. In addition, the NHC-Mo catalytic system was also successfully applied for the direct carboxylation of terminal alkynes with CO2.

An efficient Ag/MIL-100(Fe) catalyst for photothermal conversion of CO2 at ambient temperature

The conversion of CO2 under mild condition is of great importance because these reactions involving CO2 can not only produce value-added chemicals from abundant and inexpensive CO2 feedstock but also close the carbon cycle. However, the chemical inertness of CO2 requires the development of high-performance catalysts. Herein, Ag nanoparticles/MIL-100(Fe) composites were synthesized by simple impregnation-reduction method and employed as catalysts for the photothermal carboxylation of terminal alkynes with CO2. MIL-100(Fe) could stabilize Ag nanoparticles and prevent them from aggregation during catalytic process. Taking the advantages of photothermal effects and catalytic activities of both Ag nanoparticles and MIL-100(Fe), various aromatic alkynes could be converted to corresponding carboxylic acid products (86%–92% yields) with 1 atm CO2 at room temperature under visible light irradiation when using Ag nanoparticles/MIL-100(Fe) as photothermal catalysts. The catalysts also showed good recyclability with almost no loss of catalytic activity for three consecutive runs. More importantly, the catalytic performance of Ag nanoparticles/MIL-100(Fe) under visible light irradiation at room temperature was comparable to that upon heating, showing that the light source could replace conventional heating method to drive the reaction. This work provided a promising strategy of utilizing solar energy for achieving efficient CO2 conversion to value-added chemicals under mild condition.

Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes

An organocatalytic strategy for the direct carboxylation of terminal alkynes with CO2 has been developed. The combined use of a bifunctional organocatalyst and Cs2CO3 resulted in a robust catalytic system for the preparation of a range of propiolic acid derivatives in high yields with broad substrate scope using CO2 at atmospheric pressure under mild temperatures (60 °C). This work has demonstrated that this organocatalytic method offers a competitive alternative to metal catalysis for the carboxylation of terminal alkynes and CO2. In addition, this protocol was suitable for the three-component carboxylation of terminal alkynes, alkyl halides, and CO2.

Microwave-assisted fabrication of a mixed-ligand [Cu4(μ3-OH)2]-cluster-based metal–organic framework with coordinatively unsaturated metal sites for carboxylation of terminal alkynes with carbon dioxide

The development of efficient and stable metal–organic framework (MOF) catalysts with coordinatively unsaturated metal sites for modern organic synthesis is greatly important. Herein, a robust [Cu4(μ3-OH)2]-cluster-based MOF (Cu-MOF) with a mixed-ligand system was successfully fabricated by a microwave-assisted method under mild conditions. The as-prepared Cu-MOF catalyst possessing unsaturated Cu (II) sites exhibited excellent catalytic activity toward the direct carboxylation of 1-ethynylbenzene with CO2, and various propiolic acid derivatives were synthesized in moderate to good yields under optimized reaction conditions. Furthermore, the catalyst remained stable and could be easily recycled for five sequential runs without incredible decrease in catalytic efficiency.