1846-70-4

Usage

Uses

Used in Fragrance and Flavor Industry:
2-Nonynoic acid is used as a key ingredient for creating unique scents and flavors, contributing to the development of novel fragrances and taste profiles in consumer products.
Used in Pharmaceutical Synthesis:
2-Nonynoic acid serves as an intermediate in the synthesis of various pharmaceuticals, playing a crucial role in the production of medications that address a range of health concerns.
Used in Pesticide and Insect Repellent Manufacturing:
2-Nonynoic acid is utilized as an intermediate in the manufacturing of pesticides and insect repellents, helping to develop effective solutions for pest control and protection against insect-borne diseases.
Used in Polymer Science:
2-Nonynoic acid has potential applications in the field of polymer science, where it is used as a precursor to various organic compounds, contributing to the advancement of polymer materials with specific properties and applications.
Overall, 2-Nonynoic acid is a significant component in a wide range of industrial processes and applications, from enhancing consumer products to contributing to scientific research and development.

InChI:InChI=1/C9H14O2/c1-2-3-4-5-6-7-8-9(10)11/h2-6H2,1H3,(H,10,11)

Upstream product

• 629-05-0 n-octyne 
• 124-38-9 carbon dioxide 
• 55988-36-8 1,3-dilithio-oct-1-yne 
• 113138-67-3 1-methoxy-2-nonynyl phenyl sulfide 
• 153940-39-7 (1-Chloro-non-2-ynylsulfanyl)-benzene 
• 541-41-3 chloroformic acid ethyl ester 
• 111-80-8 methyl non-2-ynoate 
• 15719-55-8 trimethyl(oct-1-yn-1-yl)silane 
• 6482-39-9 sodium methyl carbonate 
• 133188-94-0 Non-2-ynylsulfanyl-benzene 

Downstream Products

• 111-80-8 methyl non-2-ynoate 
• 10031-92-2 ethyl non-2-ynoate 
• 201009-33-8 Non-2-ynoic acid pentafluorophenyl ester 
• 16630-91-4 2-methylheptanal 
• 1577-98-6 (E)-2-nonenoic acid 
• 14895-21-7 3-benzoyl-4-hydroxy-6-phenyl-2H-pyran-2-one 
• 144493-14-1 1-methoxy-4-(oct-1-ynyl)benzene 
• 1610944-19-8 (E)-3-(dimethyl(phenyl)silyl)non-2-enoic acid 
• 1610944-21-2 ethyl (E)-(3-(dimethyl(phenyl)silyl)non-2-enoyl)-L-leucinate 
• 1610944-18-7 (S,E)-3-(3-(dimethylphenyl)silylnon-2-enoyl)-4-isopropyloxazolidin-2-one 
• 1610944-33-6 (S,Z)-3-(3-(dimethylphenyl)silylnon-2-enoyl)-4-isopropyloxazolidin-2-one 
• 1360613-30-4 4-cyclohexyl-5-heptylidene-3-pentyloxazolidin-2-one 
• 64576-90-5 trans,trans-2,4-nonadienol 
• 629-05-0 n-octyne 

Relevant academic research and scientific papers

Core-shell metal-organic frameworks and metal functionalization to access highest efficiency in catalytic carboxylation

A core-shell metal-organic frameworks (MOF@MOF) based on the Zr-MOFs assembly from core-structure UiO-66 combined with shell-structure UiO-67-BPY were explored. The synthesized materials were characterized via XRD, FTIR, SEM, TEM, and surface area analysis, etc. indicating the presence of a core-shell structure of UiO-66@UiO-67-BPY. Furthermore, incorporation of the bipyridinic (BPY) group in the linker used to construct the shell layer (UiO-67-BPY) could coordinate with active metal species and thus create an advantage for site-selective metal incorporation in the core-shell structure. Silver (Ag) was selected for the selective metal incorporation and an excellent Ag-dispersion via coordination with the bipyridinic groups in the UiO-67-BPY layer of the core-shell material was obtained. The synthesized material (UiO-66@UiO-67-BPY-Ag) was successfully applied as a heterogeneous catalyst for the CO2 fixation via carboxylation of terminal alkynes. The catalytic material showed excellent yields using at a low Ag-loading under mild reaction condition (50 °C, 1 bar). Moreover, the catalyst can be recycled for at least 5 times maintaining a stable catalytic performance. Interestingly, the high catalytic activity of the synthesized material demonstrated clearly the beneficial advantage of the metalated core-shell structure over the reported routes to synthesize silver catalysts such as encapsulated Ag nanoparticles (AgNP@MOF) or Ag-bidentately coordinated on traditional MOFs applying the same reaction model.

DBU and copper(I) mediated carboxylation of terminal alkynes using supercritical CO2 as a reactant and solvent

An organic solvent free, DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene)-mediated and copper(I)-catalyzed CH activating carboxylation of terminal alkynes in supercritical CO2 (ScCO2) was developed in this work. Terminal alkynes react with ScCO2 in the presence of CuI/DBU and produce the corresponding functionalized propiolic acids in excellent yields. Under the optimized conditions, carbon dioxide can act as both reactant and solvent for the reaction. DBU serves as a ligand of copper catalyst, nucleophile, and base during the reaction. DBU alone can also mediate the direct CH carboxylation in the absence of transit metal catalyst. But the reaction requires a higher reaction temperature and pressure to obtain desired yields.

Gold-catalyzed homo- And cross-annulation of alkynyl carboxylic acids: a facile access to substituted 4-hydroxy 2: H -pyrones and total synthesis of pseudopyronine A

A Au(i)-catalyzed homo- and cross-annulation reaction of alkynyl carboxylic acids offering 3,6-disubstituted 4-hydroxy 2H-pyrones has been demonstrated. The reaction tolerates various substituted alkynyl carboxylic acids and moderate to good yields of α-pyrone scaffolds have been observed. Later, a gram-scale reaction of the acid and the total synthesis of the natural product pseudopyronine A have been carried out successfully.

Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones

Reported is the synthesis of carboxylic acids, symmetrical ketones, and unsymmetrical ketones with selectivity achieved by exploiting the differential reactivity of sodium methyl carbonate with Grignard and organolithium reagents.

Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents

A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.

Cobalt(III)-Catalyzed Construction of Benzofurans, Benzofuranones and One-Pot Orthogonal C?H Functionalizations to Access Polysubstituted Benzofurans

Benzofuran and benzofuranone derivatives have been synthesized through exclusive 5-exo-dig intramolecular hydroarylation using the amide-directed, cost-effective, high-valent Cp*CoIII-catalytic system. Challenging one-pot, orthogonal C?H functionalizations using two different electrophiles are also reported to afford polysubstituted benzofurans. Several valuable functional group interconversions along with removal of the amide directing group provide a route to access several diversely functionalized benzofurans. The mechanistic study suggests a reversible cobaltation step is operative here. (Figure presented.).

Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System

A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.

Carboxylation of terminal alkynes with CO2 using novel silver N-heterocyclic carbene complexes

Four novel N-heterocyclic carbene (NHC) silver complexes, I-IV, have been synthesized and characterized. The single X-ray crystal diffraction data indicate a dinuclear solid-state structure for I and III and a mononuclear structure for II and IV. These complexes have been successfully used as efficient catalysts for the C-H activating carboxylation of terminal alkynes with CO2. A wide range of substrates with various functional groups afforded the corresponding aryl or alkyl substituted propiolic acids in good yields under mild conditions. Moreover, the role of bases and the reaction mechanism is thoroughly discussed.

Copper-Catalyzed Domino Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones using Cyanamide as a Building Block

An efficient and practical copper-catalyzed domino synthesis of benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones has been developed. The protocol uses N-(2-halophenyl)-3-alkylpropiolamides and cyanamide as the starting materials, inexpensive copper(I) iodide and pipecolinic acid as the catalyst and ligand, and the corresponding products were obtained in moderate to good yields.

PROCESS FOR PREPARING A PROPIOLIC ACID OR A DERIVATIVE THEREOF

The invention relates to a process for preparing a propiolic acid or a derivative thereof by reacting a terminal alkyne with carbon dioxide, which comprises performing the reaction in the presence of a base and a copper complex, especially a copper (I) complex having at least one ligand, at least one of the ligands of the copper complex being selected from monodentate ligands which have an aminic or iminic nitrogen atom capable of coordination with copper, and polydentate ligands having at least two atoms or atom groups which are capable of simultaneous coordination with copper and are selected from nitrogen, oxygen, sulfur, phosphorus and carbene carbon.