1877-72-1

Usage

Uses

Used in Coordination Polymer Synthesis:
3-Cyanobenzoic acid is used as a ligand in the preparation of coordination polymers, specifically in the synthesis of Co(II)-doped Zn(II)-tetrazole-benzoate coordination polymers. It plays a crucial role in the in situ [2+3] cycloaddition reactions with NaN3 in the presence of Zn(II) and/or Co(II) salts under hydrothermal conditions, leading to the formation of these polymers with potential applications in various fields.
Used in the Synthesis of Three-Dimensional Coordination Polymers:
In the field of coordination polymer chemistry, 3-cyanobenzoic acid is utilized as a starting material for the synthesis of three-dimensional coordination polymers, such as [Mn3(OH)2Na2(3-cnba)6]n. This particular polymer is formed through the reaction involving 3-Hcnba (3-cyanobenzoic acid) and demonstrates the versatility of 3-CNBA in constructing complex and functional coordination polymer structures.
These applications highlight the significance of 3-cyanobenzoic acid as a key component in the development of new materials with potential applications in areas such as catalysis, gas storage, and magnetic materials, among others. Its chemical properties and ability to form stable coordination polymers make it a promising candidate for further research and development in material science.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 2589, 1988 DOI: 10.1016/S0040-4039(00)86119-5

InChI:InChI=1/C8H5NO2/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4H,(H,10,11)/p-1

Upstream product

• 121-91-5 isophthalic acid 
• 151-50-8 potassium cyanide 
• 99-05-8 meta-aminobenzoic acid 
• 75-44-5 phosgene 
• 100-47-0 benzonitrile 
• 620-22-4 3-Methylbenzonitrile 
• 24964-64-5 3-Cyanobenzaldehyde 
• 83112-50-9 α-hydroxy-3-cyanoacetophenone 
• 67-56-1 methanol 
• 6952-59-6 3-cyanobromobenzene 
• 201230-82-2 carbon monoxide 
• 626-17-5 benzene-1,3-dicarbonitrile 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 

Downstream Products

• 24964-64-5 3-Cyanobenzaldehyde 
• 13531-48-1 methyl 3-cyanobenzoate 
• 120803-00-1 3-{2-[3-Methyl-3H-thiazol-(2E)-ylidene]-acetyl}-benzonitrile 
• 156266-09-0 C₆₀H₇₈N₂O₁₄Si₂ 
• 131236-57-2 lithium 3-cyanobenzene-1-carboxylate 
• 77976-07-9 3-cyanobenzoyl fluoride 
• 1055030-85-7 C₆₀H₇₈N₂O₁₄Si₂ 
• 52820-49-2 3-Amidinium benzoate 
• 6136-62-5 3-benzoylbenzonitrile 
• 410527-84-3 3-cyanobenzoyl-D-tryptophan methyl ester 
• 108618-96-8 N-benzyl-3-cyanobenzamide 
• 208836-54-8 benzyl 3-cyanobenzoate 
• 942199-41-9 N-(carbamoyl-diphenyl-methyl)-3-cyano-benzamide 
• 101861-45-4 3-cyano-benzoyl azide 

Relevant academic research and scientific papers

Stepwise benzylic oxygenation via uranyl-photocatalysis

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst

A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.

Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?

While polystyrene is widely used in daily life as a synthetic plastic, the subsequently selective degradation is still very challenging and highly required. Herein, we disclose a highly practical and selective reaction for the catalytically efficient oxidation of alkyl aromatics (including 1°, 2°, and 3° alkyl aromatics) to carboxylic acids. While dioxygen was used as the sole terminal oxidant, this protocol was catalyzed by the inexpensive and readily available ferric compound (FeCl3) with irradiation of visible light (blue LEDs) under only 1 atmosphere of O2 at room temperature. This system could further facilitate the selective degradation of polystyrene to benzoic acid, providing an important and practical tool to generate high-value chemical from abundant polystyrene wastes.

Cobalt-Catalyzed Deprotection of Allyl Carboxylic Esters Induced by Hydrogen Atom Transfer

A brief, efficient method has been developed for the removal of the allyl protecting group from allyl carboxylic esters using a Co(II)/TBHP/(Me2SiH)2O catalytic system. This facile strategy displays excellent chemoselectivity, functional group tolerance, and high yields. This transformation probably occurs through the hydrogen atom transfer process, and a Co(III)-six-membered cyclic intermediate is recommended.

Cleavage of Carboxylic Esters by Aluminum and Iodine

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**

The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids

A mild and metal-free procedure is reported for the aerobic oxidation of substituted toluenes to carboxylic acids by using CBr 4 as initiator under irradiation from a 400 nm blue light-emitting diode.

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

Synthesis method of benzoic acid compounds

The invention discloses a photocatalytic oxidation synthesis method of benzoic acid compounds, and the photocatalytic oxidation synthesis method comprises the following specific steps: mixing and dissolving toluene compounds and a catalyst in a solvent, reacting for 24-60h in the presence of an oxidant under the conditions of 350-460 nm LED illumination and a temperature of 20-80 DEG C, and performing post-treatment on the reaction liquid to obtain the benzoic acid compounds. The photocatalytic oxidation synthesis method has the advantages of no need of metal catalysts, simple operation and mild reaction conditions; oxygen is used as an oxidant, and the photocatalytic oxidation synthesis method has high atom economy, cheap reagent and environmental protection. The photocatalytic oxidationsynthesis method has good substrate applicability, and various substituents can realize the synthesis of corresponding benzoic acid compounds.

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.