619-21-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Carboxybenzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. It plays a crucial role in the production of bicyclic cis-2-azetidinone derivatives via the Ugi 4-centre 3-component reaction, which is an important method for the synthesis of complex organic molecules with potential pharmaceutical applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-Carboxybenzaldehyde is used as a building block for the creation of more complex molecules. It is particularly useful in the synthesis of porphyrin capped with a steroidal superstructure bearing convergent hydroxy groups, which are important in various chemical and biological applications.
Used in Material Science:
3-Carboxybenzaldehyde is also used in the development of new materials, such as the synthesis of 3-[(4-amino-1,2-dihydro-1-oxo-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-6-yl)amino]methyl benzoic acid. 3-Carboxybenzaldehyde has potential applications in material science, particularly in the design and synthesis of novel materials with unique properties.

InChI:InChI=1/C8H6O3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H,(H,10,11)/p-1

Upstream product

• 626-19-7 Isophthalaldehyde 
• 36747-51-0 3-(dichloromethyl)benzoyl chloride 
• 6515-58-8 3-bromomethylbenzoic acid 
• 64407-07-4 3-(chloromethyl)benzonitrile 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 108-38-3 m-xylene 
• 124-38-9 carbon dioxide 
• 67073-72-7 3-bromobenzaldehyde dimethyl acetal 
• 64-18-6 formic acid 
• 618-51-9 3-Iodobenzoic acid 
• 31719-77-4 3-chloromethylbenzoic acid 
• 28286-79-5 3-(Hydroxymethyl)benzoic acid 
• 17789-14-9 3-(1,3-dioxolan-2-yl)-phenylbromide 

Downstream Products

• 52178-50-4 Methyl 3-formylbenzoate 
• 5006-03-1 (E)-3-(2-nitrovinyl)benzoic acid 
• 33745-47-0 3-formyl-benzoic acid ethyl ester 
• 861542-60-1 ω.ω.ω'-triethyl-m-xylylene glycol 
• 861593-25-1 3-(hydroxydiphenylmethyl)benzhydrol 
• 25974-99-6 3-(2-carboxyvinyl)benzoic acid 
• 98434-08-3 3-formyl-5-nitro-benzoic acid 
• 106456-84-2 phenacyl 3-formylbenzoate 
• 173265-29-7 tert-Butyl 3α-(3-formylbenzoyloxy)-7α-hydroxy-12α-trifluoroacetoxy-5β-cholan-24-oate 

Relevant academic research and scientific papers

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes

A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.

Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions. The reaction tolerates other functionalities for cross-coupling, such as aryl bromide, aryl chloride, aryl tosylate, and aryl pinacol boronate. The reaction proceeds through a carbonylation process with in situ generated carbon monoxide in the presence of a catalytic amount of acetic anhydride and lithium formate, avoiding the use of gaseous CO. The strategy of CO recycling in catalytic amounts is critical for the success of the reaction.

Oxidation of aromatic and aliphatic aldehydes to carboxylic acids by Geotrichum candidum aldehyde dehydrogenase

Oxidation reaction is one of the most important and indispensable organic reactions, so that green and sustainable catalysts for oxidation are necessary to be developed. Herein, biocatalytic oxidation of aldehydes was investigated, resulted in the synthesis of both aromatic and aliphatic carboxylic acids using a Geotrichum candidum aldehyde dehydrogenase (GcALDH). Moreover, selective oxidation of dialdehydes to aldehydic acids by GcALDH was also successful.

Preparation method of 3-carboxybenzaldehyde

The invention discloses a preparation method of 3-carboxybenzaldehyde. The method comprises the following steps: by using m-toluonitrile as a starting raw material, carrying out a first hydrolysis reaction, and adding an acid to carry out an acidification reaction to obtain m-toluic acid; carrying out chlorination reaction on m-toluic acid to obtain 3-carboxyl benzyl chloride; mixing the 3-carboxyl benzyl chloride and urotropin for an oxidation reaction, then adding glacial acetic acid and water for a second hydrolysis reaction to obtain the 3-carboxybenzaldehyde. According to the method disclosed by the invention, m-toluonitrile with low cost is used as a raw material, the 3-carboxybenzaldehyde is synthesized through a series of processes of hydrolysis, chlorination, oxidation and hydrolysis, and the product purity and yield are relatively high; the method has the advantages of simple and safe process operation, easily available raw materials and low cost and is suitable for industrial production.

Bisubstrate inhibitors of nicotinamide N-methyltransferase (NNMT) with enhanced activity

Nicotinamide N-methyltransferase (NNMT) catalyzes the methylation of nicotinamide to form N-methylnicotinamide. Overexpression of NNMT is associated with a variety of diseases, including a number of cancers and metabolic disorders, suggesting a role for NNMT as a potential therapeutic target. By structural modification of a lead NNMT inhibitor previously developed in our group, we prepared a diverse library of inhibitors to probe the different regions of the enzyme's active site. This investigation revealed that incorporation of a naphthalene moiety, intended to bind the hydrophobic nicotinamide binding pocket via π-πstacking interactions, significantly increases the activity of bisubstrate-like NNMT inhibitors (half-maximal inhibitory concentration 1.41 μM). These findings are further supported by isothermal titration calorimetry binding assays as well as modeling studies. The most active NNMT inhibitor identified in the present study demonstrated a dose-dependent inhibitory effect on the cell proliferation of the HSC-2 human oral cancer cell line.

Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as CO Source

A facile and practical method for the synthesis of aromatic aldehydes by palladium-catalyzed reductive carbonylation starting from aryl iodides and HCOOH is described. Compared to the known formylation procedure, HCOOH serves not only as the most convenient and environmental-friendly C1 source but also as the reviving agent in the reductive elimination process of a Pd-catalyst. Furthermore, this procedure is also applied successfully to the modification of natural products, such as vindoline, tabersonin, and vincamine, to obtain the corresponding products in good yields.

SO2F2-Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide

A one-pot Pd-catalyzed carbonylation of phenols into their corresponding aryl carboxylic acids and esters through the insertion of carbon monoxide has been developed. This procedure offers a direct synthesis of aryl carboxylic acids and esters from inexpensive and abundant starting materials (phenols, SO2F2 and CO) under mild conditions. This method tolerates a broad range of functional groups and is also applicable for the modification of complicated natural products.

IONIC LIQUID COMPOSITION

The present disclosure provides a composition for preparing aryl carboxylic acid; said composition comprising: at least one ionic liquid, at least one catalyst, at least one non-oxidizable polar solvent, and at least one oxidizable multi-alkylated arylene compound with no two successive ring positions bearing alkyl group. The present disclosure also provides a process for preparing aryl carboxylic acid.

Iron oxalate capped iron-copper nanomaterial for oxidative transformation of aldehydes

An efficient, sustainable and green procedure for the synthesis of selective orthorhombic iron(oxalate) capped Fe-Cu bimetallic oxide nanomaterial [Fe(ox)Fe-CuOx] was developed using a sodium borohydride reduction of iron(ii) salt in the presence of oxalic acid at room temperature followed by addition of copper sulfate in water. The reported method is a cost-effective chemical route for producing [Fe(ox)Fe-CuOx] nano material at the gram level with a surface area of 78.4 m2 g-1 and a pore volume of 0.141 cm3 g-1. The [Fe(ox)Fe-CuOx] nanomaterials were found to be useful as a recoverable catalyst for the oxidative transformation of an aldehyde to its corresponding ester and acid in presence of hydrogen peroxide.

Development of a Rhodium(II)-Catalyzed Chemoselective C(sp3)-H Oxygenation

We report the first example of RhII-catalyzed chemoselective double C(sp3)-H oxygenation, which can directly transform various toluene derivatives into highly valuable aromatic aldehydes with great chemoselectivity and practicality. The critical combination of catalyst Rh(OAc)2, oxidant Selectfluor, and solvents of TFA/TFAA promises the successful delivery of the oxidation with satisfactory yields. A possible mechanism involving a unique carbene-Rh complex is proposed, and has been supported by both experiments and theoretical calculations.