Benzene-1,3,5-tricarboxaldehyde

• CAS: 3163-76-6
• Catalog Number: ACM-MO-3163766
• Category: Main Products; Dendrimer Building Blocks
• Molecular Weight: 162.14 g/mol
• Molecular Formula: C9H6O3
• Synonyms: benzene-1,3,5-tricarbaldehyde
• IUPAC Name: benzene-1,3,5-tricarbaldehyde
• SMILES: O=Cc1cc(C=O)cc(C=O)c1
• InChI: 1S/C9H6O3/c10-4-7-1-8(5-11)3-9(2-7)6-12/h1-6H
• InChI Key: AEKQNAANFVOBCU-UHFFFAOYSA-N
• Boiling Point: 329.3±37.0 °C (Predicted)
• Melting Point: 156-161 °C
• Appearance: White to Almost White Powder to Crystal
• Storage: 2-8 °C
• Assay: 0.97
• Exact Mass: 162.03200
• Specific Gravity: 1.303±0.06

Case Study

Fluorescence assay of DNA nanosheets prepared using benzene-1,3,5-tricarboxyaldehyde

Mandal, Tapas Kumar, et al. Microchimica Acta 186.12 (2019): 833.

A method for preparing amino-functionalized covalent organic framework nanosheets (COF-NSs) is described. These hexagonal layered sheets are derived from phenylenediamine and benzene-1,3,5-tricarboxyaldehyde as starting materials. As an application, COF-NSs are used for sensitive and selective fluorescence assays of DNA. To achieve this, hairpin-shaped DNA probes H1 and H2 were selected; H1 uses a dye as the fluorescent probe. Upon incorporation into COF-NSs, the hairpin probe adsorbs onto the porous surface of the COFNSs. These findings were used to design a DNA assay method with a detection limit of 2 pM. This is significantly lower than the previously reported detection limit for two-dimensional nanomaterial-based fluorescent DNA.
First, p-phenylenediamine (54.07 mg, 0.5 mmol) and benzene-1,3,5-tricarboxaldehyde (81.07 mg, 0.5 mmol) were dissolved in ethanol (3.0 mL), and o-dichlorobenzene (3.0 mL) was added to the reaction mixture in a two-necked round-bottom flask. The flask was placed in an oven and heated at 120°C for 24 hours without any acid catalyst. The resulting solid was separated by centrifugation, washed with dichloromethane, acetone, and ethanol, and then dried under vacuum at 60°C for 12 hours to give a bulk COF yellow powder (81.1 mg, 82.7%) based on imine.

Monomolecular covalent honeycomb nanosheets of benzene-1,3,5-tricarboxyaldehyde on the surface of Au(111)

Kunitake, Masashi, et al. Nanoscale Advances 2.8 (2020): 3202-3208.

A two-dimensional covalent network of honeycomb nanosheets containing small 1,3,5-triaminobenzene and benzene-1,3,5-tricarboxyaldehyde aromatic building blocks was prepared in a pH-controlled aqueous solution of Au(111). In-situ scanning tunneling microscopy revealed a large, defect-free, and homogeneous honeycomb p-conjugated nanosheet at the Au(111)/liquid interface. Electrochemical potential correlations indicated that the nanosheets are based not only on reaction equilibrium but also on adsorption equilibrium, which is jointly controlled by the surface coverage of the building blocks as a function of the electrode potential.
A 0.1 M aqueous solution containing 0.1 mM 1,3,5-triaminobenzene (TAB) and benzene-1,3,5-tricarboxyaldehyde (BTA) was prepared by purification with ultrapure water. The pH was controlled between 3 and 5 by adding 0.1 mM hydrochloric acid. A bare Au(111) single crystal bead with complete surface removal was prepared. The surface was prepared by immersing the Au(111) substrate in a 10 mM KI aqueous solution and then rinsing with ultrapure water.

A covalent organic framework for capturing and converting CO2 in the synthesis of benzene-1,3,5-tricarboxaldehyde

Kunitake, Masashi, et al. Nanoscale Advances 2.8 (2020): 3202-3208.

A porous, nitrogen-rich imine-bonded covalent organic framework (COF1) was synthesized via a Schiff base condensation reaction of 4,4'-azodiphenylamine (AZO) and benzene-1,3,5-tricarboxaldehyde (BTA) under solvothermal conditions, and characterized using various techniques. Due to the presence of one-dimensional channels functionalized with basic imine (-C=N) and azo (-N=N), COF1 exhibits a high affinity for CO2, with an isotropic heat of adsorption (Qst) as high as 32.3 kJ/mol. Furthermore, ZnBr2 supported on COF1 is an excellent recyclable catalyst, enabling the cycloaddition reaction of CO2 with epoxides to generate cyclic carbonates in high yield and with 100% selectivity under mild, solvent-free conditions with 1 bar of CO2. Additionally, XPS studies and theoretical calculations confirmed the coordination of Zn(II) with the basic -C=N group. Benzene-1,3,5-tricarboxaldehyde (BTA) (0.30 mmol, 48.64 mg), diamine (4,4'-azodiphenylamine) (AZO) (0.45 mmol, 95.52 mg), 1.5 mL of mesitylene, 1.5 mL of 1,4-dioxane, and 0.5 mL of glacial acetic acid were added to a Pyrex glass tube. The mixture was sonicated for 15 minutes to obtain a homogeneous dispersion. The glass tube was then rapidly frozen in a liquid nitrogen bath, and three freeze-evacuation-thawing-degassing cycles were performed. Finally, the glass tube was sealed and heated in an oven at 393 K for 3 days. After the reaction was complete, the resulting bright red precipitate was filtered and washed with acetone and water to remove any unreacted reactants. The solid was then solvent-exchanged with acetone 8-10 times and dried under vacuum at 423 K to give COF1, with a separation yield of approximately 80%.

Organic solvent nanofiltration membranes prepared by using benzene-1,3,5-tricarboxaldehyde

Oor, Jia Zheng, et al. Journal of Membrane Science 683 (2023): 121772.

Membrane-based filtration technology offers numerous advantages, such as lower energy consumption and operating costs when separating in strong solvents. A covalent organic framework (COF)-reinforced nanofiltration (TFC) membrane was prepared by in-situ generation of benzene-1,3,5-tricarboxaldehyde (TFB) and graphene oxide (GO) in a low-toxicity solvent within an aqueous solution of p-phenylenediamine (PPD) using interfacial polymerization. The PES-COF-GO membrane exhibited optimal solvent permeability and separation efficiency at a GO content of 0.8 wt%, with a maximum water permeability of 16.2 L/m²·h·bar and a molecular weight cutoff (MWCO) of approximately 325 g·mol⁻¹. Furthermore, the cross-linked GO-COF layer endowed the membrane with chemical stability in non-polar solvents. The COF-GO layer on the PES substrate resulted in a denser surface and improved mechanical strength.
First, the PES membrane was immersed in 10 mL of a 2% PPD aqueous solution to improve its adsorption performance on the pore walls. Then, excess PPD solution was removed using a rubber roller. Next, different membrane samples were immersed in p-isopropyltoluene solutions of different concentrations of benzene-1,3,5-tricarboxaldehyde (TFB) and GO for 10 seconds to perform the inductively coupled plasma (IP) reaction. Afterward, the membrane was washed with pure p-isopropyltoluene to remove unreacted TFB and excess GO from the surface. Finally, to dry the TFC membrane, it was placed in an oven at 60°C for 10 minutes. A GO-free TFC membrane was prepared simultaneously as a baseline.

Custom Q&A

What is the molecular formula of Benzene-1,3,5-tricarboxaldehyde?

The molecular formula of Benzene-1,3,5-tricarboxaldehyde is C9H6O3.

What are the synonyms of Benzene-1,3,5-tricarboxaldehyde?

The synonyms of Benzene-1,3,5-tricarboxaldehyde are Benzene-1,3,5-tricarbaldehyde, 3163-76-6, 1,3,5-Benzenetricarboxaldehyde, and 1,3,5-TRIFORMYLBENZENE.

What is the molecular weight of Benzene-1,3,5-tricarboxaldehyde?

The molecular weight of Benzene-1,3,5-tricarboxaldehyde is 162.14 g/mol.

What is the IUPAC name of Benzene-1,3,5-tricarboxaldehyde?

The IUPAC name of Benzene-1,3,5-tricarboxaldehyde is benzene-1,3,5-tricarbaldehyde.

What is the InChI of Benzene-1,3,5-tricarboxaldehyde?

The InChI of Benzene-1,3,5-tricarboxaldehyde is InChI=1S/C9H6O3/c10-4-7-1-8(5-11)3-9(2-7)6-12/h1-6H.

What is the InChIKey of Benzene-1,3,5-tricarboxaldehyde?

The InChIKey of Benzene-1,3,5-tricarboxaldehyde is AEKQNAANFVOBCU-UHFFFAOYSA-N.

What is the canonical SMILES of Benzene-1,3,5-tricarboxaldehyde?

The canonical SMILES of Benzene-1,3,5-tricarboxaldehyde is C1=C(C=C(C=C1C=O)C=O)C=O.

What is the CAS number of Benzene-1,3,5-tricarboxaldehyde?

The CAS number of Benzene-1,3,5-tricarboxaldehyde is 3163-76-6.

What is the European Community (EC) Number of Benzene-1,3,5-tricarboxaldehyde?

The European Community (EC) Number of Benzene-1,3,5-tricarboxaldehyde is 694-839-5.

What is the topological polar surface area of Benzene-1,3,5-tricarboxaldehyde?

The topological polar surface area of Benzene-1,3,5-tricarboxaldehyde is 51.2Ų.