2,5-Diaminoterephthalic acid

• CAS: 945-30-2
• Catalog Number: ACM945302-1
• Category: Main Products
• Molecular Weight: 196.16
• Molecular Formula: C8H8N2O4
• Synonyms: 2,5-Diaminobenzene-1,4-dicarboxylic acid
• IUPAC Name: 2,5-diaminoterephthalic acid
• Canonical SMILES: C1=C(C(=CC(=C1N)C(=O)O)N)C(=O)O
• InChI: InChI=1S/C8H8N2O4/c9-5-1-3(7(11)12)6(10)2-4(5)8(13)14/h1-2H,9-10H2,(H,11,12)(H,13,14)
• InChI Key: WIOZZYWDYUOMAY-UHFFFAOYSA-N
• Melting Point: >300 °C
• Appearance: Solid
• Complexity: 230
• CompoundIs Canonicalized: Yes
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Exact Mass: 196.04840674g/mol
• Formal Charge: 0
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 4
• Isotope Atom Count: 0
• Monoisotopic Mass: 196.04840674g/mol
• Physical State: Green solid
• Rotatable Bond Count: 2
• Topological Polar Surface Area: 127Ų
• Undefined Atom Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• XLogP3: 0.7

Case Study

2,5-Diaminophthalic acid for the synthesis of metal-organic frameworks for sensing of live cancer cells

Li, Yu, et al. Sensors and Actuators B: Chemical 306 (2020): 127608.

A series of zirconium-based metal-organic frameworks (Zr-MOFs) were synthesized using 1,4-dicarbobenzene (DB), 2-aminophthalic acid (AA), and a mixture of AA and 2,5-diaminophthalic acid (DA) as ligands and developed as platforms for anchoring phosphate group-modified aptamers (UiO-66, UiO-66-NH, and UiO-66-2NH, respectively) and sensitive detection of live Michigan Cancer Foundation 7 (MCF-7) cancer cells. UiO-66-2NH has increased diversity, complexity, and amino functionality, but retains the properties of the original UiO-66. Compared with UiO-66 and UiO-66-NH, multicomponent UiO-66-2NH exhibits remarkable electrochemical activity and stronger bioaffinity to PO-Apt through π-π stacking, electrostatic interaction and covalent bonding of Zr-O-P. These advantages of UiO-66-2NH endow the corresponding aptasensor with high ability to stably form aptamer-cell complexes in aqueous solution.
To construct electrochemically efficient aptasensors for detecting living cancer cells, a series of Zr-MOFs were synthesized using 1,4-dicarbenium (DB), 2-aminophthalic acid (AA) and 2,5-diaminophthalic acid (DA) as organic ligands and explored as platforms for immobilizing aptamers in this work. Using MCF-7 cancer cells as template targets, the developed Zr-MOF-based aptasensor was assayed using both cell imaging and electrochemical techniques.

2,5-Diaminophthalic acid for the synthesis of efficient adsorbents

Zu, Jianhua, et al. Separation and Purification Technology 338 (2024): 126455.

The synthesis of the Tp-DTA framework was constructed using 1,3,5-triformylphloroglucinol (TFP) and 2,5-diaminophthalic acid (DTA), which provide large specific surface area, mesopores, and abundant coordination sites, with high adsorption capacity and special affinity for Sr. Batch adsorption experiments showed that Tp-DTA achieved a Srin alkaline solution of 145.4 mg/g and reached adsorption equilibrium within 60 minutes. The TP-DTA series showed fast kinetics for Sr, with more than 95% of Sr removed within 3 minutes. In the presence of coexisting ions (Na, K, Cs, Mg, and Ca), Tp-DTA showed excellent preferential selectivity for Srand with high removal efficiency.
The synthesis of Tp-DTATp-DTA was carried out by tautomerization via Schiff base reaction and enol-keto reaction. Dissolve a mixture of 0.30 mmol 1,3,5-triformylphloroglucinol, 0.15 mmol 2,5-diaminophthalic acid and 6 mL DMF in a 10 mL pad. Then, add acetic acid dropwise to the mixture and stir until homogeneous under ambient conditions. Afterwards, place in a stainless steel reactor and heat in a vacuum oven at 120°C for 3 days.

2,5-Diaminoterephthalic acid for photocatalytic CO2 reduction

Sun, Dengrong, et al. Chemistry-A European Journal 19.42 (2013): 14279-14285.

The metal organic framework (MOF) NH2-Uio-66(Zr) by 2,5-diaminoterephthalic acid exhibits photocatalytic reduction activity in the presence of triethanolamine as a sacrificial agent under visible light irradiation. Photoluminescence studies reveal for the first time the photoinduced electron transfer from excited 2-aminopyridine phthalate (ATA) to the Zr carbonyl cluster in NH2-Uio66(Zr). ESR analysis confirms the generation of Zr and its involvement in the photocatalytic CO2 reduction.
NH2-Uio66(Zr) was prepared following the previously reported procedure with slight modifications. ZrCl4 and 2-aminopyridine phthalic acid were dissolved in anhydrous DMF at room temperature. Deionized water was added to the mixture. The resulting mixture was stirred at room temperature for 10 min, then transferred to a 100 mL Teflon liner and heated at 120 °C for 24 h. After hydrothermal treatment, the resulting suspension was filtered, washed with DMF and methanol, extracted with methanol in a Soxhlet extractor, and dried under vacuum to obtain the product. NH2-Uio-66(Zr) was prepared together with mixed ATA and 2,5-diaminepyridinephthalic acid (DTA).

2,5-Diaminoterephthalic acid for the exploration of the slow magnetic relaxation

Oyarzabal, Itziar, et al. Magnetochemistry 7.3 (2021): 41.

A family of metal-organic frameworks with the general formula {[Nd2(ant)2((NH2)2-bdc)-
(DMF)4]·2DMF}n (1) and {[Ln2(ant)2((NH2)2-bdc)(DMF)4]·2DMF·2H2O}n (Ln = Tb (2), Ho (3), and
Er (4)) were obtained by reacting 9,10-anthracene dicarboxylic acid and 2,5-diaminoterephthalic acid with lanthanide ions in dimethylformamide (DMF). These lanthanide-organic frameworks (LnOFs) have been characterized. All LnOFs present a three-dimensional structure consisting of dinuclear entities connected by two carboxylate ligands, resulting in an open framework with DMF and water molecules located in the channels. The magnetic investigations of these LnOFs revealed a slow relaxation of magnetization over their Nd-based counterparts. These compounds also exhibited correlated photoluminescence (PL) emissions in the visible and near-infrared regions.
First, 9,10-anthracenedicarboxylic acid (4.5 mg) and 0.025 mmol of 2,5-diaminoterephthalic acid (4.5 mg) were dissolved in 2 mL of DMF in a glass vial. To this solution, 2 mL of another DMF solution containing 0.05 mmol of the corresponding lanthanide (III) nitrate salt was added dropwise, during which no precipitation was observed. After sonication of the resulting mixture for 2 min, it was placed in a sealed sample vial and heated in a column oven at 95 °C for 24 h. After this, once the mixture was slowly cooled at room temperature, polycrystalline powders were obtained for all the compounds except compound 1.

Custom Q&A

What is the molecular formula of 2,5-diaminoterephthalic acid?

The molecular formula of 2,5-diaminoterephthalic acid is C8H8N2O4.

What is the molecular weight of 2,5-diaminoterephthalic acid?

The molecular weight of 2,5-diaminoterephthalic acid is 196.16 g/mol.

When was 2,5-diaminoterephthalic acid created?

2,5-diaminoterephthalic acid was created on July 8, 2005.

When was 2,5-diaminoterephthalic acid last modified?

The last modification date of 2,5-diaminoterephthalic acid is December 2, 2023.

What is the IUPAC name of 2,5-diaminoterephthalic acid?

The IUPAC name of 2,5-diaminoterephthalic acid is "2,5-diaminoterephthalic acid".

What is the InChI of 2,5-diaminoterephthalic acid?

The InChI of 2,5-diaminoterephthalic acid is "InChI=1S/C8H8N2O4/c9-5-1-3(7(11)12)6(10)2-4(5)8(13)14/h1-2H,9-10H2,(H,11,12)(H,13,14)".

What is the InChIKey of 2,5-diaminoterephthalic acid?

The InChIKey of 2,5-diaminoterephthalic acid is "WIOZZYWDYUOMAY-UHFFFAOYSA-N".

What is the canonical SMILES of 2,5-diaminoterephthalic acid?

The canonical SMILES of 2,5-diaminoterephthalic acid is "C1=C(C(=CC(=C1N)C(=O)O)N)C(=O)O".

What is the CAS number of 2,5-diaminoterephthalic acid?

The CAS number of 2,5-diaminoterephthalic acid is 945-30-2.

What is the European Community (EC) number of 2,5-diaminoterephthalic acid?

The European Community (EC) number of 2,5-diaminoterephthalic acid is 687-048-1.