657412-79-8

Usage

Structure

Contains a benzene ring with two carboxylic acid groups, an ethyl ester group, an amino group, and a carbonyl group.

Functional Groups

Carboxylic acid, ester, amino, and carbonyl groups.

Protection

The amino and carbonyl groups are protected by the dimethylethoxy group.

Applications

Used as a building block in organic synthesis and found in various pharmaceuticals and materials.

Versatility

The chemical structure and properties make it a valuable component in the production of a wide range of products.

Molecular Weight

369.41 g/mol

Appearance

Typically a solid or crystalline substance.

Solubility

Soluble in organic solvents such as ethanol, methanol, and acetone.

Stability

Stable under normal temperature and pressure conditions, but sensitive to strong acids and bases.

Reactivity

Can undergo reactions such as esterification, amidation, and substitution due to the presence of various functional groups.

Synthesis

Typically synthesized through the reaction of 1,4-benzenedicarboxylic acid with the appropriate amine and protection group, followed by esterification with ethanol.

Purification

Can be purified through techniques such as recrystallization or column chromatography.

Safety

Handle with care, as it may have potential hazards depending on its concentration and exposure conditions. It is important to follow proper safety protocols and use appropriate personal protective equipment (PPE) when working with 1,4-Benzenedicarboxylic acid, 2-amino-5-[[(1,1-dimethylethoxy)carbonyl]amino]-, diethyl ester.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 15403-46-0 diethyl 2,5-diaminoterephthalate 

Relevant academic research and scientific papers

Diaminoterephthalate-EDTA and -EGTA Conjugates – “Turn on” Fluorescence Sensors for Zinc Ions

A highly effective “turn-on” fluorescence sensor with high selectivity for Zn2+ ions is reported. Its constitution simply consists of two units of the fluorescence dye diaminoterephthalate (DAT) and the chelate ligand EDTA. In total, four products (DAT)2EDTA and (DAT)2EGTA were prepared by conjugation of DATs with chelate ligands EDTA and EGTA as sensors for metal ions in solution. The fluorescence of all four compounds is strongly quenched by coordination of Cu2+ and Ni2+ ions. For one EDTA-derivative, the fluorescence quantum yield is increased by the factor of five with ten equivalents of ScCl3. For both EDTA derivatives, the fluorescence quantum yield increased by the factor of five with one equivalent Zn(OAc)2. Therefore, the (DAT)2EDTA structures constitute fluorescence sensors with a high selectivity for Zn2+ accompanied by a strong “turn-on” effect with Zn2+ ions. Furthermore, the coordination geometry of (DAT)2EDTA with Zn2+ was elucidated by X-ray single crystal structure analysis of the trinuclear complex [ZnCl2]{Zn(OH2)[(DAT)2EDTA – 2 H]}2 ? 6.5 H2O.

Orthogonally Protected Diaminoterephthalate Scaffolds: Installation of Two Functional Units at the Chromophore

The 2,5-diaminoterephthalate structural motif is a powerful chromophore with remarkable fluorescence properties. Containing two carboxylate and two amino functions, it defines a colored molecular scaffold which allows for orthogonal functionalization with different functional units. Therefore, different applications in life sciences and materials science could be addressed. In this study, the two amino functions were alkylated by reductive amination with side chains carrying amino (orthogonally protected as Boc or Alloc) and carboxylate functions (orthogonally protected as tBu or allyl ester). After sequential deprotections, functional units were introduced by amidation reactions. As three examples, the chromophore was coupled with retinoic acid and fullerene C60 in order to obtain a triad for studying photoinduced electron transfer processes. Furthermore, cyclooctyne and azide moieties were introduced as functional units, allowing for ligation by click reactions. These two clickable groups were applied in combination with maleimide units which are reactive toward thiol residues. The latter dyes define so-called turn on probes, since the fluorescence quantum yields increased by one order of magnitude upon reaction with the molecular target.

Hydrogen Bond-Induced Rigid Oligoanthranilamide Ribbons That Are Planar and Straight

(Matrix presented) A new series of oligoanthranilamides has been synthesized starting from suitably modified p-phenylenediamine and p-phthalic acid derivatives. Due to strong intramolecular three-center hydrogen bonds, the new oligomers self-assemble into highly stable straight and planar molecular ribbons, which have been characterized by X-ray crystallography and 1H NMR, IR, and UV-vis spectroscopy.