(2S,2'S)-2,2'-(1,2-Ethanediyldiimino)disuccinic acid (non-preferred name)(CAS: 20846-91-7)

(2S,2'S)-2,2'-(1,2-Ethanediyldiimino)disuccinic acid is a white, crystalline solid with a molecular weight of approximately 446.34 g/mol. It is slightly soluble in water and more soluble in organic solvents. This compound is known for its reactivity in forming amide bonds and ester linkages, making it useful in various synthetic applications. Its pKa values are around 3.7 and 4.6, indicating its acidity in aqueous solutions.

(2S,2'S)-2,2'-(1,2-Ethanediyldiimino)disuccinic acid can be synthesized through the condensation of diisuccinoyl chloride with ethylenediamine. This process involves the use of a condensation catalyst such as 4-dimethylaminopyridine (DMAP) or a base like triethylamine to enhance the reaction selectivity and yield. The reaction typically proceeds in an anhydrous organic solvent like dichloromethane or tetrahydrofuran at room temperature, resulting in a high yield of the desired product.

(2S,2'S)-2,2'-(1,2-Ethanediyldiimino)disuccinic acid is used in various industries. It is extensively used in the pharmaceutical sector for the synthesis of biologically active compounds, particularly in the development of peptides and proteins. In the polymer industry, it is employed as a cross-linking agent to improve the mechanical properties of polymers. Additionally, it has applications in the semiconductor industry for producing high-quality materials and in the field of sensors for detecting specific chemical analytes.

When handling (2S,2'S)-2,2'-(1,2-Ethanediyldiimino)disuccinic acid, it is essential to wear appropriate personal protective equipment (PPE), including gloves, safety goggles, and a lab coat. This compound is slightly corrosive and can cause irritation to the skin and eyes. It should be stored in a cool, dry place, away from direct sunlight and heat sources. In case of a spill, immediately clean up the area using proper spill response techniques. Always refer to the Material Safety Data Sheet (MSDS) for detailed safety information and emergency procedures.