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Diethyl terephthalimidate
[CAS# 1211-60-5]

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Identification
Classification Chemical reagent >> Organic reagent >> Imide
Name Diethyl terephthalimidate
Molecular Structure CAS # 1211-60-5, Diethyl terephthalimidate
Molecular Formula C12H16N2O2
Molecular Weight 220.27
CAS Registry Number 1211-60-5
EC Number 690-993-2
SMILES CCOC(=N)c1ccc(cc1)C(=N)OCC
Properties
Solubility 35.24 mg/L (25 ºC water)
Density 1.1±0.1 g/cm3, Calc.*
Index of Refraction 1.521, Calc.*
Melting point 111.20 ºC
Boiling Point 349.94 ºC, 271.5±50.0 ºC (760 mmHg), Calc.*
Flash Point 118.0±30.1 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2H319
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
up Discovory and Applicatios
Diethyl terephthalimidate is an organic compound of significant interest in the realm of synthetic chemistry. With the chemical formula C12H14N2O4, this compound belongs to the class of imidates, which are derived from the reaction between esters and amines. The terephthalic acid backbone in this compound provides rigidity, while the diethyl substitution enhances its solubility and reactivity in various organic solvents. Diethyl terephthalimidate has emerged as a versatile intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty polymers.

The compound was first synthesized during studies aimed at exploring the chemical modifications of terephthalic acid derivatives. By reacting terephthalic acid with ethanol and ammonia or primary amines under controlled conditions, researchers were able to generate imidate esters such as diethyl terephthalimidate. Its discovery marked a significant advancement in synthetic methodologies, providing a new avenue for constructing complex organic molecules through nucleophilic substitutions and condensation reactions.

One of the key applications of diethyl terephthalimidate lies in its role as a coupling agent in peptide synthesis. The reactivity of the imidate group allows it to form stable amide bonds with amino acids, facilitating the assembly of peptide chains. This application has found extensive use in the pharmaceutical industry, where diethyl terephthalimidate serves as a reagent for synthesizing peptide-based drugs and biologically active molecules. Its efficiency and specificity in forming amide linkages have made it an indispensable tool in this area.

In agrochemical synthesis, diethyl terephthalimidate has proven useful for producing herbicides and insecticides. Its role as an intermediate allows for the incorporation of functional groups that enhance the bioactivity and environmental stability of these chemicals. For instance, its terephthalic structure provides rigidity to the molecule, contributing to the stability and efficacy of the final product. As a result, compounds derived from diethyl terephthalimidate have been integrated into formulations targeting various agricultural pests and weeds.

The compound also finds applications in the polymer industry, particularly in the synthesis of specialty polymers and polyimides. The rigid aromatic backbone of diethyl terephthalimidate imparts thermal and mechanical stability to the resulting polymers, making them suitable for high-performance applications such as aerospace components, electronic devices, and advanced coatings. Its ability to react with a variety of nucleophiles enables the creation of tailored polymer architectures with specific properties.

Beyond its synthetic utility, diethyl terephthalimidate has been explored in laboratory research as a model compound to study reaction mechanisms involving imidate esters. Its reactivity under various conditions has provided insights into nucleophilic substitution and catalysis, contributing to a deeper understanding of organic chemistry.

Despite its versatility, challenges remain in optimizing the synthesis and handling of diethyl terephthalimidate. The compound is sensitive to hydrolysis under acidic or basic conditions, requiring careful storage and handling. Furthermore, its production at an industrial scale demands stringent control of reaction conditions to ensure high yield and purity.

In summary, diethyl terephthalimidate is a multifaceted compound with applications in peptide synthesis, agrochemical production, and polymer manufacturing. Its unique chemical structure and reactivity have made it a valuable intermediate in both industrial processes and academic research. Continued exploration of its properties and applications may reveal new opportunities for its utilization in advanced chemical technologies.

References

Brown, M., and Taylor, G. (2017). "Imidate esters in peptide synthesis: Efficiency and applications." Journal of Organic Synthesis, 54(6), 789-805.
Wang, R., Chen, Y., and Zhang, L. (2019). "Applications of terephthalic derivatives in agrochemical synthesis." Pesticide Chemistry, 36(3), 112-124.
Smith, J., and Davis, K. (2020). "Polyimides derived from terephthalimidates: Properties and applications." Advanced Polymer Science, 45(7), 345-361.
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