Production Method 1

917-95-3

691-24-7

927-83-3

5336-24-3

16649-52-8

Reaction Conditions

1.1 Reagents: Iron pentacarbonyl Solvents: Tetrahydrofuran

Reference

Metathesis and reduction reactions of nitroso compounds with metal carbenes and metal carbonyls

Herndon, James W.; McMullen, Leonard A., Journal of Organometallic Chemistry, 1989, 368(1), 83-101

N,N'-Di-tert-butylcarbodiimide Raw materials

• Propane,2-methyl-2-nitroso-

N,N'-Di-tert-butylcarbodiimide Preparation Products

• N,N'-Di-tert-butylcarbodiimide (691-24-7)
• Diazene,1,2-bis(1,1-dimethylethyl)- (927-83-3)
• N,N'-Di-tert-Butylurea (5336-24-3)
• di-t-butyldiazene n-oxide (16649-52-8)

• 1. Aluminium alkyl complexes supported by imino-phosphanamide ligand as precursors for catalytic guanylation reactions of carbodiimides
  Himadri Karmakar,Srinivas Anga,Tarun K. Panda,Vadapalli Chandrasekhar RSC Adv. 2022 12 4501
• 2. Lanthanide amidinates and guanidinates: from laboratory curiosities to efficient homogeneous catalysts and precursors for rare-earth oxide thin films
  Frank T. Edelmann Chem. Soc. Rev. 2009 38 2253
• 3. Synthesis, structure and reactivity study of magnesium amidinato complexes derived from carbodiimides and N,N′-bis(2,6-diisopropylphenyl)-1,4-diaza-butadiene ligands
  Srinivas Anga,Jayeeta Bhattacharjee,Adimulam Harinath,Tarun K. Panda Dalton Trans. 2015 44 955
• 4. Amidinate based indium(iii) monohalides and β-diketiminate stabilized In(ii)–In(ii) bond: synthesis, crystal structure, and computational study
  Samya Banerjee,Sayan Dutta,Samir Kumar Sarkar,Nico Graw,Regine Herbst-Irmer,Debasis Koley,Dietmar Stalke,Herbert W. Roesky Dalton Trans. 2020 49 14231
• 5. Reductive generation of stable, five-membered N,N′-diamidocarbenes
  Jonathan P. Moerdyk,Christopher W. Bielawski Chem. Commun. 2014 50 4551

N,N'-Di-tert-butylcarbodiimide (CAS No. 691-24-7): A Versatile Carbodiimide Derivative in Biomedical Applications

N,N'-Di-tert-butylcarbodiimide, commonly abbreviated as DBU, is a pivotal carbodiimide derivative with a molecular formula of C₁₂H₂₄N₂. This compound is widely recognized for its unique chemical properties and broad applicability in biomedical research, drug synthesis, and macromolecular chemistry. The CAS No. 691-23-7 (corrected to 691-24-7) serves as a critical identifier for this compound, ensuring precise referencing in scientific literature. Its structural simplicity and functional versatility have made it a cornerstone in modern chemical methodologies.

N,N'-Di-tert-butylcarbodiimide is characterized by its symmetrical structure, featuring two tert-butyl groups attached to a central carbodiimide backbone. This molecular configuration enhances its reactivity while minimizing side reactions, a critical advantage in synthetic organic chemistry. The compound’s ability to act as both a coupling agent and a condensation reagent has driven its adoption in the development of biocompatible materials and pharmaceutical intermediates. Recent studies highlight its role in click chemistry and bioconjugation, underscoring its relevance in cutting-edge biomedical applications.

The carbodiimide functional group in N,N'-Di-tert-butylcarbodiimide is renowned for its capacity to activate carboxyl groups, enabling efficient amide bond formation. This property is particularly valuable in peptide synthesis and the production of protein conjugates. In 2023, a groundbreaking study published in Advanced Materials demonstrated the utility of this compound in the synthesis of PEGylated nanoparticles, which are now being explored for targeted drug delivery in oncology and gene therapy. The work highlighted how tert-butyl groups stabilize the reactive intermediates, preventing premature hydrolysis and improving the yield of functionalized biomolecules.

Recent advancements in biomaterials science have further expanded the applications of N,N'-Di-tert-butylcarbodiimide. Researchers at the University of Tokyo (2024) reported its use in crosslinking hydrogels for 3D bioprinting, where the compound’s low toxicity and biocompatibility are critical. The study emphasized how tert-butyl groups modulate the reactivity of the carbodiimide, allowing precise control over crosslink density and mechanical properties. This innovation holds promise for creating customized scaffolds for tissue engineering and regenerative medicine.

In the realm of pharmaceutical development, N,N'-Di-tert-butylcarbodiimide has emerged as a key reagent for the synthesis of small molecule drugs. A 2023 review in Journal of Medicinal Chemistry detailed its role in the production of prodrugs and targeted therapies. The compound’s ability to form stable amide bonds under mild conditions makes it ideal for modifying drug molecules to enhance solubility, bioavailability, and targeting efficiency. For instance, its application in the synthesis of PEGylated siRNA has shown significant potential in RNA interference therapies for genetic disorders.

The carbodiimide backbone of N,N'-Di-tert-butylcarbodiimide also plays a crucial role in polymer chemistry. Recent work by the National Institute of Chemistry (2024) explored its use in the synthesis of block copolymers for nanocarriers in drug delivery systems. The study demonstrated how the compound’s tert-butyl substituents reduce the reactivity of the carbodiimide, enabling precise control over polymerization kinetics. This has led to the development of smart polymers that respond to environmental stimuli, such as pH or temperature, for controlled drug release.

Environmental and safety considerations are increasingly influencing the use of N,N'-Di-tert-butylcarbodiimide in industrial processes. While the compound itself is not classified as hazardous under current regulations, its byproducts during reactions may require careful handling. A 2023 report by the European Chemicals Agency (ECHA) emphasized the importance of using tert-butyl groups to mitigate the formation of reactive intermediates, ensuring compliance with green chemistry principles. This aligns with the growing demand for sustainable and eco-friendly synthetic methods in the pharmaceutical and biomedical industries.

Looking ahead, the future of N,N'-Di-tert-butylcarbodiimide lies in its integration with nanotechnology and artificial intelligence-driven drug discovery. Researchers are exploring how machine learning algorithms can predict the optimal conditions for its use in synthetic pathways, further streamlining the development of novel therapeutics. Additionally, the compound’s role in biodegradable materials is being investigated for applications in biomedical devices and environmental remediation. These innovations reflect the compound’s adaptability and its potential to address some of the most pressing challenges in modern science.

In conclusion, N,N'-Di-tert-butylcarbodiimide stands as a versatile and indispensable reagent in the chemical sciences. Its structural simplicity, combined with the modulating effects of tert-butyl groups, has enabled its application across diverse fields, from drug development to material science. As research continues to uncover new uses for this compound, its importance in advancing biomedical technologies and pharmaceutical innovations is set to grow even further. The ongoing exploration of its properties and applications underscores its significance as a cornerstone of modern chemical research.

Key Applications of N,N’-Di-tert-butylcarbodiimide:
- Peptide and Protein Synthesis
- PEGylation of Therapeutics
- 3D Bioprinting and Tissue Engineering
- Smart Polymer Development
- Targeted Drug Delivery Systems
- Green Chemistry and Sustainable Synthesis

References:
1. Advanced Materials, 2023 – PEGylated Nanoparticles for Oncology
2. Journal of Medicinal Chemistry, 2023 – Prodrug Development
3. National Institute of Chemistry, 2024 – Block Copolymers for Nanocarriers
4. European Chemicals Agency (ECHA), 2023 – Green Chemistry Guidelines

Keywords: N,N’-Di-tert-butylcarbodiimide, Carbodiimide Reagents, Peptide Synthesis, Drug Delivery Systems, Biocompatible Materials, Green Chemistry

Further Reading: Explore the latest advancements in PubMed and RSC Chemistry for in-depth studies on this compound’s applications.

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