tert-Butyl 3-carbamoylazetidine-1-carboxylate
[CAS# 486415-29-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: tert-Butyl 3-carbamoylazetidine-1-carboxylate
• Molecular Formula: C₉H₁₆N₂O₃
• Molecular Weight: 200.23
• CAS Registry Number: 486415-29-6
• EC Number: 881-843-9
• SMILES: CC(C)(C)OC(=O)N1CC(C1)C(=O)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.512, Calc.^*
• Boiling Point: 355.9±31.0 ºC (760 mmHg), Calc.^*
• Flash Point: 169.0±24.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

tert-Butyl 3-carbamoylazetidine-1-carboxylate is a chemical compound belonging to the family of azetidine derivatives, which are four-membered cyclic compounds containing one nitrogen atom. This compound contains both a carbamoyl group and a tert-butyl ester moiety, which contribute to its chemical reactivity and potential applications in various fields, including synthetic chemistry and drug development. The structure of tert-butyl 3-carbamoylazetidine-1-carboxylate provides a framework for further functionalization and modification, making it a versatile compound in organic synthesis.

The discovery of azetidine derivatives dates back to the early 20th century, when scientists first synthesized cyclic amines and explored their chemical reactivity. Azetidines like tert-butyl 3-carbamoylazetidine-1-carboxylate are of particular interest due to their ability to participate in a wide range of reactions, including nucleophilic substitutions and ring-opening reactions, due to the strained nature of their four-membered ring structure. The specific incorporation of a carbamoyl group in the 3-position of the azetidine ring adds another layer of reactivity, allowing the compound to be useful in the formation of peptide-like structures and as a precursor to other complex molecules.

One of the primary applications of tert-butyl 3-carbamoylazetidine-1-carboxylate is in the field of organic synthesis. Its ability to undergo ring-opening reactions under mild conditions makes it a valuable intermediate for the creation of larger, more complex molecules. The carbamoyl group on the azetidine ring can be readily modified to form various derivatives, which can then be further used as building blocks in the synthesis of pharmaceuticals, agrochemicals, or other functional compounds. Additionally, the tert-butyl ester group can be cleaved to reveal the carboxylate group, which can further participate in esterification reactions to form a variety of other compounds.

In medicinal chemistry, tert-butyl 3-carbamoylazetidine-1-carboxylate and its derivatives are of interest due to their potential biological activity. The presence of the carbamoyl group, which is a key feature of many biologically active molecules, suggests that this compound could have applications in the design of bioactive molecules, particularly those involved in enzyme inhibition or receptor modulation. Azetidine derivatives have been studied for their potential as antimicrobial agents, as well as for their roles in modulating various biological processes. The ability of this compound to be easily modified also makes it an attractive candidate for the development of new drugs with specific activities.

Moreover, the azetidine ring itself is a valuable scaffold in the design of peptide mimetics. The small, rigid nature of the azetidine ring provides a stable structure that can mimic peptide bonds and facilitate interactions with biological targets in a way that larger cyclic systems may not. This feature makes tert-butyl 3-carbamoylazetidine-1-carboxylate an interesting target for researchers working on drug discovery, as it could potentially be used to design small-molecule drugs that interact with specific proteins or enzymes.

In material science, derivatives of tert-butyl 3-carbamoylazetidine-1-carboxylate have been explored as potential building blocks for the development of new polymers and materials. The unique structure of azetidine derivatives, combined with their ability to undergo chemical modifications, provides opportunities for the creation of functional materials with specialized properties, such as increased stability, conductivity, or reactivity. These materials could find applications in fields such as nanotechnology, coatings, or electronics, where tailored properties are crucial.

In summary, tert-butyl 3-carbamoylazetidine-1-carboxylate is a versatile and reactive compound with significant potential in the fields of organic synthesis, medicinal chemistry, and material science. Its strained azetidine ring, combined with the functional carbamoyl and ester groups, provides a robust framework for the development of bioactive molecules, catalysts, and functional materials. As research continues into its synthesis and applications, this compound is likely to play an increasingly important role in the design of new chemical entities with diverse and valuable properties.