34943-06-1

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzyl-aziridine-2-carboxylic acid ethyl ester is utilized as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows it to be a valuable component in creating complex organic molecules with potential medicinal properties.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the realm of asymmetric synthesis, 1-Benzyl-aziridine-2-carboxylic acid ethyl ester serves as a chiral auxiliary. It aids in the selective formation of enantiomers, which is crucial for producing biologically active compounds with specific desired effects, as many pharmaceuticals require a specific enantiomeric form for efficacy and safety.
Used in the Preparation of Biologically Active Molecules:
This ester derivative is also employed as a precursor for the preparation of biologically active molecules. Its reactivity and structural features make it suitable for the synthesis of compounds that can interact with biological targets, potentially leading to new treatments and therapies.
Used in Organic Chemistry Research:
1-Benzyl-aziridine-2-carboxylic acid ethyl ester is a valuable compound in organic chemistry research, where it can be used to explore new reaction pathways, develop innovative synthetic methods, and understand the fundamental principles of organic reactions.
Safety Precautions:
Given its potential toxicity, 1-Benzyl-aziridine-2-carboxylic acid ethyl ester should be handled with appropriate safety measures. This includes the use of personal protective equipment, working in well-ventilated areas, and adhering to proper disposal protocols to minimize health and environmental risks.

InChI:InChI=1/C12H15NO2/c1-2-15-12(14)11-9-13(11)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3

Upstream product

• 140-88-5 ethyl acrylate 
• 3674-13-3 2,3-dibromopropionic acid ethyl ester 
• 100-46-9 benzylamine 
• 5459-35-8 2-bromo-acrylic acid ethyl ester 

Downstream Products

• 949563-17-1 (+/-)-1-benzyl-N-(1-hydroxy-2-methylpropan-2-yl)aziridine-2-carboxamide 
• 31907-93-4 1-benzylaziridine-2-carboxamide 
• 31907-94-5 1-(1-benzylaziridin-2-yl)ethan-1-one 
• 1326628-20-9 1-benzyl-N-methoxy-N-methylaziridine-2-carboxamide 
• 60692-40-2 1-benzyl-2-(1-phenylvinyl)aziridine 

Relevant academic research and scientific papers

Diaziridyl Ether of Bisphenol A

Increased complexities in applications involving curable materials virtually need new materials that can overcome the limitations of existing ones. Resins, the structure of which is based on bisphenol A backbone terminated with three membered N-heterocycles - aziridines - have been synthesized, and their thermal-curing performance in solution and solid state was evaluated by NMR and FT-IR spectroscopies, differential scanning calorimetry, and single lap shear strength test and compared with that of analogous epoxy resin (diglycidyl ether of bisphenol A; DGEBA). Results reveal that the chemical reactivity of the aziridine-based resins is fine-tunable by controlling the N-substituent of aziridine. These resins can undergo ring-opening polymerization in the presence of various curing agents under unprecedentedly mild conditions and show remarkably rapid curing rate, wide substrate scope, and excellent chemoselectivity as compared to the analogous epoxy resin. Our results demonstrate superb curing ability of aziridine, making it promising for applications in materials and polymer sciences.

The photochemical reaction of vinylaziridines and vinylazetidines with chromium(0) and molybdenum(0) (fischer) carbene complexes

The [5+2] and [6+2] cycloaddition reactions of vinylaziridines and vinylazetidines with ketenes generated photochemically from chromium(0) and molybdenum(0) Fischer carbene complexes have been investigated. These processes constitute a straightforward and

Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols

A convenient synthesis of α-(aziridin-2-yl)-α-(trifluoromethyl) alcohols starting with ethyl aziridine-2-carboxylates is reported. Grignard reaction with the corresponding Weinreb amides led to aziridin-2-yl ketones, and subsequent treatment with Ruppert-Prakash reagent gave the trimethylsilylated target compounds as mixtures of diastereoisomers, which were desilylated with TBAF. In the case of ethyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate, (S,S)- and (S,R)-aziridin-2-yl ketones were obtained, separated chromatographically and transformed into the desired enantiomerically pure α-trifluoromethylated alcohols.

Regio- and stereoselective lithiation of terminal oxazolinylaziridines: The aziridine N-substituent and the oxazolinyl group effect

The regioselective lithiation of terminal oxazolinylaziridines has been investigated. The steric hindrance of the nitrogen substituent in 1-trityl-2-oxazolinylaziridine 3a, combined with the coordinating ability of the oxazolinyl group, causes β-lithiatio

Aziridines as templates: A general strategy for the stereospecific synthesis of 2-azetidinones

Various routes to a variety of azridine-2-carboxylates have been described and the stereochemistry of these compounds has been determined by spectroscopic methods. Further, greater diversity of β-lactams via ring expansion of these azridines-2-carboxylates were obtained by a general, efficient and direct stereospecific approach.

A synthesis of aziridines from α-iodoenones

Aziridines were prepared from α-iodocycloenones in very good yield, by a Michael addition/cyclisation (Gabriel-Cromwell) process employing a slight excess of primary amine and Cs2CO3 as base at 95°C. Using chiral amines it was possible to prepare optically pure aziridines. The same method was also efficient for the synthesis of aziridines from acyclic α-halounsaturated compounds. 2-Oxoazabicycles reacted with several nucleophiles to afford α-heteroatom substituted cyclic enones in excellent yield.

N-Substituted aziridine-2-carboxylic acid derivatives and their immuno-stimulation compositions and methods

A 2-cyanaziridine derivative of the formula STR1 wherein R' is a straight-chained or branched, saturated or mono- or polyunsaturated aliphatic hydrocarbon radical with up to 8 carbon atoms, which is substituted by an aromatic nitrogen-containing heterocyclic radical with 5 or 6 ring-members and 1, 2 or 3 nitrogen atoms optionally substituted by halogen, alkoxy with up to 8 carbon atoms, alkyl with up to 8 carbon atoms, hydroxyl, carbalkoxy with up to 9 carbon atoms, carbamoyl, dialkylamino the alkyl moieties of which having up to 8 carbon atoms, cycloalkylamino, the cycloalkyl moiety having 3-10 carbon atoms, acetylamino, nitro, cyano, acetyl, alkylthio with up to 8 carbon atoms, alkylsulphinyl with up to 8 carbon atoms, alkylsulphonyl with up to 8 carbon atoms, sulphamoyl, phenyl, trifluoromethyl, phenoxy, acetoxy or methylenedioxy; or a pharmacologically acceptable salt thereof, exhibits immune stimulating activity.

N-Substituted aziridine-2-carboxylic acid derivatives for immuno stimulation

Aziridine-2-carboxylic acid derivatives of the formula STR1 wherein X is a carboxyl, nitrile, alkoxycarbonyl or carbamoyl group, and R and R1 are various organic radicals, or pharmacologically acceptable salts thereof, exhibit marked immunostimulant activity, especially in conjunction with added chemotherapeutic agents such as a penicillin, a cephalosporin, a nitrofuran or chloramphenicol. Those compounds are new where X is a cyano group or an alkoxycarbonyl radical and R1 is a hydrogen atom, but R' is not an unsubstituted alkyl radical or an alkyl radical substituted by hydroxyl, alkoxy, dialkylamino, phenyl, 4-chlorophenyl or 4-methoxyphenyl or a vinyl radical substituted by a phenyl or methyl radical, or a cycloalkyl radical, a phenyl a 4-chlorophenyl, a 4-methoxyphenyl, an s-triazinyl or a pyridinyl radical; or where X is a carbamoyl group and R1 is a hydrogen atom, R' is not an unsubstituted cyclohexyl, alkyl or benzyl radical; or where X is a cyano group or an alkoxycarbonyl radical and R1 is a phenyl radical, R' is not an isopropyl, cyclohexyl, phenyl, benzyl or p-chlorobenzyl radical; or where R1 is a methyl radical, R1 is not a benzyl, p-chloro- or p- methoxybenzyl radical.