34943-06-1

Basic information

• Product Name: 1-Benzyl-aziridine-2-carboxylic acid ethyl ester
• Synonyms: 1-Benzyl-aziridine-2-carboxylic acid ethyl ester;Ethyl 1-benzylaziridine-2-carboxylate;2-Phenyl-5-(trifluoromethyl)pyrazol-3-ol
• CAS NO: 34943-06-1
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 34943-06-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 270.719 °C at 760 mmHg
• Flash Point: 99.486 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.565
• PKA: 4.62±0.40(Predicted)
• CAS DataBase Reference: 1-Benzyl-aziridine-2-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-aziridine-2-carboxylic acid ethyl ester(34943-06-1)
• EPA Substance Registry System: 1-Benzyl-aziridine-2-carboxylic acid ethyl ester(34943-06-1)

Safety Data

• Hazardous Substances Data: 34943-06-1(Hazardous Substances Data)

Usage

General Description

1-Benzyl-aziridine-2-carboxylic acid ethyl ester is a chemical compound with the molecular formula C13H17NO3. It is an ester derivative of 1-benzylaziridine-2-carboxylic acid, and is commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds. 1-Benzyl-aziridine-2-carboxylic acid ethyl ester is a white solid at room temperature, and is soluble in organic solvents such as ethanol and dichloromethane. It has a variety of applications in the field of organic chemistry, including as a chiral auxiliary in asymmetric synthesis and as a precursor for the preparation of biologically active molecules. Additionally, it is known to exhibit some level of toxicity and should be handled with proper safety precautions.

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

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

Downstream Products

• 949563-17-1 (+/-)-1-benzyl-N-(1-hydroxy-2-methylpropan-2-yl)aziridine-2-carboxamide 
• 949563-21-7 (+/-)-2-(1-benzylaziridin-2-yl)-4,4-dimethyl-4,5-dihydrooxazole 
• 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 articles and documents

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.

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.

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.