208034-97-3

Basic information

• Product Name: 2-Azetidinecarboxylicacid,1,1-dimethylethylester(9CI)
• Synonyms: 2-Azetidinecarboxylicacid,1,1-dimethylethylester(9CI);tert-Butyl azetidine-2-carboxylate HCl;tert-Butylazetidine-2-carboxylatehydrochloride
• CAS NO: 208034-97-3
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.21
• Product Categories: CARBOXYLICESTER
• Mol File: 208034-97-3.mol

Chemical Properties

• Boiling Point: 196.5°C at 760 mmHg
• Flash Point: 72.6°C
• Appearance: /
• Density: 1.019g/cm³
• Vapor Pressure: 0.398mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 2-Azetidinecarboxylicacid,1,1-dimethylethylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinecarboxylicacid,1,1-dimethylethylester(9CI)(208034-97-3)
• EPA Substance Registry System: 2-Azetidinecarboxylicacid,1,1-dimethylethylester(9CI)(208034-97-3)

Safety Data

• Hazardous Substances Data: 208034-97-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Azetidinecarboxylic acid, 1,1-dimethylethyl ester (9CI) is used as an intermediate in the synthesis of various pharmaceuticals for its potential to create biologically active substances. Its antioxidant properties also contribute to its potential use in developing new drugs with enhanced therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Azetidinecarboxylic acid, 1,1-dimethylethyl ester (9CI) serves as an intermediate in the production of agrochemicals, contributing to the development of effective and innovative products for agricultural applications.

InChI:InChI=1/C8H15NO2/c1-8(2,3)11-7(10)6-4-5-9-6/h6,9H,4-5H2,1-3H3

Upstream product

• 77629-96-0 2,4-dibromobutyric acid tert-butyl ester 
• 161370-66-7 (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoic acid tert-butyl ester 
• 81323-58-2 N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester 
• 34582-32-6 N-tert-butoxycarbonyl aspartic acid tert-butyl ester 
• 1173708-25-2 SES-Aze-OtBu 
• 153704-88-2 (S)-1-benzyl 2-tert-butyl azetidine-1,2-dicarboxylate 

Downstream Products

• 201283-56-9 (2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropanamido)-3-t-butoxycarbonylpropanoyl]azetidine-2-carboxylic acid t-butyl ester 

Relevant articles and documents

Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives

Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.

Ring-Strain Effects in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereocontrolled Transformations

The base-induced Sommelet–Hauser (S–H) rearrangement of azetidine-2-carboxylic acid ester-derived ammonium salts into 2-aryl-substituted derivatives was demonstrated. The ring-strain of four-membered N-heterocycles enables efficient generation of the desired ylide intermediate and enhances the rate of the S–H rearrangement. The asymmetric version of the rearrangement was characterized by excellent levels of successive chirality transmissions. The regio- and stereo-controlled nucleophilic ring opening of the rearrangement products produced quaternary α-aryl amino acid esters with excellent enantiopurities.

Direct access to L-azetidine-2-carboxylic acid

A straightforward synthesis of L-azetidine-2-carboxylic acid is described, leading to both orthogonally protected versions or totally deprotected L-Aze. The starting material is a commercially available aspartic acid derivative, whose chirality is conserv

A novel synthetic approach towards phytosiderophores: Expeditious synthesis of nicotianamine and 2'-deoxymugineic acid

A short and a novel approach for synthesis of nicotianamine, 2'- deoxymugineic acid and related phytosiderophores has been achieved through peptide intermediates. Selective amide reduction in the presence of ester functionalities by conversion to thioamid

Total Synthesis of Mugineic Acid. Efficient Use of the Phenyl Group as the Carboxyl Synthon

Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6).The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.