2517-04-6

Basic information

• Product Name: AZETIDINE-2-CARBOXYLIC ACID
• Synonyms: Azetidinecarboxylic Acid;DL-H-Aze-OH;AZETIDINE-2-CARBO
• CAS NO: 2517-04-6
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 219-740-2
• Mol File: 2517-04-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 217°C (rough estimate)
• Boiling Point: 189.47°C (rough estimate)
• Flash Point: 100.144 °C
• Appearance: /
• Density: 1.2245 (rough estimate)
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.4340 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.35±0.20(Predicted)
• CAS DataBase Reference: AZETIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: AZETIDINE-2-CARBOXYLIC ACID(2517-04-6)
• EPA Substance Registry System: AZETIDINE-2-CARBOXYLIC ACID(2517-04-6)

Safety Data

• Hazardous Substances Data: 2517-04-6(Hazardous Substances Data)

Usage

General Description

Azetidine-2-carboxylic acid is a heterocyclic amino acid that is not found in proteins, but can be produced through the biosynthesis of the non-proteinogenic amino acid proline. It has been identified as an intermediate in the biosynthesis of the neurotransmitter, gamma-aminobutyric acid (GABA), and has also been shown to have potential pharmaceutical applications. Research has indicated that azetidine-2-carboxylic acid may have anti-tumor and anti-viral properties, as well as potential as a potent inhibitor of various enzymes. Additionally, it has been investigated for its potential in the treatment of tinnitus and diabetes. Its versatile properties and potential pharmaceutical applications make it a valuable compound for further research and development.

InChI:InChI=1/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)

Upstream product

• 56-12-2 4-amino-n-butyric acid 
• 22742-42-3 DL-N-diphenylmethylazetidine-2-carboxylic acid benzyl ester 
• 39897-13-7 1-(p-tolylsulfonyl)azetidine-2-carboxylic acid 

Downstream Products

• 134419-57-1 (2S)-methyl azetidine-2-carboxylate 
• 137441-55-5 C₃₁H₃₈N₂O₃ 
• 137441-51-1 C₂₄H₃₂N₂O₃ 
• 52162-05-7 2-amino-4-phenylthiobutanoic acid 
• 114502-03-3 4-amino-2-phenylthiobutanoic acid 
• 174740-81-9 N-benzyloxycarbonyl-(S)-(-)-2-azetidine-carboxylic acid 
• 228857-58-7 (R)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid 
• 647854-63-5 methyl (2R)-azetidine-2-carboxylate hydrochloride 
• 159749-28-7 1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid 
• 51077-14-6 (S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid 
• 161511-85-9 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 1155286-71-7 1-{5-[4-(3-chloro-phenyl)-5-fluoro benzothiazol-6-ylmethyl]-pyridin-2-yl}-azetidine-2-carboxylic Acid 
• 1155877-05-6 1-[5-(3'-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-azetidine-2-carboxylic acid 
• 1155877-43-2 1-[5-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyrimidin-2-yl]-azetidine-2-carboxylic acid 

Relevant articles and documents

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).

Solid-Liquid Biphasic Hydroformylation of Olefins Catalyzed by Rhodium Carhonyl Complexes

Some polymer-anchored alkenes have been hydroformylated by carrying out the reaction in a high-pressure reactor equipped with a suitably designed vial. The solid substrates are converted to the corresponding oxo-aldehydes in high yields. In all cases the regioselectivity was strongly shifted towards the linear aldehyde when the rhodium carbonyl complex was modified with xantphos (3:1 or 4:1 P/Rh molar ratio). Treatment with 5% of trifluoroacetine acid in dichloromethane at room temperature removed quantitatively the oxo-product from the polymer support, which can be purified and reused.

Process for the production of enantiomerically-pure azetidine-2-carboxylic acid

The invention relates to a process for the production of enantiomerically-pure AzeOH which comprises selective crystallisation of a diastereomerically-pure tartrate salt thereof, followed by liberation of the free amino acid, as well as the compounds L-azetidine-2-carboxylic acid-D-tartrate and D-azetidine-2-carboxylic acid-L-tartrate.