78797-58-7

Basic information

• Product Name: Azetidine, dihydrochloride
• CAS NO: 78797-58-7
• Molecular Formula: C3H7N.2ClH
• Molecular Weight: 93.5562
• Mol File: 78797-58-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Azetidine, dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Azetidine, dihydrochloride(78797-58-7)
• EPA Substance Registry System: Azetidine, dihydrochloride(78797-58-7)

Safety Data

• Hazardous Substances Data: 78797-58-7(Hazardous Substances Data)

Upstream product

• 109-77-3 malononitrile 
• 144266-58-0 3-azidopropyl diethylboronate 
• 107128-00-7 N-benzhydryl azetidine 

Downstream Products

• 147621-21-4 tert-butyl azetidine-1-carboxylate 
• 913171-51-4 {3-[4-(2-azetidin-1-yl-ethyl)-2,6-dibromo-phenoxy]-propyl}-carbamic acid tert-butyl ester 
• 918308-81-3 tert-butyl (2E)-3-(2-[4-(azetidin-1-ylmethyl)phenyl]-8-{[(4-tert-butyl-1,3-thiazol-2-yl)amino]carbonyl}-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)acrylate 
• 635309-30-7 ethyl 7-(azetidin-1-yl)-1-(2,4-dimethoxybenzyl)-5-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 1350644-49-3 4-azetidin-1-yl-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid methyl ester 
• 811794-94-2 2-(1-azetidinylmethyl)-1H-imidazole 
• 230617-65-9 1-(6-chloro-pyridin-3-ylmethyl)-azetidine 
• 863505-11-7 azetidin-1-yl-(3,4-difluoro-phenyl)-methanone 
• 863454-79-9 azetidin-1-yl-(3-chloro-4-fluoro-phenyl)methanone 
• 864245-20-5 azetidine-1-carboxylic acid [4-(4-amino-3-chlorophenoxy)pyridin-2-yl]amide 

Relevant articles and documents

SYNTHESIS OF AZETIDINE FROM 1-SUBSTITUTED AZETIDIN-3-OLS

From readily available 1-substituted azetidin-3-ols, azetidine was prepared in high yield by removal of the hydroxyl group and N-substituents.

Straightforward access to cyclic amines by dinitriles reduction

1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.

Synthesis of azetidine, pyrrolidines and piperidine by intramolecular cyclization of ω-Azidoboranes.

This paper describes the development of efficient routes to azetidine, pyrrolidines and piperidines by creation of a carbon-nitrogen bond.Two complementary syntheses of these heterocycles were studied : the cyclization of ω-azidoboronic esters by treatment with boron trichloride, and the one pot hydroboration of an ω-azidoalkene and intramolecular reductive alkylation.The scope and limitations of these two promising approaches are reported.Keywords: azides / boronic esters / boranes / intermolecular cyclization / azetidine / pyrrolidine / piperidine / pyrrolizidine