54881-13-9

Basic information

• Product Name: 1-Benzylazetidin-3-ol
• Synonyms: N-BENZYL-3-HYDROXYAZETIDINE;1-BENZYLAZETIDINE-3-OL;1-BENZYL AZETIDINE-3-OL 98%;1-Benzyl-3-hydroxyazetidine;1-Benzylazetidin-3-ol;3-Azetidinol, 1-(phenylmethyl)-;1-Benzyl-3-azetidinol;1-Benzyl-3-hydroxyazetidi...
• CAS NO: 54881-13-9
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• Product Categories: Heterocyclic Compounds
• Mol File: 54881-13-9.mol

Chemical Properties

• Melting Point: 64-65 °C
• Boiling Point: 259.17 °C at 760 mmHg
• Flash Point: 105.864 °C
• Appearance: /
• Density: 1.189 g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 14.33±0.20(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1-Benzylazetidin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzylazetidin-3-ol(54881-13-9)
• EPA Substance Registry System: 1-Benzylazetidin-3-ol(54881-13-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 54881-13-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1-Benzylazetidin-3-ol is used as a building block in pharmaceutical research for its potential to contribute to the development of new drugs. Its unique structure allows for the creation of novel compounds with possible therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 1-Benzylazetidin-3-ol is utilized as a key intermediate, enabling the construction of complex organic molecules that may have various applications in different industries.
Used in Alzheimer's Disease Research:
1-Benzylazetidin-3-ol is used as a potential anti-Alzheimer's agent due to its cholinesterase inhibitory properties. This makes it a valuable compound for research into treatments for neurodegenerative diseases, particularly Alzheimer's, where enhancing cholinergic function is a recognized therapeutic strategy.
Used in Neuropharmacology:
As a cholinesterase inhibitor, 1-Benzylazetidin-3-ol is employed in neuropharmacological research to study its effects on the nervous system. This could lead to insights into the development of drugs that can improve cognitive function and treat conditions related to cognitive decline.

InChI:InChI=1/C10H13NO/c12-10-7-11(8-10)6-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2

Upstream product

• 111043-42-6 N-benzyl-3-(trimethylsilyloxy)azetidine 
• 100-46-9 benzylamine 
• 75-56-9 methyloxirane 
• 80236-09-5 N-benzyl-1-(oxiran-2-yl)methanamine 
• 28659-12-3 1,3-dichloro-2-(6-(3,4,5,6-tetrahydro-2H-pyranoxy))propane 
• 106-89-8 epichlorohydrin 
• 111043-32-4 1-benzyl-(3-chloro-2-trimethylsilyloxypropyl)-amine 
• 75605-52-6 N-benzyl-3-amino-1-chloropropan-2-ol 

Downstream Products

• 858940-94-0 N-benzyl-3-bromoazetidine 
• 56862-39-6 3-(N-benzyl-N-methyl)amino-2-chloro-1-propene 
• 1307683-82-4 N-(1-benzylazetidin-3-yl)acetamide 
• 1365212-21-0 C₁₃H₁₈N₂O 
• 223382-13-6 1-benzylazetidine-3-ol hydrochloride 
• 141699-55-0 tert-butyl 3-hydroxyazetidine-1-carboxylate 
• 18621-18-6 azetion-3-ol hydrochloride 
• 878391-51-6 1-benzyl-3-acetylthio-azetidine 
• 67160-49-0 1-benzyl-3-methanesulfonyloxyazetidine 
• 685891-48-9 1-benzyl-3-chloroazetidine 
• 156303-83-2 1-benzyl-3-azetidinone 

Relevant articles and documents

Preparation method of 2-[1-(ethyl sulfonyl)-3-azacyclic butyl] acetonitrile

The invention relates to the technical field of medical chemistry, and particularly relates to a preparation method of a baricotinib tetratomic ring intermediate, and also provides green oxidizing reaction performed in a micro-channel reactor. According to the method, the raw materials in the technical route are easily obtained; the method is economic, green, environmentally friendly and suitablefor industrial production.

Development of an optimized process for the preparation of 1-benzylazetidin-3-ol: An industrially important intermediate for substituted azetidine

A thoroughly optimized and robust process for the synthesis of 1-benzylazetidin-3-ol has been emphasized. 1-Benzylazetidin-3-ol has been utilized as a starting material in the commercial synthesis of azetidin-3-ol hydrochloride. Synthesis of azetidin-3-ol hydrochloride involves the usage of very low cost and commercially available starting material (benzylamine) and with reduced formation of di(3-chloro-2-hydroxypropyl) benzylamine significantly resulting in an economical process that allows the effective production of 1-benzyl azetidin-3-ol as well as azetidin-3-ol hydrochloride.

ACID ADDITION SALTS OF SYNTHETIC INTERMEDIATES FOR CARBAPENEM ANTIBIOTICS AND PROCESSES FOR PREPARING THE SAME

The present invention provides a process for preparing an acid addition salt of a synthetic intermediate for carbapenem antibiotics and a novel acid addition salt of a synthetic intermediate for carbapenem antibiotics obtained from the process. The present invention also provides a process for preparing a carbapenem antibiotic using the acid addition salt. According to the process of the present invention, an acid addition salt of a synthetic intermediate for carbapenem antibiotics can be prepared in a high yield and high purity, without conducting column chromatography. Thus, the process of the present invention can be applied to mass production with an industrial scale. Furthermore, since the acid addition salts have solid forms, they are easy to handle and keep in a manufacturing site.

ACID ADDITION SALTS OF SYNTHETIC INTERMEDIATES FOR CARBAPENEM ANTIBIOTICS AND PROCESSES FOR PREPARING THE SAME

The present invention provides a process for preparing an acid addition salt of a synthetic intermediate for carbapenem antibiotics and a novel acid addition salt of a synthetic intermediate for carbapenem antibiotics obtained from the process. The present invention also provides a process for preparing a carbapenem antibiotic using the acid addition salt. According to the process of the present invention, an acid addition salt of a synthetic intermediate for carbapenem antibiotics can be prepared in a high yield and high purity, without conducting column chromatography. Thus, the process of the present invention can be applied to mass production with an industrial scale. Furthermore, since the acid addition salts have solid forms, they are easy to handle and keep in a manufacturing site.

PREPARATION OF PYRIDONECARBOXYLIC ACID ANTIBACTERIALS

A process for making 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, and therapeutically acceptable salts thereof, and intermediates used in the process are disclosed.

A practical and facile synthesis of azetidine derivatives for oral carbapenem, L-084

An orally active carbapenem L-084, which exhibits high bioavailability in humans, has a 1-(1,3-thiazolin-2-yl)azetidin-3-ylthio moiety at the C-2 position of the 1β-methylcarbapenem skeleton. We established a practical and cost-effective synthesis of 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine (1) for further scale-up production of L-084. This synthesis method entails an industry-oriented reaction of azetidine ring-closure to yield N-benzyl-3-hydroxyazetidine (16), which is eventually converted to 1 via key intermediates, Bunte salts 19 and 20.

2-ARYLMETHYLAZETIDINE CARBAPENEM DERIVATIVES AND PREPARATION THEREOF

A 2-arylmethylazetidine carbapenem derivative of formula ( I ) or a pharmaceutically acceptable salt thereof exhibits a wide spectrum of antibacterial activities against Gram-positive and Gram-negative bacteria and excellent antibacterial activities against resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) and quinolone-resistant strains (QRS).

New Synthesis of Propargylic Amines from 2-(Bromomethyl)aziridines. Intermediacy of 3-Bromoazetidinium Salts

A new, efficient, and straightforward synthesis provides propargylamines in high overall yields (64-77%) by transformation of 1-(arylmethyl)-2-(bromomethyl)aziridines into N,N-di(arylmethyl)N-(2-propynyl)amines via N-(2,3-dibromopropyl)amines and N-(2-bromo-2-propenyl)amines. The conversion of N-(2,3-dibromopropyl)amines into N-(2-bromo-2-propenyl)amines is based on a novel analogue of the Hofmann elimination. A Yamaguchi-Hirao alkylation, a Sonogashira coupling, or a hydroarylation reaction further functionalized these propargylamines toward potentially interesting compounds for medicinal and agrochemical use.

Facile Syntheses of Azetidin-3-ols by Rearrangement of 2,3-Epoxypropylamines

The N-alkyl-2,3-epoxypropylamines (2) formed from primary alkylamines (1) and epichlorohydrin were chemoselectively rearranged to the four-membered rings, N-alkylazetidin-3-ols (3), upon treatment of triethylamine in refluxing acetonitrile.

Novel Syntheses of 1,3,3-Trinitroazetidine

Alternative methods for the synthesis of 1,3,3-trinitroazetidine (TNAZ) from epichlorohydrin, and benzhydrylamine have been developed.These approaches employ N-sulfonyl-3-(hydroxyimino)azetidines as penultimate intermediates and represent an improvement over previously published methods which require either diazo containing intermediates or involve low yielding procedures.Parallel methods employing N-benzhydryl- and N-benzyl-3-(hydroxyimino)azetidine were also investigated as alternate routes to TNAZ