67160-49-0

Basic information

• Product Name: 1-benzyl-3-methanesulfonyloxyazetidine
• Synonyms: 1-benzyl-3-methanesulfonyloxyazetidine;1-benzyl-3-Methanesulfonyloxyazetidine,N-benzyl-3-Methanesulfonyloxyazetidine;N-Benzyl-3-(mesyloxy)azetidine
• CAS NO: 67160-49-0
• Molecular Formula: C₁₁H₁₅NO₃S
• Molecular Weight: 241.3067
• Mol File: 67160-49-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 137-138℃
• Boiling Point: 384.8 °C at 760 mmHg
• Flash Point: 186.5 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 3.98E-06mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 1-benzyl-3-methanesulfonyloxyazetidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-3-methanesulfonyloxyazetidine(67160-49-0)
• EPA Substance Registry System: 1-benzyl-3-methanesulfonyloxyazetidine(67160-49-0)

Safety Data

• Hazardous Substances Data: 67160-49-0(Hazardous Substances Data)

Usage

General Description

1-Benzyl-3-methanesulfonyloxyazetidine is a chemical compound also known as BnMesOAz. It is a sulfonamide-based reagent that is commonly used in organic synthesis for the selective introduction of the azetidine ring. 1-Benzyl-3-methanesulfonyloxyazetidine exhibits strong reactivity towards a variety of nucleophiles, making it useful in a range of chemical reactions such as ring-opening reactions and the preparation of complex organic molecules. Additionally, 1-Benzyl-3-methanesulfonyloxyazetidine has been found to be an effective reagent for the synthesis of various biologically active compounds, demonstrating its potential in medicinal chemistry and drug discovery research.

InChI:InChI=1/C11H15NO3S/c1-16(13,14)15-11-8-12(9-11)7-10-5-3-2-4-6-10/h2-6,11H,7-9H2,1H3

Upstream product

• 54881-13-9 N-benzyl-3-hydroxyazetidine 
• 124-63-0 methanesulfonyl chloride 
• 75605-52-6 N-benzyl-3-amino-1-chloropropan-2-ol 
• 100-46-9 benzylamine 
• 223382-13-6 1-benzylazetidine-3-ol hydrochloride 

Downstream Products

• 156521-27-6 dimethyl 2-(1-benzyl-3-azetidinyl)propane-1,3-dioate 
• 1307683-82-4 N-(1-benzylazetidin-3-yl)acetamide 

Relevant articles and documents

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

DERIVATIVES OF 6-(2,3-DICHLOROPHENYL)-1,2,4-TRIAZIN-5- AMINE

The instant disclosure relates to (among other things) compounds that are derivatives of 6-(2,3-dichlorophenyl)-1,2,4-triazin-5-amine. The compounds provided possess unique effects and differences over other phenyltriazines known in the art.

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.