7730-45-2

Basic information

• Product Name: 1-(P-TOLYLSULFONYL)AZETIDINE
• Synonyms: 1-(P-TOLYLSULFONYL)AZETIDINE;1-(p-Toluenesulfonyl)azetidine;1-(toluene-4-sulfonyl)azetidine;1-tosylazetidine;1-(4-Methylphenyl)sulfonylazetidine
• CAS NO: 7730-45-2
• Molecular Formula: C₁₀H₁₃NO₂S
• Molecular Weight: 211.28
• Mol File: 7730-45-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 119-122 °C(lit.)
• Boiling Point: 337.6°Cat760mmHg
• Flash Point: 158°C
• Appearance: /
• Density: 1.276g/cm³
• Vapor Pressure: 0.000104mmHg at 25°C
• Refractive Index: 1.59
• BRN: 177046
• CAS DataBase Reference: 1-(P-TOLYLSULFONYL)AZETIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(P-TOLYLSULFONYL)AZETIDINE(7730-45-2)
• EPA Substance Registry System: 1-(P-TOLYLSULFONYL)AZETIDINE(7730-45-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 7730-45-2(Hazardous Substances Data)

Usage

Description

1-(P-Toluenesulfonyl)azetidine, also known as N-tosylazetidine, is a heterocyclic building block that plays a crucial role in organic synthesis. It is characterized by the presence of a tosyl (p-toluenesulfonyl) group attached to a four-membered azetidine ring. This unique structure allows for versatile chemical reactions and applications in various fields.

Uses

Used in Organic Synthesis:
1-(P-Toluenesulfonyl)azetidine is used as a key intermediate in the synthesis of various heterocyclic compounds and pharmaceuticals. Its reactivity and stability make it a valuable building block for the development of novel molecules with potential applications in medicine, materials science, and other areas.
Used in Ring-Opening Reactions:
1-(P-Toluenesulfonyl)azetidine is used as a substrate in Ag(I)-catalyzed ring-opening reactions with nucleophiles such as alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. These reactions allow for the formation of new carbon-carbon and carbon-heteroatom bonds, expanding the scope of synthetic routes to complex molecules.
Used in Medicinal Chemistry:
1-(P-Toluenesulfonyl)azetidine is used as a starting material for the synthesis of biologically active compounds, including potential drug candidates. Its ability to participate in various chemical transformations enables the creation of diverse molecular structures with potential therapeutic properties.
Used in Materials Science:
1-(P-Toluenesulfonyl)azetidine can be employed in the development of novel materials with specific properties, such as polymers, dendrimers, and other macromolecular structures. Its versatility in chemical reactions allows for the design of materials with tailored characteristics for various applications, including sensors, catalysts, and advanced materials for energy storage and conversion.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 138, 1961 DOI: 10.1021/jo01060a033

InChI:InChI=1/C10H13NO2S/c1-9-3-5-10(6-4-9)14(12,13)11-7-2-8-11/h3-6H,2,7-8H2,1H3

Upstream product

• 13379-99-2 N-(3-chloropropyl)-4-methylbenzenesulfonamide 
• 503-29-7 azetidine 
• 51425-88-8 N-tosyl 3-tosylate-1-propylamine 
• 3245-95-2 N-(3-bromo-propyl)-4-methyl-benzenesulfonamide 
• 5469-66-9 propane-1,3-diol ditosylate 
• 70-55-3 toluene-4-sulfonamide 
• 143590-74-3 4-Methyl-N-(3-phenylselanyl-propyl)-benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 29281-83-2 4-methylbenzensulphonamide potassium salt 
• 109-64-8 1,3-dibromo-propane 
• 653-37-2 perfluorobenzaldehyde 
• 1136117-72-0 3-(4-methylphenylsulfonamido)propyl 2-(phenylethynyl)-benzoate 

Downstream Products

• 503-29-7 azetidine 
• 119345-92-5 2-acetoxy-1-(p-tolylsulfonyl)azetidine 
• 124638-48-8 1,4,8,11-tetrakis(3-toluene-p-sulfonylaminopropyl)-1,4,8,11-tetraazacyclotetradecane 
• 14753-26-5 3-chloropropan-1-amine 
• 156-87-6 propan-1-ol-3-amine 
• 1158201-42-3 N-1-[3-(1H-indol-3-yl)propyl]-4-methyl-1-benzenesulfonamide 
• 1158201-47-8 N-1-[3-(2-methyl-1H-3-indoyl)propyl]-4-methyl-1-benzenesulfonamide 
• 1158201-44-5 N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-methylbenzenesulfonamide 
• 1158201-55-8 C₂₀H₂₄N₂O₂S 
• 1158201-48-9 C₂₀H₂₄N₂O₂S 
• 1158201-53-6 C₂₁H₂₄N₂O₄S 
• 1158201-50-3 4-methyl-N-(3-(5-methyl-1H-indol-3-yl)propyl)benzenesulfonamide 

Relevant articles and documents

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution

The synthesis of benzosultams has been achieved through a gold(I)-catalyzed ammonium formation strategy. Starting from easily available N-(2-alkynyl)phenylsulfonyl azetidine derivatives, a cyclization reaction generated a spiroammonium gold intermediate t

HBr–DMPU: The First Aprotic Organic Solution of Hydrogen Bromide

HBr and DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone) form a room-temperature-stable complex that provides a mild, effective, and selective hydrobrominating reagent toward alkynes, alkenes, and allenes. HBr–DMPU could also replace other halogenating reagents in the halo-Prins reaction, ether cleavage, and deoxy-bromination reactions.

Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.