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

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

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

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

Downstream Products

• 503-29-7 azetidine 
• 14753-26-5 3-chloropropan-1-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 
• 156-87-6 propan-1-ol-3-amine 
• 124638-48-8 1,4,8,11-tetrakis(3-toluene-p-sulfonylaminopropyl)-1,4,8,11-tetraazacyclotetradecane 
• 119345-92-5 2-acetoxy-1-(p-tolylsulfonyl)azetidine 

Relevant articles and documents

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Anionic Ring-Opening Polymerization of N-(tolylsulfonyl)azetidines to Produce Linear Poly(trimethylenimine) and Closed-System Block Copolymers

The anionic ring-opening copolymerization of N-(p-tolylsulfonyl)azetidine (pTsAzet) and N-(o-tolylsulfonyl)azetidine (oTsAzet) produces poly(pTsAzet-co-oTsAzet) as a statistical copolymer. The pTsAzet/oTsAzet copolymerization is living and allows for the synthesis of poly(sulfonylazetidine) of target molecular weights with narrow dispersities. 1H NMR spectroscopy was used to monitor the kinetics of the polymerization and estimate the monomer reactivity ratios. It was found that the reactivity ratios for oTsAzet and pTsAzet at 180 °C are 1.66 and 0.60, respectively. The tosyl groups of p(pTsAzet-co-oTsAzet) were reductively removed to produce linear poly(trimethylenimine) (LPTMI). This represents the first route to LPTMI of controlled molecular weight and low dispersity. Finally, the slow kinetics of the sulfonylazetidine polymerization facilitated the synthesis of a block copolymer without requiring the sequential addition of monomer. Specifically, pTsAzet, oTsAzet, and (N-p-toluenesulfonyl-2-methylaziridine) (pTsMAz) were combined in solution. pTsMAz selectively polymerizes to form the first block at moderate temperature. After consumption of pTsMAz, the temperature was increased to copolymerize pTsAzet and oTsAzet and produce the block copolymer p(pTsMAz)-b-p(pTsAzet-co-oTsAzet).

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Magnesium bis(monoperoxyphthalate) hexahydrate as mild and efficient oxidant for the synthesis of selenones

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

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