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

Synthesis Reference(s)

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

General Description

1-(p-Toluenesulfonyl)azetidine is a heterocyclic building block. Ag(I)-catalyzed ring-opening of 1-(p-toluenesulfonyl)azetidine (N-tosylazetidine) with alcohols, amines, thiols and related tethered 1,2-ethane dinucleophiles has been reported.

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 
• 29281-83-2 4-methylbenzensulphonamide potassium salt 
• 109-64-8 1,3-dibromo-propane 
• 98-59-9 p-toluenesulfonyl chloride 
• 143590-74-3 4-Methyl-N-(3-phenylselanyl-propyl)-benzenesulfonamide 
• 1136117-72-0 3-(4-methylphenylsulfonamido)propyl 2-(phenylethynyl)-benzoate 
• 653-37-2 perfluorobenzaldehyde 

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 
• 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 

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.