1-(P-TOSYL)AZIRIDINE

Base Information

• Chemical Name: 1-(P-TOSYL)AZIRIDINE
• CAS No.: 3634-89-7
• Molecular Formula: C9H11NO2S
• Molecular Weight: 197.258
• Hs Code.: 2933990090
• Mol file: 3634-89-7.mol

Synonyms:1-(P-TOSYL)AZIRIDINE;1-(4-methylphenyl)sulfonylaziridine;

Chemical Property of 1-(P-TOSYL)AZIRIDINE

Chemical Property:

• Melting Point: 52-56 °C
• Boiling Point: 322.3±35.0 °C(Predicted)
• PKA: -6.46±0.20(Predicted)
• PSA: 45.53000
• Density: 1.334±0.06 g/cm3(Predicted)
• LogP: 2.01800
• Storage Temp.: ?20°C

Purity/Quality:

97% ^*data from raw suppliers

1-[(4-METHYLBENZENE)SULFONYL]AZIRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 154388
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reagent for beta-aminoethylation as well as for chemical fixation of carbon dioxide via ring expansion reaction under atmospheric pressure. Reagent for beta-aminoethylation

Technology Process of 1-(P-TOSYL)AZIRIDINE

There total 28 articles about 1-(P-TOSYL)AZIRIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-<2-(Phenylseleno)ethyl>-p-toluenesulfonamide (136573-35-8) → N-(p-toluenesulfonyl)aziridine (3634-89-7)

Guidance literature:

With potassium hydroxide; 3-chloro-benzenecarboperoxoic acid; In isopropyl alcohol; for 1h; Ambient temperature;

DOI:10.1016/0040-4039(92)88089-N

Reference yield: 99.0%

2-(tosylamino)ethyl p-toluenesulfonate (6367-75-5) → N-(p-toluenesulfonyl)aziridine (3634-89-7)

Guidance literature:

With potassium hydroxide; In water; toluene; for 2h;

DOI:10.1002/hlca.19850680202

Reference yield: 99.0%

N-tosyl-1,2-oxazetidine → N-(p-toluenesulfonyl)aziridine (3634-89-7)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201500731

upstream raw materials:

ethyleneimine

p-toluenesulfonyl chloride

N-(2-chloroethyl)-4-methylbenzenesulfonamide

N-(2-bromo-ethyl)-4-methyl-benzenesulfonamide

Downstream raw materials:

4-methyl-N-(2-(thiophen-2-yl)ethyl)benzenesulfonamide

1,4,8,11-tetrakis(2-p-toluenesulfonamidoethyl)-1,4,8,11-tetraazacyclotetradecane

C₄₂H₆₀N₆O₈S₄

4-(2-tosylaminoethyl)-1,7,11-tritosyl-1,4,7,11-tetraazacyclotetradecane

Refernces

Birch reductive alkylation of biaryls: Scope and limitations

10.1021/jo901395m

The research study on the Birch Reductive Alkylation (BRA) of biaryls, focusing on the scope and limitations of this method for synthesizing symmetrical arylcyclohexadienes, which are valuable building blocks for the synthesis of alkaloids. The purpose of the research was to investigate the regioselectivity of the BRA process by varying the nature of substituents on the aromatic rings of biaryls, particularly electron-rich substituents like OMe, OH, and NR2 groups. The study concluded that high levels of regiocontrol could be achieved through careful selection of substituents, and that the BRA method is a valuable tool for organic synthesis, offering a straightforward entry toward cyclohexa-2,5-dienyl arene systems bearing a quaternary center. Key chemicals used in the process included various biaryl precursors, lithium in ammonia as the reducing agent, and a range of electrophiles such as R-chloroacetonitrile, N-tosylaziridine, esters, amides, nitriles, epoxides, acetals, and sterically hindered t-Bu groups and cyclopropyl substituents.

Ag(I)-catalyzed regioselective ring-opening of N -tosylaziridine and N -tosylazetidine with S -, O -, and N -nucleophiles and tethered dinucleophiles

10.1021/jo102285z

The research focuses on the Ag(I)-catalyzed regioselective ring-opening of N-tosylaziridines and N-tosylazetidines with various S-, O-, and N-nucleophiles, as well as tethered dinucleophiles. The experiments utilized [Ag(COD)2]PF6 as a catalyst to facilitate the ring-opening reactions with nucleophiles such as alcohols, amines, thiols, and related 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluations of stepwise energetics were conducted to understand the relationship between nucleophilic reactivity and binding affinity to cationic Ag(I). The study suggests an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I). The analysis involved monitoring reactions using 1H NMR, and the products were purified and characterized using column chromatography and NMR spectroscopy. The research also explored the substrate scope and functional group selectivity, yielding a range of 1,2-amino ethers, diamines, amino thioethers, and 1,3-amino ethers in good to excellent yields.

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