18366-49-9

Usage

Cyclic organic compound

A compound consisting of a closed loop or ring of atoms, in this case, a three-membered aziridine ring.

Three-membered aziridine ring

A small ring structure containing three atoms, specifically nitrogen and two carbon atoms, which is a characteristic feature of 1-tert-butyl-2-phenylaziridine.

tert-Butyl group

A group consisting of three methyl (CH3) groups attached to a single carbon atom, which is attached to the aziridine ring in 1-tert-butyl-2-phenylaziridine.

Phenyl group

A benzene ring (a six-carbon ring with alternating single and double bonds) attached to the aziridine ring, which contributes to the compound's structure and reactivity.

Reagent in organic synthesis

1-tert-butyl-2-phenylaziridine is commonly used as a reagent to facilitate chemical reactions, particularly in the preparation of chiral amine derivatives.

Chiral amine derivatives

The compound is used to synthesize amines with a specific three-dimensional arrangement of atoms, which can be important for their biological activity and potential pharmaceutical applications.

Potential applications in pharmaceutical chemistry

The compound can be used as a building block for the synthesis of bioactive molecules, which may have therapeutic effects or other beneficial properties.

Polymerization inhibitor

1-tert-butyl-2-phenylaziridine is known for its potential use in inhibiting polymerization reactions in various industrial processes, which can be important for controlling the properties of materials and preventing unwanted side reactions.

Hazards to human health and the environment

Proper handling and management of 1-tert-butyl-2-phenylaziridine are essential, as it may pose risks to human health and the environment if not managed correctly.

Upstream product

• 14467-32-4 2-(tert-butylamino)-1-phenylethan-1-ol 
• 36378-98-0 S-(dimethylamino)-S-phenyl(trans-2-phenyleth-1-enyl)oxosulfonium fluoroborate 
• 75-64-9 tert-butylamine 
• 75326-15-7 (2-bromo-1-phenylethyl)dimethylsulphonium bromide 
• 100-42-5 styrene 
• 13686-33-4 t-butyl azide 
• 108-88-3 toluene 
• 6852-58-0 N-benzylidene tert-butylamine 
• 25628-09-5 tetramethylammonium trifluoromethanesulphonate 

Downstream Products

• 136912-55-5 [1-tert-Butyl-4-phenyl-3-p-tolyl-imidazolidin-(2Z)-ylidene]-p-tolyl-amine 
• 116780-50-8 (R)-1-tert-Butyl-3-phenylazetidin-2-one 
• 116780-49-5 (S)-1-tert-Butyl-3-phenylazetidin-2-one 
• 87451-13-6 (S)-1-tert-Butyl-3-phenylazetidin-2-one 
• 136912-54-4 [1-tert-Butyl-3,4-diphenyl-imidazolidin-(2Z)-ylidene]-phenyl-amine 
• 88000-32-2 (1,2-diphenylphosphirane)pentacarbonyltungsten 
• 109976-33-2 (CH₃)3CNCH(C₆H₅)CH₂P(C₆H₅)W(CO)5 
• 109976-34-3 (CH₃)3CNCH(C₆H₅)CH₂P(C₆H₅)W(CO)5 

Relevant academic research and scientific papers

A lithiomethyl trimethylammonium reagent as a methylene donor

Straightforward deprotonation of soluble tetramethylammonium salts with alkyllithium reagents gives lithiomethyl trimethylammonium reagents. Coordination of the Li cation is crucial to the stability of these 'N-C ylides'. These reagents were used to prepare epoxides, aziridines and allylic alcohols. This journal is the Partner Organisations 2014.

Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates

The dipyrrinato iron catalyst reacts with organic azides to generate a reactive, high-spin imido radical intermediate, distinct from nitrenoid or imido species commonly observed with low-spin transition metal complexes. The unique electronic structure of

Regioselective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines using Br- Ph3+PPEG 600P+Ph3Br- as an efficient, homogenous recyclable catalyst at ambient conditions

Polyethylene glycol functionalized phosphonium salt (Br- Ph 3+PPEG600P+Ph3Br -) was found to be an efficient, homogenous, recyclable catalyst for coupling of CO2 with a variety of aziridines producing corresponding 5-aryl-2-oxazolidinones with good yields and excellent regioselectivity under relatively mild and solvent free conditions. Furthermore, the catalyst was effectively recycled for four consecutive cycles without any significant loss in its catalytic activity and selectivity.

Polystyrene-supported amino acids as efficient catalyst for chemical fixation of carbon dioxide

Four new polystyrene-supported amino acids have been synthesized and applied to the chemical fixation of carbon dioxide for the first time. Two series of experiments with polystyrene-supported threonine (PS-Thr) and polystyrene-supported tyrosine (PS-Tyr) as catalyst, respectively, were conducted to study the effect of the reaction conditions on the carboxylation of propylene oxide/carbon dioxide. There was no considerable decrease in the yield of propylene carbonate after the polystyrene-supported amino acids were used five times, indicating that these catalysts are very stable. It was demonstrated that these catalysts were very efficient in the carboxylation of various epoxides and aziridines with carbon dioxide under mild conditions without any solvents. The mechanism for this carboxylation is also discussed.

Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions

A series of easily prepared Lewis basic ionic liquids were developed as recyclable and efficient catalysts for selective synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 without utilization of any organic solvent or additive. Notably, high conversion, chemo- and regio-selectivity were attained when 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane bromide ([C4DABCO]Br) was used as the catalyst. Furthermore, the catalyst could be recycled over four times without appreciable loss of catalytic activity. The effects of the catalyst structure and various reaction parameters on the catalytic performance were investigated in detail. This protocol was found to be applicable to a variety of aziridines producing the corresponding 5-aryl-2-oxazolidinones in good yields and excellent regioselectivities. Therefore, this solvent-free process thus represents an environmentally friendly process for ionic liquid-catalyzed conversion of CO2 into value-added chemicals. A possible catalytic cycle for CO2 activation induced by nucleophilic tertiary nitrogen of the ionic liquid was proposed, based on studies using in situ FT-IR spectroscopy under CO2 pressure.

Quaternary ammonium bromide functionalized polyethylene glycol: A highly efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions

(Chemical Equation Presented) A quaternary ammonium bromide covalently bound to polyethylene glycol (PEG, MW = 6000), i.e., PEG6000- (NBu3Br)2, was found to be an efficient and recyclable catalyst for the cycloaddition reaction of aziridines to CO2 under mild conditions without utilization of additional organic solvents or cocatalysts. As a result, 5-aryl-2-oxazolidinone was obtained in high yield with excellent regioselectivity. The catalyst worked well for a wide variety of 1-alkyl-2-arylaziridines. Besides, the catalyst could be recovered by centrifugation and reused without significant loss of catalytic activity and selectivity.

A MILD CYCLIZATION OF 2-AMINOALCOHOLS TO AZIRIDINES USING DIPHOSPHORUS TETRAIODIDE

The reaction of 2-aminoalcohols with diphosphorus tetraiodide in benzene at room temperature leads to the corresponding aziridines in good to moderate yields.

S-Ethenylsulfoximine Derivatives. Reagents for Ethylenation of Protic Nucleophiles

The preparation of S-vinyl and S-(2-substituted)ethenyl derivatives of sulfoximines is described.Vinyl-, (2-phenylethenyl)-, (2,2-diphenylethenyl)-, (2-methyl-1-propenyl)-, (dimethylamino)phenyloxosulfonium fluoroborates were found to undergo an addition-elimination reaction sequence with protic nitrogen and carbon nucleophiles, resulting in ethylenation of the nucleophile and N,N-dimethylbenzenesulfinamide.Primary amines gave aziridines, enamines gave cyclopropyl derivatives of iminium salts or pyrrolidinium salts, anions of active methylene compounds gave dihydrofurans and/or cyclopropanes, and anions of nitroalkanes gave cyclic nitronic esters and/or nitrocyclopropanes.In several cases vinyl salts were generated in situ from β-methoxyoxosulfonium salts.Treatment of (-)-(S)-dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate with methyl cyanoacetate in methanol containing sodium methoxide gave, in 81percent yield, (+)-(1S,2R)-methyl 1-cyano-2-phenylcyclopropanecarboxylate of 25.5percent optical purity.The same salt upon treatment with methyl nitroacetate gave, in 95percent yield, methyl 4-phenyl-3-isoxazolinecarboxylate 2-oxide with 33percent enantiomeric excess.Cyclopropanes were formed upon treatment of S-methyl-S-(trans-2-phenylethenyl)-N-(p-tolylsulfonyl)sulfoximine with anions of active methylene compounds.