4164-25-4

Usage

Physical state

Colorless liquid

Odor

Pleasant

Primary use

Intermediate in the production of pharmaceuticals and agrochemicals

Other uses

Ligand in organic synthesis, chiral auxiliary in asymmetric synthesis

Toxicity

Low acute toxicity

Environmental impact

Low potential

Handling precautions

May cause irritation to skin, eyes, and respiratory system upon exposure

Upstream product

• 100-52-7 benzaldehyde 
• 74-88-4 methyl iodide 
• 74-89-5 methylamine 
• 100-42-5 styrene 
• 36378-98-0 S-(dimethylamino)-S-phenyl(trans-2-phenyleth-1-enyl)oxosulfonium fluoroborate 
• 75326-15-7 (2-bromo-1-phenylethyl)dimethylsulphonium bromide 
• 1630-62-2 3-methyl-2-phenyl-oxazolidine 

Downstream Products

• 58777-98-3 1,1-dimethyl-2-phenylaziridinium fluorosulfonate 
• 864347-90-0 [2-(1-methylaziridin-2-yl)phenyl]-phenyl-methanol 
• 20805-26-9 3-methyl-5-phenyloxazolidin-2-one 
• 291533-24-9 (R)-3-methyl-4-phenyl-1,3-oxazolidine-2-one 
• 1361410-57-2 2,5-diphenyl-1,4-dimethylpiperazine 
• 1361410-93-6 C₁₂H₁₅N 

Relevant academic research and scientific papers

Interaction of Nitric Oxide with Paramagnetic and Diamagnetic Alkyls of Titanium, Zirconium, Vanadium, Niobium, and Tantalum

An earlier observation that there is a profound difference in the way paramagnetic and diamagnetic alkyl compounds of transition metals react with nitric oxide is extended.The reaction of NO with bis(η5-cyclopentadienyl)-dimethylniobium(IV), d1, can be followed by nuclear magnetic resonance spectra and intermediates detected.The final product of the reaction is bis(η5-cyclopentadienyl)methyloxoniobium(V), which with excess of NO, gives the N-methyl-N-nitrosohydroxylaminato-complex Nb(η-C5H5)2(O).An intermediate niobioaziridine collapses with methylnitrene transfer to give azomethane, and in the presence of styrene, an aziridine.Tetrakis(trimethylsilylmethyl)vanadium(IV) gives with NO the previously known VO(CH2SiMe3)3 while the titanium(III), d1, compounds Ti(η-C5H5)2R (R = Ph or CH2Ph) lose both cyclopentadienyl and aryl or benzyl groups to give trimeric species Ti3(η-C5H5)3O4(NO) that has oxo-bridges and a bent Ti-NO group.The diamagnetic alkyls of titanium and zirconium, TiR4, TiR3Cl, TiR2Cl2, ZrR4, and ZrR2Cl2 (R = CH2SiMe3 or CH2CMe3) and NO give N-alkyl-N-nitrosohydroxylaminato-complexes.The titanium compounds are six-co-ordinate with unidentate and bidentate ON(R)NO groups, while the zirconium compounds are eight-co-ordinate with chelate groups only.The pentamethyls MMe5 (M = Nb or Ta) and NO give NbMe23 and 2>2 respectively.

Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide

The catalytic potential of ammonium halide salts was explored in the coupling reaction of a model aziridine with carbon dioxide, highlighting the superior activity of [NH2Et2]I. Then, working at room temperature, atmospheric CO2 pressure and in the absenc

A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution

A facile microwave assisted three-component protocol allows the synthesis of chiral aryl-1,2-mercaptoamines in water in a few minutes with high yields, bypassing the use of toxic aziridine intermediates. The chiral 1,2-mercaptoamines were then deracemized through enzymatic resolution of the racemates using monoamine oxidase (MAO-N) biocatalysts.

Styrene Aziridination by Iron(IV) Nitrides

Thermolysis of the iron(IV) nitride complex [PhB(tBuIm)3FeN] with styrene leads to formation of the high-spin iron(II) aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)]. Similar aziridination occurs with both electron-rich and electron-poor styrenes, while bulky styrenes hinder the reaction. The aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)] acts as a nitride synthon, reacting with electron-poor styrenes to generate their corresponding aziridino complexes, that is, aziridine cross-metathesis. Reaction of [PhB(tBuIm)3Fe-N(CH2CHPh)] with Me3SiCl releases the N-functionalized aziridine Me3SiN(CH2CHPh) while simultaneously generating [PhB(tBuIm)3FeCl]. This closes a synthetic cycle for styrene azirdination by a nitride complex. While the less hindered iron(IV) nitride complex [PhB(MesIm)3FeN] reacts with styrenes below room temperature, only bulky styrenes lead to tractable aziridino products.

Proline-catalyzed synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions

Natural a-amino acids were proven to be ecofriendly and recyclable catalysts for the carboxylation of aziridines with CO2 without utilization of any organic solvents or additives. Notably, a series of 5-aryl-2-oxazolidinones were obtained in go

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.

Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide

A simple approach for facile synthesis of 5-aryl-2-oxazolidinones in excellent regioselectivity from aziridines under compressed CO2 conditions was developed in the absence of any catalyst and organic solvent. The reaction outcome was found to be tuned by subtly adjusting CO2 pressure. The adduct formed in situ of aziridine and CO2 is assumed to act as a catalyst in this reaction, which was also studied by means of in situ FT-IR technique.

METHOD FOR SYNTHESIZING AN N-UNSUBSTITUTED OR N-SUBSTITUTED AZIRIDINE

Process for preparing an N-unsubstituted or N-substituted aziridine of the formula which comprises reacting an olefin of the formula I where R1 to R5 are each, independently of one another, hydrogen, a linear or branched alkyl radica