33898-53-2

Usage

Uses

Used in Pharmaceutical Industry:
Aziridine-2-carbonitrile is utilized as a key building block for the synthesis of various pharmaceuticals. Its unique structure and reactivity allow for the creation of a wide range of biologically active compounds, contributing to the development of new medications and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, aziridine-2-carbonitrile serves as a vital component in the production of pesticides and other crop protection agents. Its incorporation into these products enhances their effectiveness in protecting crops from pests and diseases, thereby supporting agricultural productivity.
Used in Organic Synthesis:
Aziridine-2-carbonitrile is employed as a reagent in organic synthesis, particularly for the formation of carbon-carbon and carbon-nitrogen bonds. Its high reactivity makes it a valuable tool in the creation of complex organic molecules, which are essential in various chemical and industrial applications.
Safety Considerations:
Due to the high reactivity of aziridine-2-carbonitrile, it is crucial to handle aziridine-2-carbonitrile with caution. Proper safety measures, including the use of personal protective equipment and adherence to safety protocols, are necessary to prevent potential hazards and ensure the safe conduct of experiments and industrial processes involving this chemical.

InChI:InChI=1/C3H4N2/c4-1-3-2-5-3/h3,5H,2H2

Upstream product

• 157-17-5 azirene 
• 74-90-8 hydrogen cyanide 
• 4554-16-9 2,3-dibromopropionitrile 
• 69245-10-9 2-aminoprop-2-enenitrile 

Downstream Products

• 130780-94-8 (±)-N-Boc-2-amino-2-hydroxymethylacetonitrile 
• 130780-96-0 rac-3-(2-Cyanoaziridin-1-yl)alaninnitril 
• 130780-95-9 rac-O³-Dibenzyloxyphosphorylserinnitril 
• 1750-09-0 N-Benzoylaziridin-2-carbonitril 
• 130780-92-6 rac-O³-Tosylserinenitril-hydrotosylat 
• 75985-58-9 1-(2-cyanoethyl)aziridine-2-carboxylic acid nitrile 
• 67413-30-3 (S)-Aziridin-2-carbonsaeureamid 
• 593-75-9 methyl isocyanate 
• 59264-17-4 N-(methylimino)acetonitrile 
• 75-05-8 acetonitrile 
• 628-87-5 iminodiacetonitrile 
• 110-61-2 butanedinitrile 
• 19866-98-9 (E/Z)-3-aminoprop-2-enenitrile 
• 55275-64-4 2-cyano-aziridine-1-carboxylic acid anilide 

Relevant academic research and scientific papers

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

Novel antitumor 2-cyanoaziridine-1-carboxamides

A set of 20 2-cyanoaziridine-1-carboxamides was synthesized from 2- cyanoaziridine and appropriate isocyanates. These compounds were active against a variety of solid and hematological tumor cells in culture, including strains resistant to doxorubicin and mitoxantrone. Their potencies in these assays correlated with the lipophilicity of substituents. The N- phenyl derivative was more potent and equally effective to imexon, a cyclized 2-cyanoaziridine-1-carboxamide of clinical interest, against cloned fresh human tumors.

Chemistry of aziridinecarboxylic acids; Part 2. Convenient synthesis of 2-aminopropenenitrile

2-Aminopropenenitrile (4) has been prepared by dehydrochlorination of 2-amino-3-chloropropanenitrile (3) with triethylamine. A simple and efficient synthesis of 2-cyanoaziridine (2) by reaction of 2,3-dibromopropanenitrile (1) with ammonia in methanol in the presence of triethanolamine is described.

Chemistry of alpha-aminonitriles. Aziridine-2-carbonitrile: photochemical formation from 2-aminopropenenitrile

2-Aminopropenenitrile in solvents such as MeCN, MeOH, or H2O is photoisomerized by UV light to racemic aziridine-2-carbonitrile (rac-2); the larger part of the starting material, however, fragments to HCN and MeCN. The observed photocyclization constitutes a structural connection within an ensemble of C3H4N2 compounds considered to be potentially relevant to prebiotic chemistry.

Chemistry of α-Aminonitriles. Aziridin-2-carbonitrile, a Source of Racemic O3-Phosphonoserinenitrile and Glycolaldehyde Phosphate

Racemic aziridine-2-carbonitrile (rac-1) in MeCN solution reacts regioselectively (>90percent) with 2 equiv. of TsOH at room temperature to form the hydrotosylate of racemic O3-tosylserinenitrile (rac-2) via a β-ring opening (Scheme 2).A similar regioselective reaction takes place between rac-1 and H3PO4 to produce racemic O3-phosphoserinenitrile (rac-3) which is in turn a source of glycolaldehyde phosphate (=formylmethyl dihydrogenphosphate) under the conditions of a 'retro-Strecker' reaction in aqueous solution (Scheme 6).These experiments document a close structural relationship between the simplest of the sugar phosphates and an α-aminonitrile precursor.

2-Cyanoaziridinyl-(1)-2-substituted-aziridinyl-(1)-methanes

A 2-cyanoaziridinyl-(1)-2-substituted-aziridinyl-(1)-methane STR1 wherein R is a nitrile or carbamoyl group, and R1 and R2 each independently is a hydrogen atom, an aliphatic hydrocarbon radical containing up to 10 carbon atoms optionally substituted by hydroxyl, alkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, cyano, 1, 2 or 3 halogens, cycloalkyl, phenyl or phenoxy; nitrile, carboxyl, alkoxycarbonyl or optionally hydrogenated monocyclic heteroaryl or phenyl optionally substituted by alkyl, alkoxy, hydroxy, alkoxcarbonyl, dialkylamino, alkylthio, trifluoromethyl, nitro, carbamoyl, nitrile, sulphonamido, hydroxyalkyl, methylenedioxy, or halogen; or R1 and R2, together with the carbon atom to which they are attached, form a ring containing up to 8 ring members of which at least one may be oxygen, sulphur, SO, SO2 NH, N-alkyl, N-acyl or N-alkoxycarbonylalkyl, and which can be substituted by alkyl, alkoxy, hydroxyl, alkylenedioxy, alkoxycarbonyl, hydroxyalkyl, alkoxycarbonylalkyl, dialkylamino, oxo or 2-cyanoaziridino groups, or can be fused to 1 or 2 benzene rings or can be bridged by alkylene radicals containing up to 3 carbon atoms. The compounds are characterized by cytostatic and immune response-stimulating activity.

Immune-stimulating and cancerostatic 1-acyl-2-cyanoaziridines

1-Acyl-2-cyanoaziridines of the formula STR1 wherein R is an acyl radical of a carboxylic, sulphonic, sulphinic, sulphenic, phosphonic or phosphoric acid, exhibit immune-stimulating and cancerostatic activities.