33898-53-2

Basic information

• Product Name: aziridine-2-carbonitrile
• Synonyms: aziridine-2-carbonitrile;2,3-Iminopropionitrile;2-Cyanoaziridine;AZIRIDINE-2-CARBONITRILE(WXC05978)
• CAS NO: 33898-53-2
• Molecular Formula: C₃H₄N₂
• Molecular Weight: 68.07726
• EINECS: 251-725-6
• Mol File: 33898-53-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 183.7 °C at 760 mmHg
• Flash Point: 64.9 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 0.761mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: aziridine-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: aziridine-2-carbonitrile(33898-53-2)
• EPA Substance Registry System: aziridine-2-carbonitrile(33898-53-2)

Safety Data

• Hazardous Substances Data: 33898-53-2(Hazardous Substances Data)

Usage

General Description

Aziridine-2-carbonitrile is a chemical compound with the molecular formula C3H4N2. It is a highly reactive, heterocyclic compound that contains a three-membered ring with one nitrogen atom and two carbon atoms. Aziridine-2-carbonitrile is used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It is also used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-nitrogen bonds. Due to its high reactivity, aziridine-2-carbonitrile should be handled with caution and proper safety measures to avoid potential hazards.

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

Upstream product

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

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 articles and documents

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.

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 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.