2H-Azirine

Base Information

• Chemical Name: 2H-Azirine
• CAS No.: 157-16-4
• Molecular Formula: C2H3 N
• Molecular Weight: 41.0525
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60166176
• Nikkaji Number: J2.956.012I,J79.464C
• Wikidata: Q424273
• Metabolomics Workbench ID: 54300
• Mol file: 157-16-4.mol

Synonyms:2H-Azirine;2H-azirene;157-16-4;3h-azirine;CHEBI:30971;(Aziridine-1,2-diyl)radical;DTXSID60166176;Q424273

Chemical Property of 2H-Azirine

Chemical Property:

• Vapor Pressure: 1030mmHg at 25°C
• Boiling Point: 16.3°Cat760mmHg
• Flash Point: °C
• PSA: 12.36000
• Density: 1.03g/cm³
• LogP: -0.49360
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 41.026549100
• Heavy Atom Count: 3
• Complexity: 29.8

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=N1

Technology Process of 2H-Azirine

There total 7 articles about 2H-Azirine 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: 36.0%

azide vinylique (7570-25-4) → Δ1-azirine (157-16-4) + methyl isocyanate (593-75-9,685498-28-6) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

at 500 ℃; under 0.001 Torr; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)86146-9

Reference yield:

azide vinylique (7570-25-4) → Δ1-azirine (157-16-4) + methyl isocyanate (593-75-9,685498-28-6) + 1-ethyleneimine (17619-22-6) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

at 800 ℃;

Reference yield:

1,2,3-triazole (288-36-8) → Δ1-azirine (157-16-4) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

at 596.9 ℃; under 0.008 Torr; Product distribution; also at 970 K, effect of the presence of Cu₂O (at 515 - 550 K);

DOI:10.1021/ja00364a037

upstream raw materials:

methylene

hydrogen cyanide

azide vinylique

1,2,3-triazole

Refernces

Novel diaryl-2H-azirines: Antitumor hybrids for dual-targeting tubulin and DNA

10.1016/j.ejmech.2021.113256

The study presents the design and synthesis of a novel class of diaryl-substituted 2H-azirines, which are hybrid antitumor agents targeting both tubulin and DNA. These compounds were developed by combining pharmacophores from Combretastatin A-4 (CA-4), a known tubulin polymerization inhibitor, and aziridine-type alkylating agents, which are DNA damaging agents. The primary aim was to evaluate the antitumor activities of these compounds in vitro against various cancer cell lines and to investigate their mechanism of action. The most potent compound, 6h, showed significant activity against four cancer cell lines with low IC50 values and demonstrated dual-targeting capabilities in mechanistic studies. It inhibited tubulin polymerization, induced DNA damage, triggered cellular apoptosis, and showed anti-angiogenic effects. The study also included in vivo testing in a nude mice xenograft model, where 6h significantly inhibited tumor growth with low toxicity, indicating its potential for further development as a novel cancer therapy with a unique mechanism of action.