87156-40-9

Basic information

• Product Name: 2-azidoethanamine
• Synonyms: 2-azidoethanamine;2-Azidoethylamine [2-Azidoethanamine];2-Azidoethylamine [2-Azidoethamine]
• CAS NO: 87156-40-9
• Molecular Formula: C₂H₆N₄
• Molecular Weight: 86.0958
• Mol File: 87156-40-9.mol
• Article Data: 81

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 2-azidoethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azidoethanamine(87156-40-9)
• EPA Substance Registry System: 2-azidoethanamine(87156-40-9)

Safety Data

• Hazardous Substances Data: 87156-40-9(Hazardous Substances Data)

Usage

General Description

2-azidoethanamine, also known as ethylenimine azide, is a chemical compound with the molecular formula C2H5N3. It is a highly reactive and unstable compound that is used in organic synthesis and as a precursor for the production of other organic chemicals. 2-azidoethanamine is a colorless liquid at room temperature and is highly toxic, with potential mutagenic and carcinogenic properties. It is also considered a potential explosive and must be handled with extreme caution. Due to its instability and hazardous nature, the use and handling of 2-azidoethanamine are highly regulated, and it is primarily used in specialized industrial processes under strict safety protocols.

InChI:InChI=1/C2H6N4/c3-1-2-5-6-4/h1-3H2

Upstream product

• 107-09-5 2-bromoethylamine 
• 39684-80-5 2-(tert-butoxycarbonylamino)ethyl bromide 
• 58861-74-8 2-bromoethylamine hydrochloride 
• 19263-22-0 1-azido-2-bromoethane 
• 870-24-6 2-chloroethanamine hydrochloride 
• 117861-38-8 tert-butyl 2-azidoethylcarbamate 
• 689-98-5 chloroethylamine 
• 861579-34-2 (2-azido-ethyl)-carbamic acid ethyl ester 
• 2576-47-8 2-bromoethylamine hydrobromide 

Downstream Products

• 261912-63-4 N-(2-azidoethyl)-4-methylbenzenesulfonamide 
• 107-15-3 ethylenediamine 
• 1178886-40-2 C₁₁H₁₄N₄O₂S 
• 1224434-31-4 N-((1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-methoxyphenyl)diazenecarboxamide 
• 1224434-32-5 N-((1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-nitrophenyl)diazenecarboxamide 
• 1224434-27-8 N-((1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl)methyl)-2-phenyldiazenecarboxamide 
• 1224434-28-9 N-((1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl)methyl)-2-p-tolyldiazenecarboxamide 
• 1224434-29-0 N-([1-(2-aminoethyl)-4-phenyl-1H-1,2,3-triazol-4-yl]methyl)-2-(4-chlorophenyl)diazenecarboxamide 
• 1224434-30-3 N-((1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-(trifluoromethyl)phenyl)diazenecarboxamide 
• 1224434-33-6 N-((1-(3-aminopropyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-(trifluoromethyl)phenyl)diazenecarboxamide 
• 1224434-34-7 N-((1-(4-aminobutyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-(trifluoromethyl)phenyl)diazenecarboxamide 
• 1224434-35-8 N-((1-(5-aminopentyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-(trifluoromethyl)phenyl)diazenecarboxamide 
• 1101852-29-2 2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-amine 
• 1498411-23-6 C₂₁H₂₃N₁₁O₅ 

Relevant articles and documents

Signal amplification and transduction by photo-activated catalysis

A simple flavin-based catalytic system is able to transform light into chemical output with amplified response utilizing a Cu(i)-catalyzed cycloaddition reaction. The Royal Society of Chemistry.

Anthranilic Acid as a Versatile Fluorescent Tag and Linker for Functional Glycomics

The advancement of glycoscience is critically dependent on the access to a large number of glycans for their functional study. Naturally occurring glycans are considered a viable source for diverse and biologically relevant glycan libraries. A mixture of free reducing glycans released from natural sources can be fluorescently tagged and separated by chromatography to produce a natural glycan library. Anthranilic acid (AA) has been widely used to fluorescently tag reducing glycans for HPLC or LC/MS analysis. However, AA conjugated glycans are not efficiently immobilized on microarray slides due to the lack of a primary alkylamine functional group. In this study, we have developed simple and efficient chemistry for bioconjugation and further functionalization of glycan-AA conjugates. This new approach enables quick preparation of glycan microarrays and neoglycoproteins from glycan-AA conjugates, which can be separated by weak anion exchange (WAX) and C18 reversed-phase HPLC.

Novel thermoresponsive polymers tunable by pH

Thermoresponsive polymers that are pH tunable were successfully synthesized by a combination of atom transfer radical polymerization (ATRP) and Cu(I)-catalyzed 1,3-dipolar cycloaddition of azide and alkynes (click chemistry). ATRP was employed to synthesize poly(2-hydroxyethyl methacrylate) (PHEMA), followed by introduction of alkyne groups using pentynoic acid, leading to PHEMA-alkyne. 2-Azidoethylamine, 2-azido-N,N-dimethylethylamine, and 2-azido-N,N-diethylethylamine were added to the PHEMA-alkyne backbone via click chemistry. Molecular weight, molecular weight distribution, and click reaction efficiency were determined by gel permeation chromatography (GPC) and 1H NMR spectroscopy. The average molecular weight (Mn) of the resulting polymers ranged from 5.6 ×104 to 7.0 ×104 depending on the molecular architecture. The molecular weight distribution was low (Mn/Mn = 1.25-1.35). The transmission spectra of the 0.1 wt % aqueous solutions of the resulting polymers with different pH values at 650 nm were measured as a function of temperature. Results showed that the lower critical solution temperature (LCST) could be dramatically affected by solution pH. To give additional evidence for pH-responsive thermal transition, in-situ temperature-dependent 1H NMR measurements in deuterated water (0.01 wt %) were conducted. The LCST values measured by in-situ 1H NMR correlated well with those determined by turbidimetry.

Biological evaluation of avidin-based tumor pretargeting with DOTA-Triazole-Biotin constructed via versatile Cu(I) catalyzed click chemistry

Background: The biotin-avidin interaction remains a gold standard for the two-step pretargeting approach to image tumor sites. We aim to develop two-step pretargeting systems utilizing 99mTc labeled biotin functionalized macrocyclic chelating agents synthesized using the highly efficient Cu(I) catalyzed azide-alkyne cycloaddition for potential radioimaging applications. Methods: A facile synthesis of DOTA-Triazole-Biotin, radiocomplexation with 99mTc and the pretargeting protocol is described. The synthesis features Cu(I) catalyzed click conjugation between biotinylated azide and propynyl functionalized DO3A. 99mTc radiolabeling was performed to detect the accumulation of avidin as the pretargeting agent. Cytotoxicity was determined using the trypan blue exclusion assay, macrocolony, and MTT assay. Cell uptake studies were performed using radiolabeled DOTA-Triazole-Biotin and compared with avidin treated cells for 2 h. Tumor imaging was performed in U-87MG cell line implanted tumor bearing nude mice and uptake of the radiotracer was estimated. Results: All compounds have been successfully characterized by NMR and MS spectroscopy. More than 96% radiolabeling efficiency was obtained and the radioconjugate exhibited sufficient stability under physiological conditions. Conclusion: To summarize, a new candidate for avidin based two-step pretargeting of tumors has been synthesized and evaluated for potential imaging and diagnostic applications. The chelate possesses high stability under physiological conditions, exhibits effective interaction with its avidin target, and low nonspecific retention in vivo.

Enhanced osteogenic differentiation of MC3T3-E1 on rhBMP-2-immobilized titanium via click reaction

In the present study, we report about the efficacy of titanium surface-immobilized with bone morphogenetic protein-2 (BMP-2) via click reaction on enhanced osteogenic differentiation of MC3T3-E1 cells. The surface was characterized by static contact angles and XPS measurements, which indicated that pristine titanium (Ti-1) was successfully surface-modified via click chemistry (aminated titanium, Ti-4). By quantitative analysis of heparin immobilized on aminated titanium (Ti-4), we found that the Ti-4 can be used as a good candidate to immobilize biomolecules such as heparin. BMP-2 from titanium immobilized with BMP-2 (Ti-6) was released for a period of 28 days in a sustained manner. The highest proliferation rate of MC3T3-E1 cells was observed on Ti-6. Through in vitro tests including alkaline phosphatase (ALP) activity, calcium deposition and real-time polymerase chain reaction (real-time PCR), we found that Ti-6 can be used as a good implant to enhance the osteogenic differentiation of MC3T3-E1 cells.

Surfactant-free one-step synthesis of dual-functional polyurea microcapsules: Contact infection control and drug delivery

Surface functionalized polyurea microcapsules (MCQ) are synthesized in one step. Dimethyl-dodecyl-(5-hydroxy-pentyl)-ammonium bromide (DAB), a hydroxyl-end-capped quaternary ammonium salt, is synthesized and adopted as a new surfmer for the synthesis of M

Novel menadione hybrids: Synthesis, anticancer activity, and cell-based studies

A series of novel menadione-based triazole hybrids were designed and synthesized by employing copper-catalyzed azide-alkyne cycloaddition (CuAAC). All the synthesized hybrids were characterized by their spectral data (1H NMR, 13C NMR, IR, and HRMS). The synthesized compounds were evaluated for their anticancer activity against five selected cancer cell lines including lung (A549), prostate (DU-145), cervical (Hela), breast (MCF-7), and mouse melanoma (B-16) using MTT assay. The screening results showed that majority of the synthesized compounds displayed significant anticancer activity. Among the tested compounds, the triazoles 5 and 6 exhibited potent activity against all cell lines. In particular, compound 6 showed higher potency than the standard tamoxifen and parent menadione against MCF-7 cell line. Flow cytometric analysis revealed that compound 6 arrested cell cycle at G0/G1 phase and induced apoptotic cell death which was further confirmed by Hoechst staining, measurement of mitochondrial membrane potential (ΔΨm) and Annexin-V-FITC assay. Thus, compound 6 can be considered as lead molecule for further development as potent anticancer therapeutic agent.

Template synthesis of tungsten complexes with saturated N-heterocyclic carbene ligands

Tungsten complex 5 with a coordinated 2-azidoethyl isocyanide ligand reacts with PMe3 at the azido function to give a complex with a coordinated iminophosphorane which upon hydrolysis of the P=N bond yields a complex with an NH,NH-stabilized N-heterocyclic carbene ligand, 7; alkylation of the carbene ring nitrogen atoms gives a complex with an N,N′-dialkylated imidazolidin-2-ylidene ligand, 8. The Royal Society of Chemistry 2005.

Structure determination of bis{(4Z)-1-(2-azidoethyl)-4-[(pyridin-2-yl) methylidene]-2-thiolatoimidazol-5(4H)-one}dicopper chloride from X-ray powder diffraction data

The new tridentate organic N2S-type ligand, (4Z)-1-(2- azidoethyl)-4-[(pyridin-2-yl)-methylidene]-2-thioxoimidazol-5(4H)-one (LH), was synthesized. The reaction of LH with copper(II) chloride in a CH 2Cl2/MeOH mixture afforded the coordination compound of the composition L2Cu2Cl (3). The crystal structure of 3 was solved and refined from X-ray powder diffraction data. Complex 3 has a binuclear structure with a short interatomic Cu-Cu distance and one bridging chlorine atom, which is located almost symmetrically with respect to both metal atoms. The planar organic ligands are noncoplanar and are at an angle of 53.56(1) to each other.

Bivalent Approach for Homodimeric Estradiol Based Ligand: Synthesis and Evaluation for Targeted Theranosis of ER(+) Breast Carcinomas

The synthesis of estradiol based bivalent ligand [(EST)2DT] is reported and its potential for targeted imaging and therapy of ER(+) tumors has been evaluated. For the purpose, ethinylestradiol was functionalized with an azidoethylamine moiety via click chemistry. The resultant derivative was reacted in a bivalent mode with DTPA-dianhydride to form the multicoordinate chelating agent, (EST)2DT which displayed capability to bind 99mTc. The radiolabeled complex, 99mTc-(EST)2DT was obtained in >99% radiochemical purity and 20-48 GBq/μmol of specific activity. RBA assay revealed ～15% binding with estrogen receptor. Evaluation of ligand on ER(+)-cell line (MCF-7) suggested enhanced and ER-mediated uptake. In vivo assays displayed early tracer accumulation in MCF-7 xenografts with tumor to muscle ratio ～6 in 2 h and negligible uptakes in nontargeted organs. MTT assay performed on ER(+) and ER(-) cell lines displayed selective inhibition of ER(+) cancer cell growth with IC50 = 14.3 μM which was comparable to tamoxifen. The anticancer activity of the ligand is possibly due to the increase in ERβ and suppression of ERα protein levels in gene transcription. The studies reveal the potential of (EST)2DT as diagnostic imaging agent with the additional benefits in therapy. (Chemical Equation Presented).

Novel diphenylmethyl compounds having mycobacterium tuberculosis inhibitory activity

The invention relates to novel diphenylmethyl derivatives having mycobacterium tuberculosis inhibitory activity and a preparation method thereof and particularly relates novel diphenylmethyl derivatives having activity for inhibiting replicative and non-replicating mycobacterium tuberculosis and a preparation method thereof. In particular, the invention relates to compounds shown in the formula (I) or all possible isomers, prodrugs, pharmaceutically acceptable salts, solvates or hydrates thereof, wherein the variables are as described in the specification. The invention also relates to the preparation method of the compounds and their pharmaceutical compositions and a use of the compounds in preparation of drugs for treating mycobacterium tuberculosis infection-caused diseases.

Method for synthesizing C15 urushiol-based triazole derivatives

The invention relates to a method for introducing a triazole structure into C15 urushiol-based ether according to a group superposing principle with C15 triene urushiol (3-((8Z,11E,13Z)-pentadeca-8,11,13-trien-1-yl)benzene-1,2-diol) or C15 monoene urushiol ((Z)-3-(pentadec-8-en-1-yl) benzene-1,2-diol) in traditional raw lacquer urushiol in the East Asian Region as a raw material. C15 urushiol-based triazole derivatives can significantly reduce or even eliminate the sensitization of the C15 triene urushiol, and can inhibit the proliferation of liver cancer cells to achieve the attenuation and synergism effects; and the method enlarges the medical application field of the C15 tris(mono)ene urushiol.