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

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

Uses

Used in Organic Synthesis:
2-azidoethanamine is used as a reagent in organic synthesis for the production of various organic chemicals. Its high reactivity allows it to participate in a range of chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used as a Precursor:
In the chemical industry, 2-azidoethanamine is used as a precursor for the production of other organic chemicals. Its ability to undergo various chemical transformations makes it a useful starting material for creating a wide array of compounds with diverse applications.
Used in Specialized Industrial Processes:
Due to its instability and hazardous nature, 2-azidoethanamine is primarily used in specialized industrial processes that require strict safety protocols. These processes often involve controlled environments and specific handling procedures to mitigate the risks associated with its use.

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

Upstream product

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

Downstream Products

• 107-15-3 ethylenediamine 
• 72200-26-1 N-(2-azido-ethyl)-benzamide 
• 261912-63-4 N-(2-azidoethyl)-4-methylbenzenesulfonamide 
• 912849-66-2 (4R)-N-(3-((2-azidoethyl)amino)-3-oxopropyl)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamide 
• 1178886-40-2 C₁₁H₁₄N₄O₂S 
• 1192358-21-6 N-(2-azidoethyl)-4-hexylbenzamide 
• 1192358-18-1 N-(2-azidoethyl)-2,4,6-trichlorobenzamide 
• 1192358-17-0 N-(2-azidoethyl)-3,5-difluorobenzamide 
• 1192358-11-4 N-(2-azidoethyl)cinnamamide 
• 1192358-10-3 N-(2-azidoethyl)benzenesulfonamide 
• 1192358-15-8 N-(2-azidoethyl)-2-iodobenzamide 
• 1192358-16-9 N-(2-azidoethyl)-4-tert-butylbenzamide 
• 1192358-28-3 (E)-N-(2-azidoethyl)-2-methyl-3-phenylacrylamide 
• 1192358-12-5 N-(2-azidoethyl)-2-(phenylthio)acetamide 

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.

Site-directed attachment of photoexcitable spin labels for light-induced pulsed dipolar spectroscopy

Photoexcited triplet states are gaining popularity as spin labels in pulsed electron paramagnetic resonance (EPR) spectroscopy. Here, we demonstrate that the fluorophores Eosin Y, Rose Bengal and Atto Thio12 are suitable markers for distance determination

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.

Creation of Customized Bioactivity within a 14-Membered Macrolide Scaffold: Design, Synthesis, and Biological Evaluation Using a Family-18 Chitinase

Argifin, a 17-membered pentapeptide, inhibits chitinase. As argifin has properties that render it unsuitable as a drug development candidate, we devised a mechanism to create the structural component of argifin that bestows the chitinase inhibition and introduce it into a 14-membered macrolide scaffold. Here we describe (1) the designed macrolide, which exhibits ～200-fold more potent chitinase inhibition than argifin, (2) the binding modes of the macrolide with Serratia marcescens chitinase B, and (3) the computed analysis explaining the reason for derivatives displaying increased inhibition compared to argifin, the macrolide aglycone displaying inhibition in a nanomolar range. This promises a class of chitinase inhibitors with novel skeletons, providing innovative insight for drug design and the use of macrolides as adaptable, flexible templates for use in drug discovery research and development.

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.

Interface immobilization chemistry of cRGD-based peptides regulates integrin mediated cell adhesion

The interaction of specific surface receptors of the integrin family with different extracellular matrix-based ligands is of utmost importance for the cellular adhesion process. A ligand consists of an integrin-binding group, here cyclic RGDfX, a spacer molecule that lifts the integrin-binding group from the surface and a surface anchoring group. c(-RGDfX-) peptides are bound to gold nanoparticle structured surfaces via polyproline, polyethylene glycol or aminohexanoic acid containing spacers of different lengths. Although keeping the integrin-binding c(-RGDfX-) peptides constant for all compounds, changes of the ligand's spacer chemistry and length reveal significant differences in cell adhesion activation and focal adhesion formation. Polyproline-based peptides demonstrate improved cell adhesion kinetics and focal adhesion formation compared with common aminohexanoic acid or polyethylene glycol spacers. Binding activity can additionally be improved by applying ligands with two head groups, inducing a multimeric effect. This study gives insights into spacer-based differences in integrin-driven cell adhesion processes and remarkably highlights the polyproline-based spacers as suitable ligand-presenting templates for surface functionalization. Self-organized spatial positioning of cRGD patches on glass via a gold nanopattern as a biomimetic approach to engineer cellular environments. Regulation of integrin-mediated cellular responses is achieved by tuning the length and chemical nature of the cRGD-presenting molecule. Fibroblasts exhibit higher affinity towards surfaces coated with cRGD containing a polyproline spacer compared with alkane- and polyethylene glycol-based spacers.

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.

Amino-functionalized single-chain bolalipids: Synthesis and aggregation behavior of new basic building blocks

Herein, we report the synthesis of two novel, amino-functionalized single-chain bolalipids and, based on those, a general synthetic approach for the insertion of various carboxylic acids into the bolalipid headgroups, e.g. α-lipoic acid for one-dimensional fixation of gold nanoparticles, sorbic acid for polymerization experiments, or lysine for the use in gene delivery systems. The temperature- and pH-dependent self-assembly of amino-functionalized bolalipids into nanofibers and micelles was investigated by differential scanning calorimetry (DSC), transmission electron microscopy (TEM) and dynamic light scattering (DLS). Rheological measurements were used to describe the macroscopic behavior of the formed temperature switchable hydrogels that can be fine-tuned for drug delivery applications. We showed that the viscoelastic properties of the hydrogel strongly depend on ionic interactions between bolalipid headgroups as well as on the ability to form hydrogen bonds.

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.

A general method for functionalisation of microgel particles with primary amines using click chemistry

In this study we introduce a general method for functionalising microgel particles with primary amine groups using a one-step copper catalysed azide-alkyne cycloaddition (CuAAC) reaction. Three different families of microgels containing copolymerised propargyl acrylate (PA) were prepared and then reacted with 2-azido-1-ethylamine (AEA) using CuAAC. The microgels contained poly(ethyl acrylate) (PEA), poly(2-vinylpyridine) (PVP) or poly(N-isopropylacrylamide) (PNP). The functionalisation of the microgels containing PA (i.e., PX-PA) by AEA to give primary amine functionalised particles (PX-PA-AEA) was assessed by elemental analysis and FTIR. The reaction of AEA with PA was quantitative for each of the PX-PA-AEA microgels (X = EA, VP and NP). The PX-PA-AEA systems generally showed larger pH-triggered swelling and zeta potentials than the non-clicked PX-PA particles. The results also showed that PA restricted swelling of the PX-PA and PX-PA-AEA particles by acting as a crosslinker. Of the three microgel systems studied, PVP-PA-AEA had the best combination of high AEA incorporation and pH-triggered swelling.