14860-64-1

Basic information

• Product Name: 4-azidoaniline
• Synonyms: 4-azidoaniline;4-Azidobenzenamine;Einecs 238-929-0
• CAS NO: 14860-64-1
• Molecular Formula: C₆H₆N₄
• Molecular Weight: 134.13864
• EINECS: 238-929-0
• Mol File: 14860-64-1.mol
• Article Data: 32

Chemical Properties

• Melting Point: 65-66 °C
• Appearance: /
• CAS DataBase Reference: 4-azidoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-azidoaniline(14860-64-1)
• EPA Substance Registry System: 4-azidoaniline(14860-64-1)

Safety Data

• Hazardous Substances Data: 14860-64-1(Hazardous Substances Data)

Usage

General Description

4-azidoaniline is an organic compound with the chemical formula C6H6N4. It is a derivative of aniline, with an azido group attached to the benzene ring. 4-azidoaniline is a pale yellow solid that is primarily used as a precursor in the synthesis of various organic compounds, including dyes and pharmaceuticals. It is also used in the production of polymers, and as a reagent in organic synthesis. 4-azidoaniline is considered to be a hazardous substance, as it can react violently with reducing agents and may cause irritation to the skin, eyes, and respiratory system upon exposure. Due to its azido group, which is highly reactive, it is important to handle and store 4-azidoaniline with caution and in accordance with proper safety protocols.

InChI:InChI=1/C6H6N4/c7-5-1-3-6(4-2-5)9-10-8/h1-4H,7H2

Upstream product

• 696-62-8 para-iodoanisole 
• 540-37-4 p-aminoiodobenzene 
• 1516-60-5 4-nitrophenyl azide 
• 1059625-65-8 4-aminobenzenediazonium 4-methylbenzenesulfonate 
• 106-40-1 4-bromo-aniline 
• 2294-47-5 1,4-diazidobenzene 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 103-92-4 4'-aminoxanilic acid 
• 106-50-3 1,4-phenylenediamine 
• 62-53-3 aniline 
• 52578-66-2 p-(acetylamino)phenyl azide 
• 659-49-4 4-nitrosoaniline 
• 80460-73-7 (4-aminophenyl)boronic acid hydrochloride 

Downstream Products

• 106-50-3 1,4-phenylenediamine 
• 17625-83-1 N-(4-aminophenyl)benzamide 
• 345204-05-9 (2S,5R,6R)-6-{[1-(4-Amino-phenyl)-1H-[1,2,3]triazol-4-yl]-hydroxy-methyl}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 52578-66-2 p-(acetylamino)phenyl azide 
• 538-41-0 4,4'-Diaminoazobenzene 
• 538-41-0 4-[(E)-(4-aminophenyl)diazenyl]phenylamine 
• 659-49-4 4-nitrosoaniline 
• 100-01-6 4-nitro-aniline 
• 4377-73-5 2,5-cyclohexadiene-1,4-diimine 

Relevant articles and documents

Synthesis of Nitro-Aryl Functionalised 4-Amino-1,8-Naphthalimides and Their Evaluation as Fluorescent Hypoxia Sensors

Fluorescent sensors are a vital research tool, enabling the study of intricate cellular processes in a sensitive manner. The design and synthesis of responsive and targeted probes is necessary to allow such processes to be interrogated in the cellular environment. This remains a challenge, and requires methods for functionalisation of fluorophores with multiple appendages for sensing and targeting groups. Methods to synthesise more structurally complex derivatives of fluorophores will expand their potential scope. Most known 4-amino-1,8-naphthalimides are only functionalised at imide and 4-positions, and structural modifications at additional positions will increase the breadth of their utility as responsive sensors. In this work, methods for the incorporation of a hypoxia sensing group to 4-amino-1,8-naphthalimide were evaluated. An intermediate was developed that allowed us to incorporate a sensing group, targeting group, and ICT donor to the naphthalimide core in a modular fashion. Synthetic strategies for attaching the hypoxia sensing group and how they affected the fluorescence of the naphthalimide were evaluated by photophysical characterisation and time-dependent density functional theory. An extracellular hypoxia probe was then rationally designed that could selectively image the hypoxic and necrotic region of tumour spheroids. Our results demonstrate the versatility of the naphthalimide scaffold and expand its utility. This approach to probe design will enable the flexible, efficient generation of selective, targeted fluorescent sensors for various biological purposes.

Discovery of Cell-Permeable O-GlcNAc Transferase Inhibitors via Tethering in Situ Click Chemistry

O-GlcNAc transferase (OGT) is a key enzyme involved in dynamic O-GlcNAcylation of nuclear and cytoplasmic proteins similar to phosphorylation. Discovery of cell-permeable OGT inhibitors is significant to clarify the function and regulatory mechanism of O-GlcNAcylation. This will establish the foundation for the development of therapeutic drugs for relevant diseases. Here, we report two cell-permeable OGT inhibitors (APNT and APBT), developed from low-activity precursors (IC50 > 1 mM) via “tethering in situ click chemistry (TISCC)”. Both of them were able to inhibit O-GlcNAcylation in cells without significant effects on cell viability. Unusual noncompetitive inhibition of OGT was helpful to discover novel inhibitors and explore the regulatory mechanism of OGT. The development of these molecules validates that TISCC can be utilized to discover novel lead compounds from components that exhibited very weak binding to the target.

Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate

An efficient approach to aryl azides, in short reaction times and good to excellent yields, has been developed via the reaction of aryl halides with sodium azide under Cu2O/tetraethylammonium prolinate catalysis.

Chloromethylated polystyrene supported copper (II) bis–thiazole complex: Preparation, characterization and its application as a heterogeneous catalyst for chemoselective and homoselective synthesis of aryl azides

This work deals the synthesis of aryl azides catalyzed by heterogeneous copper (II) complex of 3,5–bis (2–benzothiazolyl) pyridine, [Cu (II)(BTP)(OTf)2], immobilized on chloromethylated polystyrene, [Cu (II)(BTP)(OTf)2]@CMP. The prepared catalyst was characterized by different analytical techniques such as X-ray diffraction (XRD), thermogravimetric analysis (TGA), field emission scanning electron microscopy (SEM), energy dispersive X–ray spectroscopy (EDX), elemental analysis, and FT-IR and UV–Vis spectroscopic methods. This catalytic system showed excellent activity in the synthesis of aryl azides by the reaction of aryl halides with sodium azide in the presence of catalytic amounts of [Cu (II)(BTP)(OTf)2]@CMP. Moreover, this unique catalyst could be recovered easily and reused several times without any considerable loss of its catalytic activity.

Capping Strategies for Covalent Template-Directed Synthesis of Linear Oligomers Using CuAAC

Covalent templating provides an attractive solution to the controlled synthesis of linear oligomers because a template oligomer can be used to define the precise length and sequence of the product. If the monomer units are attached to the template using kinetically inert covalent bonds it should be possible to operate at high dilution to favor intramolecular over intermolecular reaction. However, for oligomerization reactions using copper-catalyzed azide alkyne cycloaddition (CuAAC) this is not the case. The rate-limiting step is formation of an activated copper complex, so any alkyne that is activated by copper reacts rapidly with the nearest available azide. As a result, every time a chain end alkyne is activated, rapid intermolecular reaction takes place with a different oligomer leading to the formation of higher order products. It proved possible to block these intermolecular reactions by adding an excess of an azide capping agent that intercepts the chain end of the growing oligomer on the template. By adjusting the concentration of the capping agent to compete effectively with the unwanted intermolecular reactions without interfering with the desired intramolecular reactions, it was possible to obtain quantitative yields of copy strands from covalent template-directed oligomerization reactions. Remarkably, the capping agent could also be used to control the stereochemistry of the duplex formed in the templated oligomerization reaction to give exclusively the antiparallel product.

Unsymmetric Bistable [c2]Daisy Chain Rotaxanes which Combine Two Types of Electroactive Stoppers

Mechanically interlocked molecules (MIMs) have emerged as intriguing building blocks for the construction of stimuli-responsive devices and materials. A particularly interesting and well-implemented subclass of MIMs is composed of symmetric bistable [c2]daisy chain rotaxanes. Topologically, they consist in the double thread of two symmetric macrocycles that are covalently linked to an axle bearing two switchable stations and a bulky stopper to avoid unthreading. Herein we report the synthesis and characterization of a series of unsymmetric bistable [c2]daisy chain rotaxanes that present two different electroactive units as stoppers (an electron donor triarylamine and an electron acceptor perylene bisimide unit). Using a combination of 1D and 2D NMR along with cyclic voltammetry, we demonstrate that the pH actuation of the mechanical bond can be used to modulate the electrochemical properties of the bistable [c2]daisy chain rotaxanes when switching between the contracted and extended forms.