1942-61-6

Usage

Uses

Used in Organic Synthesis:
Azobenzene-4-yl isocyanate is employed as a reactive intermediate in organic synthesis for the creation of various chemical compounds. Its reactivity allows it to participate in a range of chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Research:
In the field of chemical research, Azobenzene-4-yl isocyanate is used as a research tool to study the properties and reactions of isocyanate compounds. Its unique structure and reactivity provide insights into the behavior of related compounds and contribute to the advancement of chemical knowledge.
Used in Pharmaceutical Development:
Azobenzene-4-yl isocyanate may also be utilized in the development of pharmaceuticals, where its reactive nature can be harnessed to create new drug candidates or to modify existing ones, potentially leading to improved therapeutic agents.
Used in Material Science:
In material science, Azobenzene-4-yl isocyanate could be explored for its potential applications in the creation of new materials with specific properties, such as polymers with tailored characteristics for various industrial applications.

InChI:InChI=1/C13H9N3O/c17-10-14-11-6-8-13(9-7-11)16-15-12-4-2-1-3-5-12/h1-9H/b16-15+

Upstream product

• 75-44-5 phosgene 
• 60-09-3 aniline yellow 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 13201-81-5 N,N'-bis-(4-phenylazo-phenyl)-urea 
• 92166-43-3 (4-phenylazo-phenyl)-carbamic acid methyl ester 
• 93311-68-3 (4-phenylazo-phenyl)-carbamic acid propyl ester 
• 95291-05-7 (4-phenylazo-phenyl)-carbamic acid octyl ester 
• 95747-68-5 (4-phenylazo-phenyl)-carbamic acid undecyl ester 
• 124715-88-4 (4-phenylazo-phenyl)-carbamic acid pentadecyl ester 
• 6275-71-4 <4-Benzolazo-phenyl>-carbamidsaeure-aethylester 
• 95427-73-9 (4-phenylazo-phenyl)-carbamic acid hex-3c-enyl ester 
• 56777-63-0 N-(4-phenylazo-phenylcarbamoyl)-l-alanine 

Relevant academic research and scientific papers

Visible colorimetric fluoride ion sensors

(Chemical Equation Presented) Five new urea derivative naphthalene compounds were synthesized by a reaction of 1,8-diaminonaphthalene and the corresponding isocyanates and showed a distinct color change only when treated with fluoride ions.

Introducing a photo-switchable azo-functionality inside Cr-MIL-101-NH 2 by covalent post-synthetic modification

For the first time an azo functionality was covalently introduced into a MOF by post-synthetic modification. The reaction of Cr-MIL-101-NH2 with p-phenylazobenzoylchloride (1) and 4-(phenylazo)phenylisocyanate (2) as the reactants led to the compounds Cr-MIL-101-amide and Cr-MIL-101-urea, with the azo groups protruding into the mesoporous cages. XRPD and N2 sorption measurements confirm the intactness of the framework and the successful covalent modification was proven by IR- and NMR-spectroscopy. Furthermore, cis/trans isomerisation upon irradiation with light was demonstrated by UV/Vis spectroscopy. More distinct changes in the UV/Vis spectra were observed for Cr-MIL-101-amide compared to Cr-MIL-101-urea, while the degree of functionalization, i.e. the number of reacted NH2-groups, seems to have a less pronounced effect. The variation of the sorption properties due to the cis/trans isomerisation was proven by methane adsorption measurements.

Development of a photoswitchable antagonist of NMDA receptors

N-methyl–Daspartate receptors (NMDARs) are vital for neurological processes such as learning, memory, and synaptic plasticity. As such, small molecules that modulate their function are of interest in the study of numerous neurological diseases. We have synthesized a small library of photoswitches that modulate NMDAR function. The most efficient photoswitch to date is based on a known ligand of the glycine binding site and shows significant subtype selectivity.

Postpolymerization modification of hydroxyl-functionalized polymers with isocyanates

The postpolymerization functionalization of hydroxyl-group terminated polymers (Mn in the range of 1000-6000 g mol-1) such as poly(ethylene glycol) (PEG), poly(N-isopropylacrylamide) (PNIPAM), poly(N,N-dimethylacrylamide) (PDMAM), and poly(tert-butyl acrylate) (PtBA) with a wide range of functional isocyanate derivatives such as azobenzene, viologen, and anthracene has been investigated. It was shown by 1H and 13C NMR, GPC, Fourier transform infrared spectroscopy (FTIR), and electrospray ionization mass spectrometry (ESI-MS) that a high degree of end-group conversion, typically >98%, with little or no formation of side products can be achieved at ambient temperature. PNIPAM, PDMAM, PtBA, and PHEAM polymers have been obtained by reversible addition-fragmentation chain transfer (RAFT) radical polymerization from a hydroxyl-group containing chain transfer agent (CTA). The formation of the carbamate has been shown to be compatible with the trithiocarbonate end-group of the RAFT polymers. Additionally, this approach allows for the direct functionalization of RAFT polymers without the need of additional steps such as deprotection or aminolysis of the CTA. This route was subsequently used for the preparation of a variety of side-chain functional polymers from poly(N-hydroxyethyl acrylamide) (PHEAM). Three different high yielding methods have been employed to prepare the isocyanates (R-NCO). Either amino or carboxylic acid precursors have been converted into the desired R-NCO or hydroxyl group moieties have been reacted with an excess of 1,6-hexamethylene diisocyanate (HDI) to statistically form the monofunctional product.