19573-22-9

Usage

Uses

Used in Chemical Synthesis:
Azidocyclohexane is used as a reactant in the preparation of sulfonyl tetrazoles. This application takes advantage of the Huisgen dipolar cycloaddition reaction between azides and toluenesulfonyl cyanide (T631000), which is a key step in the synthesis of various chemical compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, azidocyclohexane can be utilized as a building block for the development of novel drugs, particularly those targeting specific biological pathways or receptors. Its unique reactivity allows for the creation of diverse molecular structures with potential therapeutic properties.
Used in Material Science:
Azidocyclohexane can also be employed in the development of new materials with specific properties, such as improved mechanical strength, chemical resistance, or thermal stability. Its incorporation into polymers or other materials can lead to the creation of advanced materials for various applications, including automotive, aerospace, and electronics industries.

Synthesis Reference(s)

Tetrahedron Letters, 18, p. 1977, 1977 DOI: 10.1016/S0040-4039(01)83657-1

InChI:InChI=1/C6H12N3/c7-9-8-6-4-2-1-3-5-6/h6-7H,1-5H2/q+1

Upstream product

• 108-85-0 1-bromocyclohexane 
• 626-62-0 Cyclohexyl iodide 
• 953-91-3 cyclohexyl tosylate 
• 110-83-8 cyclohexene 
• 110-82-7 cyclohexane 
• 546-67-8 lead(IV) tetraacetate 
• 110-86-1 pyridine 
• 16156-56-2 cyclohexyl mesylate 
• 1569-69-3 Cyclohexanethiol 
• 108-93-0 cyclohexanol 
• 709-83-1 2-(cyclohexyloxy)tetrahydro-2H-pyran 
• 108-91-8 cyclohexylamine 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2044-08-8 1-bromocyclohex-1-ene 

Downstream Products

• 59574-46-8 2-butyl-5-(4-chloro-phenylimino)-4-cyclohexyl-[1,2,4]thiadiazolidin-3-one 
• 10108-56-2 N-butylcyclohexylamine 
• 5459-93-8 N-ethyl-cyclohexanamine 
• 108630-79-1 1-cyclohexyl-5-acetyltetrazole 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 1821-36-9 N-phenyl-2-cyclohexylamine 
• 65245-33-2 C₁₃H₁₉N₅ 
• 64724-55-6 8-cyclohexyl-1,2,4,5-tetrakis-trifluoromethyl-(1rH,2tH,4tH,5cH)-3-thia-6,7,8-triaza-tricyclo[3.3.0.0^2,4]oct-6-ene 
• 4998-76-9 cyclohexylamine hydrochloride 
• 108-91-8 cyclohexylamine 
• 791-28-6 Triphenylphosphine oxide 
• 1126-56-3 N-cyclohexylpropanamide 
• 66949-28-8 (cyclohexylimino)triphenylphosphorane 
• 40649-25-0 cyclohexyl-cyclopentyl-amine 

Relevant academic research and scientific papers

Silver-Catalyzed Decarboxylative Azidation of Aliphatic Carboxylic Acids

The catalytic decarboxylative nitrogenation of aliphatic carboxylic acids for the synthesis of alkyl azides is reported. A series of tertiary, secondary, and primary organoazides were prepared from easily available aliphatic carboxylic acids by using K2S2O8 as the oxidant and PhSO2N3 as the nitrogen source. The EPR experiment sufficiently proved that an alkyl radical process was generated in the process, and DFT calculations further supported the SET process followed by a stepwise SH2 reaction to afford azide product.

A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone(DDQ)/n-Bu4NN3 system

Alcohols, thiols, and silyl ethers are converted into alkyl azides in good to excellent yields by treatment with PPh3/DDQ/n-Bu 4NN3 in CH2Cl2 at room temperature. The method is highly selective for 1°

THE IR AND RAMAN SPECTRA AND CONFORMATIONS OF CYCLOHEXYL AZIDE

Cyclohexyl azide was synthesized and the vibrational spectra recorded in several phases including: liquid at various temperatures, amorphous and crystalline at 90 K and high pressure crystal at ca. 60 kbar.Additional IR spectra were recorded in argon and

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

Conformational energy (A-value) of the 4-phenyl-1,2,3-triazolyl group

Conformational energy (A-value) of the 4-phenyl-1,2,3- triazolyl group was estimated as 2.0 kcal mol–1 (8.5 kJ mol–1) using 1H NMR-based conformational study for a set of (4-phenyl-1,2,3-triazol-1-yl)cyclohexanes. This provides a reasonable estimation als

Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions

Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.

Visible-Light-Mediated Strategies to Assemble Alkyl 2-Carboxylate-2,3,3-Trisubstituted β-Lactams and 5-Alkoxy-2,2,4-Trisubstituted Furan-3(2H)-ones Using Aryldiazoacetates and Aryldiazoketones

Two new visible-light-mediated strategies are described starting from aryldiazoacetates. The first approach describes their reaction with azides to afford the corresponding imines, and then reaction with aryldiazoketones produces alkyl 2-carboxylate-2,3,3

Furfuryl Cation Induced Three-Component Reaction to Synthesize Triazole-Substituted Thioesters

A furfuryl cation induced three-component thioesterification reaction between thiols, 5-bromo-2-furylcarbinols and azides is reported. This metal-free method relies on the acetyl chloride/HFIP-mediated cascade formal [3+2] cycloaddition/ring-opening/thioesterification, which allows the efficient construction of a series of complex triazole-thioesters linked with an (Z)-olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.

Synthesis, characterization and catalytic properties of a new binuclear copper(II) complex in the azide–alkyne cycloaddition

A new binuclear copper(II)–oxalate complex containing 2,9-dimethyl-1,10-phenanthroline (dmp), was synthesized via a simple and one-pot reaction. [Cu2(dmp)2(ox)Cl2]·H2O (1) was characterized by single-crystal X-ray crystallography and IR methods. The complex 1 was been used to efficiently catalyze the three-component 1,3-Dipolar cycloaddition CuAAC reaction to produce 1,4-disubstituted 1,2,3‐triazoles in good to excellent yields from aromatic or aliphatic halide, sodium azide, and acetylene in water as a green solvent with low catalyst amount.