4435-18-1

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexylideneacetonitrile is used as an intermediate in the production of pharmaceuticals for its ability to facilitate the synthesis of complex organic molecules that are integral to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, cyclohexylideneacetonitrile is employed as an intermediate in the synthesis of various agrochemicals, contributing to the development of effective crop protection agents and other agricultural products.
Used in Organic Synthesis:
Cyclohexylideneacetonitrile is utilized as a solvent and reagent in organic synthesis, enabling the formation of a wide range of organic compounds due to its reactive nature and compatibility with various chemical reactions.
Safety and Storage:
Cyclohexylideneacetonitrile is stable under normal conditions but can react vigorously with strong oxidizing agents. It should be stored in a cool, dry place, away from heat, sparks, and open flames to prevent potential hazards. Proper safety measures and precautions are essential when handling cyclohexylideneacetonitrile to avoid exposure or contact with skin, eyes, and clothing.

InChI:InChI=1/C8H11N/c9-7-6-8-4-2-1-3-5-8/h6H,1-5H2

Upstream product

• 64-17-5 ethanol 
• 6975-71-9 1-cyclohexenylacetonitrile 
• 141-52-6 sodium ethanolate 
• 934-86-1 C-Cyclohexyliden-acetamid 
• 108-94-1 cyclohexanone 
• 372-09-8 cyanoacetic acid 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 59463-54-6 S-cyanomethyl O-ethyl carbonodithioate 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 75-05-8 acetonitrile 
• 177-10-6 1,3-dioxolane-2-spirocyclohexane 
• 36993-53-0 Trimethylsilylchloroacetonitrile 
• 107-14-2 chloroacetonitrile 
• 63830-87-5 2-trimethylsilyl-1-oxaspiro<2.5>octane 

Downstream Products

• 6975-71-9 1-cyclohexenylacetonitrile 
• 4435-14-7 2-cyclohexylacetonitrile 
• 54353-80-9 2-(cyclohex-1-en-1-yl)-2-methylpropanenitrile 
• 116998-11-9 2-(p-anisyl)-1-cyclohexenylacetonitrile 
• 116998-12-0 2-(p-anisyl)cyclohexylidenecetonitrile 
• 100-66-3 methoxybenzene 
• 116998-13-1 [2,2-Bis-(4-methoxy-phenyl)-cyclohex-(E)-ylidene]-acetonitrile 
• 91-20-3 naphthalene 
• 116998-14-2 2-(1-naphthyl)-1-cyclohexenylacetonitrile 
• 116998-15-3 2-(1-naphthyl)cyclohexylideneacetonitrile 
• 86613-67-4 Z-2-bromocyclohexylideneacetonitrile 
• 86613-64-1 E-2-bromocyclohexylideneacetonitrile 
• 4442-90-4 2-cyclohexylideneethan-1-amine 
• 204651-45-6 2-(1-amino-1-cyclohexyl)acetonitrile 

Relevant academic research and scientific papers

Synthesis of cyclohexylideneacetonitrile on zeolites

Condensation of cyclohexanone with acetonitrile on zeolites with different carcass structures was studied. The highest yield of cyclohexylideneacetonitrile (80 wt %) at a 98% selectivity of the process was attained with NaX zeolite containing 0.5 wt % KOH. Factors responsible for different catalytic activities and selectivities of zeolites are discussed.

Overcoming Selectivity Issues in Reversible Catalysis: A Transfer Hydrocyanation Exhibiting High Kinetic Control

Reversible catalytic reactions operate under thermodynamic control, and thus, establishing a selective catalytic system poses a considerable challenge. Herein, we report a reversible transfer hydrocyanation protocol that exhibits high selectivity for the thermodynamically less favorable branched isomer. Selectivity is achieved by exploiting the lower barrier for C-CN oxidative addition and reductive elimination at benzylic positions in the absence of a cocatalytic Lewis acid. Through the design of a novel type of HCN donor, a practical, branched-selective, HCN-free transfer hydrocyanation was realized. The synthetically useful resolution of a mixture of branched and linear nitrile isomers was also demonstrated to underline the value of reversible and selective transfer reactions. In a broader context, this work demonstrates that high kinetic selectivity can be achieved in reversible transfer reactions, thus opening new horizons for their synthetic applications.

Amination of Carbenium Ions Generated by Directed Protonolysis of Cyclopropane

Directed intramolecular protonolyis of the cyclopropane C-C bond is demonstrated as a strategy to generate carbenium ions. This intermediate can be subjected to amination with nitriles under Ritter reaction conditions. Directing groups such as carbamate, carboxamide, urea, ester, and ketone were found to be efficient for regioselective anti-Markovnikov cleavage of cyclopropane. Depending on the directing group, the amination provided orthogonally protected 1,4-diamine, ?-amino carboxylic, and ?-amino ketone derivatives.

Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization

A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.

Organocatalytic, Asymmetric Eliminative [4+2] Cycloaddition of Allylidene Malononitriles with Enals: Rapid Entry to Cyclohexadiene-Embedding Linear and Angular Polycycles

A direct aminocatalytic synthesis has been developed for the chemo-, regio-, diastereo-, and enantioselective construction of densely substituted polycyclic carbaldehydes containing fused cyclohexadiene rings. The chemistry utilizes, for the first time, remotely enolizable π-extended allylidenemalononitriles as electron-rich 1,3-diene precursors in a direct eliminative [4+2] cycloaddition with both aromatic and aliphatic α,β-unsaturated aldehydes. The generality of the process is demonstrated by approaching 6,6-, 5,6-, 7,6-, 6,6,6-, and 6,5,6-fused ring systems, as well as biorelevant steroid-like 6,6,6,6,5- and 6,6,6,5,6-rings. A stepwise reaction mechanism for the key [4+2] addition is proposed as a domino bis-vinylogous Michael/Michael/retro-Michael reaction cascade. The utility of the malononitrile moiety as traceless activating group of the dicyano nucleophilic substrates is demonstrated.

Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation

A novel direct transformation of aliphatic terminal alkynes to alkenyl nitriles through the incorporation of a nitrogen atom into the simple hydrocarbons has been reported. The usage of inexpensive copper catalyst, O2 as the sole oxidant, broad substrate scope as well as feasibility for "late-stage modification" make this protocol very promising. Mechanistic studies including DFT calculation demonstrate a novel 1,2-hydride shift process for this novel nitrogenation reaction.

GEMINALLY SUBSTITUTED CYANOETHYLPYRAZOLO PYRIDONES AS JANUS KINASE INHIBITORS

The instant invention provides compounds of Formula (I) which are JAK inhibitors, and as such are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.

Mg-Al layered double hydroxides: Synthesis, structure, and catalytic potential in condensation of cyclohexanone with acetonitrile

Basic properties of synthetic Mg-Al layered double hydroxides were studied. It was shown that these properties strongly depend on the chemical composition and calcination temperature and are of key importance for determining the activity of catalysts based on these compounds. A relationship was found between the basic properties of these materials and the selectivity of conversion of the starting reagents to N-cyclohexylideneacetonitrile in condensation of cyclohexanone with acetonitrile.

Synthesis and applications of quaternized highly branched polyacrylamide as a novel multi-site polymeric phase transfer catalyst

In current study, quaternized highly branched polyacrylamide (HBAA) was synthesized and used as an efficient multi-site polymeric phase transfer catalyst in nucleophilic substitution reactions and also in synthesis of α, β-unsaturated nitriles from reaction of acetonitrile and carbonyl compounds. The quaternized HBAA was synthesized via two steps. First, HBAA was synthesized via self-condensing vinyl polymerization of acrylamide at appropriate molar ratio of monomer to diperiodatocuprate(III). In the second step, 3-acrylamidopropyl trimethylammonium iodide was polymerized on peripheral area of the HBAA in the presence of diperiodatocuprate(III) solution again. The thermal behavior of HBAA and that of the quaternized HBAA were studied by DSC and TGA analysis. This phase transfer catalyst was easily recovered after reaction and reused several times without any loss of activity.

Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones

α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR 3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2/su