1121-21-7

Usage

Uses

Used in Agrochemical Production:
1,2-Dichlorocyclohexane is used as a synthetic intermediate for the production of agrochemicals, contributing to the development of compounds that protect crops from pests and diseases, thereby ensuring agricultural productivity.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1,2-Dichlorocyclohexane serves as a key intermediate, facilitating the synthesis of various medicinal compounds that address a range of health conditions.
Used as a Solvent:
1,2-Dichlorocyclohexane is utilized as a solvent in certain chemical processes, leveraging its properties to dissolve other substances and enable reactions to occur.
Used in Organic Compound Synthesis:
Beyond its direct applications, 1,2-Dichlorocyclohexane is also employed as a synthetic intermediate in the production of other organic compounds, expanding its utility across multiple chemical synthesis pathways.
Environmental Considerations:
Given its toxicity to aquatic organisms and potential for causing long-term environmental harm, 1,2-Dichlorocyclohexane necessitates careful handling and disposal to mitigate risks to both human health and ecological systems.

Upstream product

• 128-09-6 N-chloro-succinimide 
• 110-83-8 cyclohexene 
• 56-23-5 tetrachloromethane 
• 110-01-0 thiophene 
• 27334-16-3 trans-2-chlorocyclohexyltellurium trichloride 
• 6628-80-4 trans-2-chlorocyclohexanol 
• 64-19-7 acetic acid 
• 7182-86-7 tetrabutylammonium p-toluenesulfonate 
• 65411-49-6 tetrabutylammonium methanesulfonate 
• 108-93-0 cyclohexanol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 3135-74-8 chlorourea 
• 7732-18-5 water 

Downstream Products

• 16069-36-6 perhydrodibenzo-18-crown-6 
• 84-14-0 1,2-diphenyl-cyclohexane 
• 87-82-1 hexabromobenzene 
• 318292-43-2 1,2-cyclohexane dicarboxylic acid di-isononylester 
• 110-83-8 cyclohexene 

Relevant academic research and scientific papers

Electrochemical Acylation of Some Cyclic Olefins by Using Aluminium Anode

The electrochemical acylation of cyclohexene, cycloheptene and their 1-methyl derivatives produces alkyl-cycloalkenyl ketones in good yields.The unsubstituted cycloalkenes give α,β-unsaturated ketones, whereas the 1-substituted derivatives yield mixtures of α,β- and β,γ-unsaturated ketones in which the latter products are predominant.

Iron(II)-induced activation of 1:1 HOOH/HCl for the chlorohydroxylation of olefins and the chlorination of hydrocarbons: Chlorinated fenton chemistry

Iron complexes [FeII(OPPh3)42+, FeII(bpy)2,2+, FeII(OH2)62+, and FeIIICl3] catalytically activate 1:1 HOOH/ HCl combinations for the efficient chlorohydroxylation of olefins. The reactive intermediate 7 is not HOCl, but appears to be formed via a Fenton process FeIILx2+ ? (B) [Lx+FeIIOOH(BH+)] (1) → (HCl) [LxFeIV(OH)Cl] (7) + H2O}. Although the major product from the reaction of 7 with olefin substrates (e.g., cyclohexene, C-C6H10) is the chlorohydroxo derivative [C-C6H10 + HOOH + HCl → (FeIILx) c-C6H10(OH)Cl + H2O], significant amounts of the dihydroxo [c-C6H10(OH)2] and traces of the dichloro [c-C6H10Cl2] derivatives are produced. The reaction efficiency with respect to HOOH/HC1 ranges from 51% for norbornene to 31% for cyclohexene to 10% for 1-hexene. The presence of dioxygen (O2) with c-C6H10 results in the production of some ketone [c-C6H8(O)] via oxygenated Fenton chemistry, but does not inhibit the chlorohydroxylation process. The catalyzed process is equally efficient and selective in a biphasic H2O/substrate solution as in acetonitrile. With cis-stilbene (cis-PhCH=CHPh) the major product is the epoxide (>80%); the reaction efficiency is 63% relative to HOOH/HCl. These systems chlorinate saturated hydrocarbons (c-C6H12 → c-C6H11Cl) and hydroxylate benzene (PhH → PhOH). Because 7 chlorohydroxylates olefins and chlorinates hydrocarbons in aqueous media much more efficiently than HOCl, its in-vivo analogue may be a reasonably reactive intermediate for "oxy-radical" damage in biological systems.

α-ELIMINATION OF ORGANIC HALIDES FROM ORGANOTELLURIUM(IV) HALIDES

Three types of α-elimination (oxidative, photolytic, and thermal) of organotellurium(IV) halides to give organic halides have been disclosed.Treatment of organotellurium(IV) halides with some oxidants, preferably t-butyl hydroperoxide in 1,4-dioxane, acet

Use of a Sacrificial Aluminum Anode in the Acylation of Some Olefins

The acylation of some alicyclic and aliphatic alkenes by the electrochemical generation of a catalyst using a sacrificial aluminum anode was investigated. Substrates were electrolyzed in a dichloromethane solution of an appropriate electrolyte (tetraalkylammonium salts) in the presence of an acylating agent (acetyl chloride or anhydride). Thus, unsubstituted cycloalkenes, namely cyclohexene and cycloheptene, gave by that reaction conjugated ketones, i.e. the corresponding 1-acetylcycloalkenes, as the only unsaturated carbonyl compounds in moderate-to-good yields. Under the same reaction conditions their 1-methyl derivatives gave mixtures of the corresponding conjugated and β,γ-unsaturated isomeric ketones in which unconjugated compounds predominate. In both cases unsaturated ketones were accompanied by different amounts of side products. Terminal aliphatic alkenes (1-hexene, 1-heptene, and 1-dodecene) afforded only conjugated a ketone with a normal skeleton, but in lower yields. The acylation of cyclohexene was studied in more detail, altering the reaction conditions by changing the reaction temperature, the supporting electrolyte, the acylating agent and the electrochemical cell. Mechanistic considerations were made on the basis of the products distribution and some theoretical calculations being made by the MOPAC program package (version 7.0).

Photoreduction of Thioether Gold(III) Complexes: Mechanistic Insight and Homogeneous Catalysis

Complexes formed between AuCl3 and thioether ligands underwent a photoinduced reductive elimination under homogeneous conditions in dichloromethane and toluene solutions to afford the corresponding AuI complexes. All the gold(III) complexes were rapidly reduced to the gold(I) chloride complexes under 365 nm irradiation or ambient light while being thermally stable below 55 °C. The mechanism of photoreduction through Cl2 elimination is discussed based on a kinetic study and the chemical trapping of chlorine species: Cl2, radical Cl., and possibly Cl+. The catalytic activities of the gold(III) chloride complexes and the corresponding gold(I) complexes obtained by in situ reduction were evaluated in the cyclization of N-propargylic amides to oxazoles. The merits of such photoreducible complexes in homogeneous gold catalysis are illustrated by a cascade reaction catalyzed by thioether gold complexes that affords a 4H-quinolizin-4-one in high yields.

Highly selective halogenation of unactivated C(sp3)-H with NaX under co-catalysis of visible light and Ag@AgX

The direct selective halogenation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and yields higher than 90%, with the chlorination of toluene being 81%, far higher than the 40% conversion using dichlorine. Mechanistic studies demonstrated that the reaction is a free radical process using blue light (450-500 nm), with visible light being the most effective light source. Irradiation is proposed to cause AgCl bonding electrons to become excited and electron transfer from chloride ions induces chlorine radical formation which drives the substitution reaction. The reaction provides a potentially valuable method for the direct chlorination of saturated hydrocarbons.

Chlorohydrination of allyl chloride with HCl and H2O2 catalyzed by hollow titanium silicate zeolite to produce dichloropropanol

Overall, over 95% of epichlorohydrin is industrially manufactured via the chlorohydrination route with hazardous Cl2 as a reagent, which brings serious operation and pollution problems. Herein, we describe a novel Cl2-free process for the synthesis of dichloropropanols from allyl chloride with H2O2 and HCl catalyzed by hollow titanium silicate zeolite under mild conditions. A high conversion and overall dichloropropanol selectivity exceeding 95% are simultaneously achieved, and the heterogeneous catalyst is highly stable and amenable for reuse. Comprehensive experimental and spectroscopic data suggest that the Lewis acidity of the framework Ti species has a synergistic effect with the Br?nsted acidity of HCl that promotes the epoxidation of allyl chloride and the ring opening of the epoxy groups.

Photochemical oxygenation of cyclohexene with water sensitized by aluminium(III) porphyrins with visible light

Aluminium(III)-tetramesitylporphyrin, with the Earth's the most abundant metal and the third most abundant element as the Al(III) ion, induces the photochemical oxygenation of cyclohexene in deaerated aqueous acetonitrile to form the corresponding epoxide and alcohol with water as both electron and oxygen atom donor upon visible light irradiation. The Al(III) should be the most available and meaningful element to be utilized in the artificial photosynthetic unit. The excited triplet state of the water-coordinated porphyrin is responsible for the photochemical oxygenation.

Visible light induced oxygenation of alkenes with water sensitized by silicon-porphyrins with the second most earth-abundant element

Silicon as the second most abundant element on Earth was effectively utilized as the central atom in the porphyrin to induce photochemical oxygenation of alkenes as the first example of photocatalytic reaction through activation of water molecule in the presence of K2PtCl6 as an electron acceptor. Oxygen atom of water was confirmed to be incorporated in the oxygenated product by the photoreaction with H218O. The excited triplet state of silicon porphyrin was revealed to be responsible for the photochemical oxygenation. The one-electron oxidized silicon porphyrin was predicted by DFT calculation to have its spin population mostly on the axially ligated hydroxyl oxygen atom. The oxyl radical character of the axial ligand could rationalize the oxygenation reaction.

1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources

1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.