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Chlorocyclohexane(cyclo chlorohexane) is a synthetic organic compound, CAS 542-18-7, with the molecular formula C6H11Cl, containing a chlorine atom and a cyclic six membered carbon molecular structure. Colorless transparent liquid, odorless, volatile, highly flammable, and highly irritating to eyes and skin. It has special physical and chemical properties and is widely used in the chemical industry. As an important intermediate in organic synthesis and catalytic reactions, it is widely used in organic chemistry, chemical industry, medicine, and agricultural production. For example, it can be used to synthesize organic compounds such as esters, fatty acids, aldehydes, ketones, hydrocarbons, etc.
The structure is composed of 6 carbon atoms, 11 hydrogen atoms, and 1 chlorine atom. Carbon atoms are interconnected by single bonds, forming a circular structure. The chlorine atom replaces one of the hydrogen atoms on the ring. This structural characteristic gives it a stable circular structure and specific substituents. There is a circular structure in the molecule, known as the benzene ring. A benzene ring is a six membered ring composed of six carbon atoms, each connected by a single bond. The shape and size of the ring maintain a fixed characteristic, which gives the benzene ring unique stability. This stability is due to the optimization of spatial arrangement and electron distribution brought about by the circular structure. Chlorine atoms are an important substituent of product. The chlorine atom replaces a hydrogen atom in the benzene ring, forming a chloride compound. The position of this chlorine atom on the benzene ring makes it an effective electrophilic substituent. This gives productspecific reactivity and activity in chemical reactions.

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Chemical Formula |
C6H11Cl |
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Exact Mass |
118 |
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Molecular Weight |
119 |
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m/z |
118 (100.0%), 120 (32.0%), 119 (6.5%), 121 (2.1%) |
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Elemental Analysis |
C, 60.76; H, 9.35; Cl, 29.89 |


Pharmaceutical Intermediates
In the pharmaceutical synthesis process, chlorocyclohexane can be utilized to produce drugs with specific therapeutic effects. For instance, it can be converted into compounds that exhibit anti-epileptic and anti-spasmodic properties, which are essential for the treatment of neurological disorders, such as trihexyphenidyl hydrochloride. These properties make it a key raw material in the development of certain medications.
Trihexyphenidyl hydrochloride is a commonly prescribed medication used to treat conditions like Parkinson's disease, dystonia, and other movement disorders. It works by blocking the action of acetylcholine, a neurotransmitter involved in muscle contraction, thereby reducing muscle spasms and improving motor control.

Pesticide Intermediates
It is also an intermediate in the production of certain pesticides, such as tricyclohexyltin.
Tricyclohexyltin, also known as tri(cyclohexyl)tin or TCHT, is an organotin compound with a wide range of applications, particularly in the agricultural sector. It is primarily used as a pesticide, exhibiting both insecticidal and acaricidal properties. This makes it effective against a variety of pests, including insects and mites, which can damage crops and reduce yield.
Rubber Antiscorching Agent
Prevention of Premature Vulcanization: During the processing of rubber, premature vulcanization can lead to undesirable properties in the final product, such as reduced flexibility, increased brittleness, and a lower overall quality. It acts as an effective antiscorching agent by inhibiting the vulcanization process at inappropriate times, thereby ensuring that vulcanization occurs only during the intended stage of production.

Improved Processing Stability: The use helps to stabilize the rubber compound during processing, allowing for more consistent and predictable manufacturing outcomes. This stability is crucial for achieving the desired physical and chemical properties of the final rubber product.
Enhanced Durability and Performance: By preventing premature vulcanization, it contributes to the overall durability and performance of the rubber product. The final product is likely to exhibit better resistance to wear and tear, as well as improved resistance to environmental factors such as heat and chemicals.
Polymer field
In latex polymerization, it serves as a stabilizer and prepolymer. It plays a crucial role in controlling the size and shape of polymer particles, ensuring that they are uniform and consistent. This uniformity is essential for achieving the desired physical and chemical properties of the final polymer product. Additionally, it enhances the stability of emulsions, preventing them from separating or breaking down during processing.

Beyond its use in latex polymerization, it can also react with other monomers to synthesize polymer materials with exceptional properties. Through carefully controlled reactions, it can be incorporated into polymer chains, altering their structure and imparting new and improved characteristics. These properties can include enhanced durability, flexibility, chemical resistance, and more.

At present, there are three main methods for the preparation of chlorocyclohexane: cyclohexane chloride, cyclohexene chloride catalyzed by sodium hydroxide and benzylcyclohexane chloride.
Cyclohexane chloride
It is the traditional method for preparing product.
C6H12 + Cl2 → C6H11Cl + HCl
The reaction conditions of this method are relatively mild, usually react at 100 ° C, and the reaction time is shorter. However, the reaction mixture will contain a large amount of chloride that is not easy to strip, and it is necessary to obtain pure product through complicated separation steps.
Sodium hydroxide catalyzes the chlorination of cyclohexene
Sodium hydroxide catalyzed chlorination of cyclohexene is a novel method for preparing product.
C6H10 + Cl2 → C6H11Cl
The method has mild reaction conditions, high product purity, and easy separation and purification of the reaction product. However, a catalyst needs to be added in the reaction of this method, and the catalyst may affect the purity and yield of the product.
Benzylcyclohexane chloride
Benzylcyclohexane chloride is a relatively new synthesis method of product.
C6H11-C6H5Cl + AlCl3 → C6H11Cl + C6H5AlCl2
This method has the advantages of high reaction yield, short reaction time, and high purity of the reaction product, but it needs to use toxic benzyl chloride, the reaction conditions are relatively harsh, and complicated separation treatment is required.

discovery history
The discovery history of it can be traced back to the early 19th century. During this period, organic chemists began to study natural compounds and discovered many new organic compounds. One such area of research is cyclic compounds.
The earliest research on cyclic compounds dates back to 1825, when French chemist Jean-Baptiste Dumas discovered a cyclic compound while studying the natural substance nutmeg. At the time, however, no one knew its structure or chemistry. Later, in 1865, while studying cholesterol and other organic compounds, French chemists Henri Etienne Sainte-Claire Deville and Paul Villiers discovered cyclohexane. Although the structure and chemistry of cyclohexane had yet to be determined, their work provided the basis for later research.
The research on it can be traced back to the end of the 19th century and the beginning of the 20th century. During this period, organic chemists began to explore ways to introduce chlorine atoms into cyclic compounds. One method is the catalytic chlorination of cyclohexyl with stannous chloride (SnCl2) or copper chloride (CuCl). The chemists then investigated the reaction of the chlorinated cyclohexyl group and found that it could react with other organics such as alcohols, derivative ethers and esters. These reactions provide product with a wide range of applications as chemical intermediates.
Although research on chlorocyclohexane began as early as the late 19th and early 20th centuries, its structure remains controversial. It was not until the middle of the 20th century that its exact structure was determined by spectroscopic techniques such as nuclear magnetic resonance (NMR) and mass spectrometry (MS).
Other properties
Chlorocyclohexane, a colorless to light yellow liquid with a distinctive odor, exhibits remarkable stability under typical environmental conditions. Its solubility characteristics are such that it is only slightly miscible with water but readily dissolves in organic solvents, including ether, alcohol, and benzene. This chemical compound exists in multiple isomeric forms, each distinguished by the specific position of the chlorine atom attached to the cyclohexane ring. These isomers display variations in their physical properties, such as melting point, boiling point, and density, as well as in their chemical reactivity. The distinct positions of the chlorine atom influence the ease with which other chemical reactions can occur, making some isomers more suitable for particular synthetic pathways than others. Understanding these isomer-specific differences is crucial for harnessing the potential in the synthesis of various chemicals for industrial applications.
Frequently Asked Questions
What is chlorocyclohexane?
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Chlorocyclohexane, with the CAS number 542-18-7, is an organic compound characterized by a cyclohexane ring with a chlorine atom substituent. It is a colorless to pale yellow liquid at room temperature, exhibiting a distinctive sweet odor.
What is the common name for cyclohexanone?
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Cyclohexanone (also known as oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone or ketocyclohexane) is a six-carbon cyclic molecule with a ketone functional group. It is a colorless, oily liquid with an acetone-like smell.
How to distinguish between chlorobenzene and chlorocyclohexane?
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Chlorobenzene is an aromatic organic compound having the chemical formula C6H5Cl, while chlorocyclohexane is an organic compound having the chemical formula C6H11Cl. The key difference between chlorobenzene and chlorocyclohexane is that in their chemical structure.
What are the hazards of cyclohexyl chloride?
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Cyclohexyl Trichlorosilane is a CORROSIVE CHEMICAL and contact can cause severe skin and eye irritation and burns leading to permanent eye damage.
What are the uses of cyclohexanone?
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Cyclohexanone is used as a solvent in insecticides, wood stains, paint and varnish removers, spot removers, cellulosics, and natural and synthetic resins and lacquers.
Is cyclohexanone safe?
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Cyclohexanone may damage the liver and kidneys. OSHA: The legal airborne permissible exposure limit (PEL) is 50 ppm averaged over an 8-hour workshift. NIOSH: The recommended airborne exposure limit (REL) is 25 ppm averaged over a 10-hour workshift.
What is cyclohexanone used for in pesticides?
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Cyclohexanone is a major precursor for nylon production and is also used as a pesticide solvent. In this study, cyclohexanone was evaluated as a fumigant against rice weevil adults, confused flour beetle adults, western flower thrips larvae and adults, spotted wing drosophila adults, and subterranean termite workers.
What is methylcyclohexane also known as?
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Methylcyclohexane is defined as an aliphatic hydrocarbon with the molecular formula C7H14, characterized by a colorless liquid state and a boiling point of 100.0 °C. It is commonly known as cyclohexylmethane and has various health and safety classifications indicating its flammability and potential health hazards.
Why is chlorocyclohexane more polar than chlorobenzene?
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As a result the s p 2 hybrid of C - Cl bond in chlorobenzene has less tendency to release electron to Cl than the s p 3 hybrid carbon of cyclohexyl chloride. As a result, the C - Cl bond in chlorobenzene is less polar than in cyclohexyl chloride. Thus chlorobenzene is less polar than cyclohexyl chloride.
Are benzene and chlorobenzene the same?
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Chlorobenzene is defined as an industrially synthesized compound derived from benzene through chlorination, commonly used as a solvent and in the production of herbicides and other chemical products.
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