1-Chloro-4-Ethynylbenzene
Linshang Chemical
HS Code |
908400 |
Chemical Formula | C8H5Cl |
Molecular Weight | 136.58 |
Appearance | colorless to light yellow liquid |
Boiling Point | 198 - 200 °C |
Melting Point | N/A |
Density | 1.14 g/cm³ |
Solubility In Water | Insoluble |
Solubility In Organic Solvents | Soluble in common organic solvents like ethanol, ether |
Flash Point | 73 °C |
Vapor Pressure | N/A |
Odor | Characteristic aromatic odor |
Stability | Stable under normal conditions |
As an accredited 1-Chloro-4-Ethynylbenzene factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
Packing | 1 - chloro - 4 - ethynylbenzene packaged in 100 - gram bottles for secure storage. |
Storage | 1 - Chloro - 4 - ethynylbenzene should be stored in a cool, dry, well - ventilated area, away from heat sources and ignition sources. It should be kept in a tightly - sealed container to prevent leakage and exposure to air and moisture. Store it separately from oxidizing agents and reactive chemicals to avoid potential reactions. |
Shipping | 1 - chloro - 4 - ethynylbenzene, a chemical, must be shipped in accordance with strict hazardous materials regulations. It should be in properly sealed, corrosion - resistant containers, labeled clearly, and transported by approved carriers following safety protocols. |
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In terms of its chemical activity, chlorine atoms and ethynyl groups endow it with activity. As a good leaving group, chlorine atoms are easily replaced by nucleophilic reagents in nucleophilic substitution reactions. Nucleophilic reagents, with their electron-rich properties, attack the carbon atoms connected to the chlorine atoms, and the chlorine atoms carry a pair of electrons away to form new organic compounds. This reaction is widely used in the construction of carbon-heteroatomic bonds.
And ethynyl groups contain carbon-carbon three bonds, and their chemical properties are abnormal. First, the triple bond can undergo an addition reaction. For example, when adding with hydrogen, under the action of an appropriate catalyst, it can be gradually hydrogenated to form a carbon-carbon double bond first, and then completely hydrogenated to become a carbon-carbon single bond. When adding with halogens, different addition products can be formed according to the reaction conditions and halogen dosage, such as dihalogenated olefins or tetrahalogenated alkanes.
In addition, ethynyl groups can also participate in a variety of special reactions. For example, under the catalysis of transition metals, coupling reactions can be carried out. With other halogenated hydrocarbons or compounds with suitable leaving groups, the construction of carbon-carbon bonds can be achieved through the action of metal catalysts, which is of great significance in the synthesis of complex organic molecules.
Furthermore, although the part of the benzene ring of 1-chloro-4-ethynylbenzene has certain stability, it can also undergo electrophilic substitution reaction. Because there are chlorine atoms and ethynyl groups attached to the benzene ring, the two have an impact on the electron cloud density distribution of the benzene ring, which changes the activity and selectivity of the electrophilic substitution reaction. Hydrogen atoms at different positions on the benzene ring have different reactivity when the electrophilic reagents attack due to the electronic effect of the substituents, which provides the possibility for the synthesis of specific substituted products.
1-chloro-4-ethynylbenzene, with its unique chemical properties of chlorine atom and ethylene group, plays a crucial role in the creation of various organic compounds in the field of organic synthesis chemistry, and is a key raw material and intermediate for many organic synthesis reactions.
In the process of organic synthesis, one of them is often used as a key intermediate to build complex organic structures. Because of its high reactivity of chlorine atoms and ethynyl groups, it can participate in multiple reactions. Such as nucleophilic substitution reactions, chlorine atoms can be replaced by many nucleophiles, thereby introducing other functional groups to lay the foundation for the construction of more complex molecules.
Furthermore, it is also useful in the construction of conjugated systems. The ethynyl group is conjugated to the benzene ring, and the conjugated structure can be expanded through appropriate reactions. This is crucial in the synthesis of materials with specific optoelectronic properties, such as in the field of organic semiconductor materials. Such conjugated structural molecules may exhibit unique electrical and optical properties, providing the possibility for the fabrication of new optoelectronic devices.
In addition, there may also be potential applications in the field of medicinal chemistry. Through subsequent modifications and reactions, it can be integrated into the molecular structure of drugs, which may endow drugs with different pharmacological activities, which is helpful for the development of new drugs. In conclusion, 1-chloro-4-ethynylbenzene plays an indispensable role in organic synthesis and related fields due to its unique structure and reactivity, opening a broad path for the creation of many compounds and the development of new materials.
First, it can be started from p-chlorobenzaldehyde. Shilling p-chlorobenzaldehyde and Phosphorus Ylide reagent perform a Wittig reaction, which can convert the aldehyde group into a double bond to obtain p-chlorophenylvinyl compounds. Subsequently, a suitable halogenating agent, such as bromine, is halogenated to the double bond under suitable conditions, and a halogen atom is introduced. Then a strong base, such as potassium tert-butyl alcohol, is used to treat the halogen. After the elimination reaction, the ethynyl group is formed, and 1-chloro-4-ethynylbenzene is obtained.
Second, we can also start from p-chlorobrombenzene. First, it interacts with magnesium chips in anhydrous ether and other solvents to make Grignard's reagent. After that, Grignard's reagent reacts with acetylene halide, such as acetylene bromide, in the presence of a suitable catalyst, which can introduce acetynyl into the benzene ring, thereby synthesizing the target product 1-chloro-4-ethynylbenzene.
Furthermore, it is also feasible to react with p-chlorophenyl lithium reagent with acetylene halide. Lithium p-chlorophenyl can be prepared from p-chlorobrombenzene and lithium metal in a low temperature and anhydrous and oxygen-free environment. This lithium reagent and acetylene halide through nucleophilic substitution reaction can efficiently obtain 1-chloro-4-ethynylbenzene. However, this process needs to strictly control the reaction conditions to prevent side reactions from occurring. All synthesis methods have their own advantages and disadvantages, and must be carefully selected according to actual needs and conditions to achieve the purpose of efficient and pure synthesis of 1-chloro-4-ethynylbenzene.
First storage, this compound should be stored in a cool and ventilated warehouse. Because it has certain chemical activity, high temperature or can cause reaction, it is essential to keep away from fire and heat sources. The temperature of the warehouse should be controlled within an appropriate range to prevent danger caused by excessive temperature. And it should be stored separately from oxidizing agents, acids, bases, etc., and must not be mixed. This is because 1-chloro-4-ethynylbenzene and other substances may have violent chemical reactions, even the risk of explosion. At the same time, the storage area should be equipped with suitable materials to contain leaks, so as to prevent accidental leakage and deal with them in time to avoid greater harm.
As for transportation, do not take it lightly. Be sure to ensure that the packaging is complete and well sealed before transportation. Packaging materials should be able to resist general vibration, collision and friction, so as not to cause material leakage. During transportation, the relevant transportation regulations must be strictly adhered to, and corresponding fire equipment and emergency treatment equipment should be equipped. Escort personnel must be familiar with the nature of the goods transported and emergency treatment methods, and pay close attention to the condition of the goods on the way. Vehicles should avoid densely populated and environmentally sensitive areas such as water sources and residential areas, in case of leakage, which will affect many people. When loading and unloading, the operator should load and unload lightly, and it is strictly forbidden to drop and heavy pressure, so as not to damage the packaging and cause danger. Therefore, when storing and transporting 1-chloro-4-ethynylbenzene, care should be taken everywhere to ensure safety.
If this compound escapes in the atmosphere, it is volatile or can migrate in the atmosphere. Its chlorine atoms may participate in photochemical reactions in the atmosphere, which may be potentially harmful to the ozone layer. Although the specific degree of its impact is difficult to determine due to the complex environment, the role of chlorine compounds in atmospheric chemical processes has always been of concern.
If it flows into the water body, 1-chloro-4-ethynylbenzene is hydrophobic, or adsorbed on suspended particles, and settles to the bottom. Contact with aquatic organisms, or biotoxic effects. The special structure may interfere with the normal biochemical reactions in organisms, causing growth and reproduction to be hindered. And may be enriched through the food chain, posing a threat to advanced organisms and even human health.
In the soil environment, its mobility may be limited, and it is mostly retained in the surface soil. However, it can affect the structure and function of soil microbial communities, inhibit some metabolic activities of microorganisms, and then interfere with the material cycle and energy conversion of soil ecosystems. Long-term accumulation may cause changes in soil fertility, affecting vegetation growth.
In summary, 1-chloro-4-ethynylbenzene can cause a series of chain reactions in various environmental media, and there is a latent risk to the ecological balance. It is necessary to treat it with caution and strengthen monitoring and control to ensure the safety of the environment.
In terms of reactivity, the chlorine atoms in this compound are connected to the benzene ring. Due to the electronic effect of the benzene ring, the activity of chlorine atoms is different. The conjugate system of the benzene ring reduces the electron cloud density of chlorine atoms, which is more difficult to leave than the halogen atoms in halogenated alkanes. However, under certain conditions, nucleophilic substitution reactions can still occur. In case of strong nucleophilic reagents, such as sodium alcohol, ammonia, etc., the chlorine atoms can be replaced by nucleophilic reagents to generate corresponding substitution products. In this process, the nucleophilic reagent attacks the carbon atom connected to the chlorine atom, and the chlorine atom leaves with a pair of electrons, thus forming a new carbon-nucleophilic bond.
The presence of ethynyl groups adds another activity to this compound. Ethynyl groups are unsaturated groups with electron-rich properties and can undergo various addition reactions. If they interact with bromine water, electrophilic addition can occur, and bromine atoms are gradually added to the carbon-carbon triple bond of the ethynyl group to form a dibromoolefin intermediate, which can then form tetrabromoproducts. Under the action of a suitable catalyst with hydrogen, a hydrogenation reaction can occur, and the control conditions can selectively add the carbon-carbon triple bond to the carbon-carbon double bond, or completely hydrogenate to a single bond.
In addition, the benzene ring in 1-chloro-4-ethynylbenzene can undergo aromatic electrophilic substitution. Because the chlorine atom is an ortho-para-site group, although the electron cloud density of the benzene ring is reduced, the reactive activity is slightly weaker than that of benzene, but the electrophilic reagents still tend to attack the ortho and para-sites of the chlorine atom. If the mixed acid of nitric acid and sulfuric acid interacts with nitric acid, a nitrification reaction can occur, and the ortho or para-site of the chlorine atom can be
In addition, the ethynyl group of this compound can also participate in metal-catalyzed coupling reactions. In the presence of palladium, copper and other metal catalysts and ligands, it can be coupled with halogenated hydrocarbons, borates, etc., to form carbon-carbon bonds, resulting in more complex organic compounds, which are widely used in the field of organic synthesis. In short, the chemical properties of 1-chloro-4-ethynylbenzene are rich and diverse, providing many possibilities for organic synthesis and chemical research.
Next step, chlorobenzene is converted into Grignard reagent. Take chlorobenzene and react with magnesium in an anhydrous ether environment to form phenyl magnesium chloride, which is Grignard reagent. The reaction formula is: $C_ {6} H_ {5} Cl + Mg\ xrightarrow [] {anhydrous ether} C_ {6} H_ {5} MgCl $.
Furthermore, the Grignard reagent is used to react with acetylene-related compounds. Generally, acetylene is reacted with sodium metal to obtain sodium acetylene. $C_ {2} H_ {2} + 2Na\ xrightarrow [] {} C_ {2} Na_ {2} + H_ {2} $. Then, phenyl magnesium chloride is reacted with sodium acetylene to form 1-chloro-4-ethynylbenzene. The reaction formula is: $C_ {6} H_ {5} MgCl + C_ {2} Na_ {2}\ xrightarrow [] {} C_ {6} H_ {4} ClC\ equiv CH + MgClNa $.
Another common synthesis method is to use p-chlorotoluene as the starting material. The side chain halogenation of p-chlorotoluene is first carried out. If bromine is reacted under light conditions, the hydrogen on the methyl group is replaced by bromine to obtain p-chlorobenzyl bromide. $C_ {6} H_ {4} ClCH_ {3} + Br_ {2}\ xrightarrow [] {light} C_ {6} H_ {4} ClCH_ {2} Br + HBr $. Subsequently, p-chlorobenzyl bromide is reacted with acetylene under alkaline conditions. Strong bases such as potassium hydroxide are often used as reaction conditions to induce nucleophilic substitution reactions between the two, resulting in the generation of 1-chloro-4-ethynylbenzene. Although the steps of this synthesis path are different, they are all common methods for obtaining 1-chloro-4-ethynylbenzene.
In the field of organic synthesis, this compound is often a key raw material. Due to the properties of chlorine atoms and ethylene groups, complex organic molecular structures can be constructed through various chemical reactions. For example, in nucleophilic substitution reactions, chlorine atoms can be replaced by many nucleophiles, thereby introducing different functional groups. This process is like building a delicate castle, and each step of the reaction adds to the building blocks, creating organic products with different structures, laying the foundation for the development of subsequent fields such as medicinal chemistry and materials science.
In the field of medicinal chemistry, 1-chloro-4-ethynylbenzene is also important. With it as a starting material, derivatives obtained through multi-step reactions may have potential biological activities. Scientists are like those seeking treasure, trying to discover new drugs with good pharmacological properties through modification and modification of their structures. For example, some derivatives may act on specific disease targets and contribute to human health and well-being.
In the field of materials science, its application should not be underestimated. Polymer materials synthesized by 1-chloro-4-ethynylbenzene may exhibit unique physical and chemical properties. For example, the polymer materials made of it may have good thermal stability, mechanical properties, etc. These materials are used in high-end fields such as aerospace and electronic equipment, such as strong armor, to provide stable and reliable performance support for related equipment and help technology take off.
When it comes to appearance, under room temperature and pressure, 1-chloro-4-ethynylbenzene is often colorless to pale yellow liquid, clear and transparent, and has a good texture. The shape of this color state is caused by factors such as its molecular structure and electron cloud distribution.
Its smell is slightly irritating, but not pungent. This pungent smell is derived from the chemical activity of chlorine atoms and ethynyl groups in the molecule, and the interaction between the two causes the compound to be reflected in the sense of smell.
When it comes to the boiling point, it is between 195 ° C and 197 ° C. This boiling point is due to the intermolecular force. The chlorine atoms present in the molecule can form a certain degree of dipole-dipole force due to their high electronegativity; while the unsaturated structure of the acetylene group also affects the intermolecular force. The synergistic effect of the two results in its specific boiling point.
In terms of melting point, it is roughly -12 ° C. The value of the melting point is closely related to the arrangement of the molecules. The shape and interaction mode of the molecules of the compound determine the energy required for it to change from solid to liquid at low temperatures, resulting in this melting point.
In terms of solubility, 1-chloro-4-ethynylbenzene is slightly soluble in water. This is because water is a polar molecule, and although the compound contains polar chlorine atoms, the main structure of ethynyl and benzene rings is non-polar. According to the principle of "similar miscibility", it is slightly soluble in water. However, it is soluble in many organic solvents, such as ethanol, ether, dichloromethane, etc. In such organic solvents, the intermolecular forces can be matched, resulting in good solubility.
The density is about 1.18g/cm ³, and the value of this density is determined by the molecular weight and the degree of intermolecular packing. The structure composed of benzene ring, chlorine atom and ethynyl group is arranged and combined in space to give the compound this specific density property.
The physical properties of 1-chloro-4-ethynylbenzene are derived from its unique molecular structure, and the various properties are interrelated to outline the physical properties of this compound.
First, it should be stored in a cool place. Intense high temperatures can easily cause the molecular activity of the compound to increase greatly, or cause chemical reactions, cause it to deteriorate, or even cause danger. Therefore, a cool environment can reduce its reactivity and maintain its chemical stability.
Second, a dry place is indispensable. In moisture, many compounds are easy to react with water, and 1-chloro-4-ethynylbenzene may also react with water, which may hydrolyze or cause other adverse reactions. Therefore, drying can protect it from water intrusion.
Third, it needs to be placed in a well-ventilated place. If the storage space is poorly ventilated, the volatile gas of the compound will accumulate, which may not only endanger the health of the stored person, but also reach a certain concentration. In case of serious accidents such as open fire or static electricity, or explosion, good ventilation can disperse the volatile gas and reduce the risk.
Fourth, it should be kept away from fire sources and oxidants. 1-Chloro-4-ethynylbenzene may be flammable. If the fire source is close, it is easy to ignite and cause a fire. The oxidant is easy to oxidize with the compound, or cause a violent reaction, which endangers safety, so it must be kept away.
Fifth, it should be stored in a specific container. A container that can withstand the chemical properties of the compound, does not react with it, and has good sealing, anti-leakage and volatilization, such as some special glass bottles or plastic bottles, depending on its chemical properties.
In conclusion, the storage of 1-chloro-4-ethynylbenzene must be cool, dry, ventilated, away from fire-source oxidants, and in a suitable container to ensure its safety and stability and avoid accidents.

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