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What is the chemical property of Benzene, 1-Iodo-2- (Trifluoromethyl) -
1-Iodine-2- (trifluoromethyl) benzene has unique chemical properties, including the characteristics of benzene ring and specific substituents.
The benzene ring is stable, an aromatic compound with a large π bond and a planar hexagonal structure. In this compound, the electron cloud distribution of the benzene ring is changed by the substitution of iodine atom and trifluoromethyl.
The iodine atom has a large atomic radius and lone pair of electrons. From the perspective of electronic effect, it has an electron-absorbing effect (-I effect). Because its electronegativity is larger than that of carbon, the electron cloud density of the benzene ring decreases, especially at the adjacent and para-sites. However, the solitary pair electrons of iodine can be conjugated with the large π bond of the benzene ring to produce the electron-donor conjugation effect (+ C effect), but this effect is relatively weak. In general, iodine reduces the electron cloud density of the benzene ring and weakens the electrophilic substitution activity of the benzene ring.
Trifluoromethyl (-CF 🥰), due to the extreme electronegativity of the fluorine atom, has a strong electron-absorbing induction effect (-I effect), and no electron-donor conjugation effect. This group greatly reduces the electron cloud density of the benzene ring and further weakens the electrophilic substitution activity of the benzene ring. In synergy with the iodine atom, the electrophilic substitution activity of
In the electrophilic substitution reaction, due to the localization effect of iodine and trifluoromethyl, both are ortho-and para-localization groups. However, the strong electron-absorbing effect of trifluoromethyl makes the density of the ortho-electron cloud lower than that of the para-position, so the electrophilic reagents tend to attack the para-position more.
In addition, the carbon-iodine bond in this compound is relatively active, and the iodine atom can undergo nucleophilic substitution reaction. Due to the large tendency of iodine atoms to leave, under appropriate nucleophilic reagents and reaction conditions, iodine can be replaced to form new organic compounds. The existence of trifluoromethyl affects the polarity and spatial structure of the molecule, and also affects its physical properties such as boiling point and solubility. Due to the increase in molecular polarity, trifluoromethyl causes its boiling point to be relatively high, and its solubility in organic solvents also varies due to polarity changes.
What are the main uses of Benzene, 1-Iodo-2- (Trifluoromethyl) -?
1-Iodine-2- (trifluoromethyl) benzene has a wide range of uses. In the field of organic synthesis, it is often a key raw material.
First, it can be used to create special fluorine-containing compounds. Due to the presence of trifluoromethyl in the molecule, this group has unique electronic and spatial effects, resulting in special physical and chemical properties of the product. For example, in pharmaceutical research and development, the introduction of this structure can improve the biological activity, lipophilicity and metabolic stability of drugs, thereby enhancing the efficacy.
Second, in the field of materials science, it can be used as a monomer for the synthesis of fluorine-containing polymer materials. Materials polymerized from such monomers often have excellent chemical resistance, low surface energy and excellent electrical properties, and can be used to make special coatings, high-performance plastics, etc.
Third, in the field of pesticides, 1-iodine-2 - (trifluoromethyl) benzene can be used as a starting material for the synthesis of new pesticides. The synthesized pesticides, or due to the existence of trifluoromethyl, have stronger toxicity and selectivity to pests, and are environmentally friendly and degrade quickly.
Furthermore, in the synthesis of fine chemicals, it is often used as an intermediate to participate in multi-step reactions to prepare high-value-added fine chemicals, such as special fragrances, dyes, etc. Due to its unique structure, it can impart a unique color, aroma, or other functional characteristics to the product.
What is the synthesis method of Benzene, 1-Iodo-2- (Trifluoromethyl) -
To prepare 1-iodine-2 - (trifluoromethyl) benzene, the following method can be used.
Take o-trifluoromethylbenzoic acid as the starting material and react with it with an appropriate reagent, such as thionyl chloride ($SOCl_2 $). In this step, the chlorine atom in the thionyl chloride replaces the hydroxyl group of the benzoic acid to produce o-trifluoromethylbenzoyl chloride. This reaction needs to be carried out at an appropriate temperature and reaction environment to promote its complete conversion.
The obtained o-trifluoromethylbenzoyl chloride is then reacted with a reducing agent, such as lithium aluminum hydride ($LiAlH_4 $). Lithium aluminum hydride can reduce the carbonyl group of the acid chloride to methylene, so that o-trifluoromethylbenzyl alcohol can be obtained. This step needs to be handled with caution, because the high activity of lithium aluminum hydride requires strict reaction conditions.
o-trifluoromethylbenzyl alcohol is reacted with appropriate halogenating reagents, such as phosphorus triiodide ($PI_3 $). The iodine atom in phosphorus triiodide replaces the alcohol hydroxyl group, so that the target product 1-iodine-2 - (trifluoromethyl) benzene. This reaction also requires attention to the regulation of reaction conditions, such as temperature, reactant ratio, etc., to make the reaction smooth and improve the yield of the product.
Or it can be started by m-trifluoromethylaniline. The diazonium salt is formed by reacting with a diazonium reagent composed of sodium nitrite ($NaNO_2 $) and hydrochloric acid. The diazonium salt is extremely unstable and needs to be carried out at low temperature to prevent its decomposition. The resulting diazonium salt is then reacted with potassium iodide ($KI $), and the diazonium group is replaced by an iodine atom to obtain 1-iodine-2 - (trifluoromethyl) benzene. The control of conditions for the diazotization and substitution reactions in this path is extremely critical, which is related to the purity and yield of the product.
Benzene, 1-Iodo-2- (Trifluoromethyl) - What to watch out for when storing
1-Iodine-2- (trifluoromethyl) benzene, when storing, need to pay attention to many matters. This compound has unique characteristics, one of which is quite sensitive to environmental conditions. It should be stored in a cool, dry and well-ventilated place, due to moisture and high temperature or deterioration. Moisture may cause reactions such as hydrolysis, which will damage its chemical structure; high temperature may promote its decomposition, causing changes in composition, affecting its quality and utility.
In addition, because it contains groups such as iodine and trifluoromethyl, its chemical activity may be special. During storage, it should avoid contact with highly active substances, such as strong oxidizing agents and strong reducing agents. Strong oxidants meet with it, or trigger a violent oxidation reaction, causing the risk of combustion or even explosion; strong reducing agents may also cause uncontrollable reduction reactions, changing their chemical composition.
In addition, 1-iodine-2 - (trifluoromethyl) benzene may have certain toxicity and irritation. The storage place must ensure the safety of personnel, and clear warning signs should be set up to prevent accidental touch and ingestion. When taking it, you should also follow strict operating procedures and be equipped with protective equipment, such as gloves, goggles, etc., to prevent harm to the human body.
Again, the choice of storage container is also important. Materials that can withstand its chemical properties, such as specific glass or plastic materials, need to be used. The selected container should be well sealed to prevent volatilization and leakage. If a leak occurs, it will not only waste materials, but also pose a threat to the environment and personnel safety. Regular inspection of the integrity of the container and timely detection and treatment of potential leaks is appropriate.
Benzene, 1-Iodo-2- (Trifluoromethyl) - what impact does it have on the environment?
Benzene, 1-iodine-2 - (trifluoromethyl) This substance has a complex impact on the environment, so let me tell you one by one.
1-iodine-2 - (trifluoromethyl) Benzene contains special atoms such as fluorine and iodine, and its chemical stability is high. In the natural environment, the degradation process is slow, or it may remain for a long time. Once it enters the water body, it is easy to adsorb on suspended particles or sediment due to its hydrophobicity, posing a potential threat to aquatic ecosystems. It may affect the growth, reproduction and behavior of aquatic organisms, and interfere with their normal physiological functions.
In the atmospheric environment, 1-iodine-2- (trifluoromethyl) benzene may participate in photochemical reactions under conditions such as light, generating secondary pollutants and affecting air quality. And because of its physical properties such as vapor pressure, or long-distance transmission in the atmosphere, the scope of pollution is expanded.
The soil environment is also affected by it, because it is difficult to degrade, or accumulates in the soil, changing the soil physical and chemical properties, affecting the structure and function of soil microbial community, and then affecting plant growth and soil ecosystem balance.
And because of its certain toxicity, after biological ingestion, it may be enriched in organisms and transmitted through the food chain, threatening high nutrient level organisms and even human health. Therefore, benzene, 1-iodine-2-trifluoromethyl, and other substances should be treated with caution and environmental monitoring and control should be carried out to prevent them from causing serious and lasting harm to the environment.