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What is the chemical structure of (s) -1- (5-fluoro-2-iodophenyl) ethan-1-ol?
The chemical structure of (s) -1 - (5-fluoro-2-iodophenyl) ethanol is actually composed of a specific combination of atoms, which is arranged in a unique space. Its core is an ethanol structure, that is, one ethyl group is connected to one hydroxyl group. At position 1 of the ethanol structure, there is a phenyl group, which is a phenyl ring structure with a ring structure composed of six carbon atoms. It is particularly crucial that there are fluorine atoms at position 5 of the phenyl group, and iodine atoms at position 2. The word " (s) " before the overall structure indicates that the compound has a specific stereochemical configuration, which is a chiral compound. In space, the atomic arrangement of the molecule presents a specific enantiomeric form, expressed in the (s) configuration. Its structure determines the specific physical and chemical properties of the compound, which is of great significance in many fields such as organic synthesis and medicinal chemistry.
What are the main physical properties of (s) -1- (5-fluoro-2-iodophenyl) ethan-1-ol?
(S) -1 - (5-fluoro-2-iodophenyl) ethanol, this substance has optical rotation, because it contains chiral carbon atoms, exhibits optical activity, and can rotate the vibration plane of polarized light, turning left or right under specific conditions.
When it is at room temperature and pressure, it is generally liquid. It has a certain volatility and can be slowly volatilized in air.
In terms of solubility, its molecules contain hydroxyl groups, with a certain polarity, slightly soluble in water, because hydroxyl groups can form hydrogen bonds with water molecules; it has good solubility in organic solvents, such as miscibility with common organic solvents such as ethanol, ether, acetone, etc.
The melting point and boiling point of this substance are affected by intermolecular forces. In addition to van der Waals forces, hydroxyl groups can also form hydrogen bonds between molecules, resulting in enhanced intermolecular forces. Its melting point and boiling point are higher than those of some compounds with similar structures but no hydroxyl groups. The specific values are determined according to accurate experiments.
The density is usually higher than that of water, and it will sink to the bottom when placed in water. Its chemical stability is better under certain conditions, but due to the iodine atom, in a specific chemical reaction or environment, the iodine atom may undergo substitution and other reactions, resulting in changes in its chemical properties.
In which chemical reactions is (s) -1- (5-fluoro-2-iodophenyl) ethan-1-ol commonly used as a feedstock?
(S) -1 - (5-fluoro-2-iodophenyl) ethanol is often used as a key raw material in many organic synthesis reactions. Due to its unique structure, it can exhibit different activities and reactive properties in many chemical reactions.
In the halogenation reaction, this compound can react with various nucleophilic reagents by virtue of the presence of iodine and fluorine atoms on the benzene ring. For example, when it encounters an alcohol salt nucleophilic reagent, the iodine atom can be replaced by an alkoxy group to generate phenethyl alcohol ether compounds with different substituents. This reaction is commonly used in the synthesis of organic molecules with specific functional groups.
In the field of reduction reactions, the hydroxyl groups of the compound can be further reduced and converted into alkyl groups under suitable reduction conditions, thereby preparing halogenated phenylethanes with simpler structures. For example, strong reducing agents such as lithium aluminum hydride can efficiently achieve this conversion, which plays an important role in organic synthesis for the construction of specific carbon skeleton structures.
In addition, in the reaction of building carbon-carbon bonds, (s) -1 - (5-fluoro-2-phenyliodine) ethanol can also play a key role. For example, with the help of palladium-catalyzed cross-coupling reaction, iodine atoms can be coupled with carbon-containing nucleophiles, such as Suzuki coupling reaction with alkenyl borate esters, which can generate phenyl-ethanol derivatives containing alkenyl substitutions, laying the foundation for the synthesis of organic materials and bioactive molecules with conjugated structures.
In summary, (s) -1 - (5-fluoro-2-iodophenyl) ethanol, with its unique structure, is a commonly used and important raw material in many types of organic chemical reactions such as halogenation, reduction, and carbon-carbon bond construction, providing rich possibilities and diverse path choices for the research and practice of organic synthetic chemistry.
What are the synthesis methods of (s) -1- (5-fluoro-2-iodophenyl) ethan-1-ol?
The method of synthesizing (S) -1- (5-fluoro-2-iodophenyl) ethanol is the key to organic synthetic chemistry. This compound has important uses in medicine, materials and other fields. The synthesis method is described in detail below.
First, 5-fluoro-2-iodobenzaldehyde is used as the starting material, and the target product can be prepared by asymmetric reduction reaction. In this method, the selection of appropriate reducing agents and chiral catalysts is crucial. For example, a catalytic system composed of sodium borohydride and chiral ligands can be used. Sodium borohydride is a commonly used reducing agent with mild reaction conditions and high selectivity. Chiral ligands work synergistically with sodium borohydride to induce the reaction to produce products of a specific configuration. This reaction is often carried out at low temperature and in an anhydrous environment to ensure the high efficiency and selectivity of the reaction.
Second, 5-fluoro-2-iodobenzoic acid can also be used as a starting material, first converted into the corresponding acid chloride, and then reacted with Grignard reagent, and then reduced to obtain (S) -1- (5-fluoro-2-iodophenyl) ethanol. This path requires attention to the control of the conditions of each step of the reaction. When preparing acid chloride, a suitable chlorination reagent, such as dichlorosulfoxide, needs to be selected, and the reaction needs to be in an anhydrous environment to avoid hydrolysis of acid chloride. Grignard reagent reaction requires a high degree of anhydrous and anoxic reaction system to ensure the activity of Grignard reagent. In the subsequent reduction step, a suitable reducing agent can be selected according to the specific situation, such as lithium aluminum hydride.
Third, a synthetic route based on the nucleophilic substitution reaction of halogenated aromatics can also be designed. First, the 5-fluoro-2-iodobenzene halogen is reacted with a suitable nucleophilic reagent, the carbon chain containing hydroxyl groups is introduced, and then the chiral induction step is carried out to finally obtain the target product. In this process, the selection of nucleophilic reagents, the optimization of reaction conditions, and the method of chiral induction all need to be carefully considered.
The above methods have their own advantages and disadvantages. In actual synthesis, it is necessary to comprehensively weigh factors such as the availability of raw materials, cost, difficulty of reaction conditions, and the purity and configuration requirements of the target product to choose the optimal synthesis path.
What are the applications of (s) -1- (5-fluoro-2-iodophenyl) ethan-1-ol in industrial production?
(S) -1- (5-fluoro-2-iodophenyl) ethane-1-ol is used in industrial production and has a wide range of uses.
First, in the field of pharmaceutical synthesis, it is often a key intermediate. In the process of many drug development, its structure needs to be integrated into the target drug molecule through specific chemical reactions. For example, for some anti-cancer drugs with unique therapeutic effects, the craftsmen have carefully designed the reaction path and used (s) -1- (5-fluoro-2-iodophenyl) ethane-1-ol as one of the starting materials. Through a series of delicate operations such as halogenation reaction and substitution reaction, the molecular framework of the drug is gradually built, laying the foundation for the creation of anti-cancer drugs.
Second, in the field of materials science, it also has outstanding performance. The preparation of some functional materials involves its participation. For example, when preparing organic materials with specific optical properties, (s) -1- (5-fluoro-2-iodophenyl) ethane-1-ol can endow materials with unique light absorption and emission characteristics due to its special atoms such as fluorine and iodine. Material craftsmen fine-tune the reaction conditions to polymerize or composite with other organic monomers to obtain materials that meet specific optical needs, which are used in cutting-edge fields such as optical displays and optoelectronic devices.
Third, in the research and exploration of organic synthetic chemistry, (s) -1- (5-fluoro-2-iodophenyl) ethane-1-ol is like a key, opening the door to many novel reaction paths. Chemists use it as a substrate to explore new catalytic systems and reaction mechanisms, promote the progress of organic synthesis methodologies, and provide the possibility for the efficient construction of more complex organic molecules.
