4-Iodophenylboronic acid is an organic compound with CAS 5122-99-6 and molecular formula C6H6BINO2. It usually appears as a solid white to light yellow. Its color may vary depending on purity or sample batch. It has good water solubility and can be dissolved in most organic solvents, such as methanol, ethanol, acetone, etc. However, in polar solvents such as acetonitrile or DMF, their solubility may be higher. The molecular structure contains an iodine atom, a benzene ring, and a boronic acid group.
Among them, the boronic acid group is a polar group containing boron atoms, which gives the compound a certain polarity. The iodine atom, as a non-polar group, is connected to its benzene ring, giving the entire molecule an asymmetric distribution of electron clouds. It is brittle and easily crushes into powder. When grinding or cutting it, careful handling is necessary to avoid damaging the sample. It is a reactive compound. For example, it can react with various metal ions or functional groups. These reactions typically involve the formation of coordination or covalent bonds and the generation of corresponding metal complexes or derivatives.
|
|
|
|
C.F |
C6H6BIO2 |
|
E.M |
248 |
|
M.W |
248 |
|
m/z |
248 (100.0%), 247 (24.8%), 249 (6.5%), 248 (1.6%) |
|
Elemental Analysis |
C, 29.08; H, 2.44; B, 4.36; I, 51.21; O, 12.91 |
4-Iodophenylboronic acid can be used for surface functionalization modification to improve the surface and interface properties of materials. For example, it can be used as a coupling agent for functional modification of glass, silicon-based materials, and metal surfaces to improve their wettability, corrosion resistance, and biocompatibility.
It has shown significant application potential in surface functionalization modification, bringing important innovations to the fields of materials science and engineering.
As an efficient surface modifier, it can significantly improve the surface and interface properties of materials, providing new functional characteristics for various substrates such as glass, silicon-based materials, metals, etc.
Specifically, it can be used as a coupling agent to tightly bond with the surfaces of these substrates through chemical bonding, thereby endowing them with new surface functions without changing the properties of the material itself. For example, it can improve the wettability of materials, making the liquid more evenly spread on the surface of the material, which is crucial for applications such as coatings, inks, adhesives, etc.
At the same time, it can enhance the corrosion resistance of materials by forming a protective film on the surface of the material, effectively preventing corrosive media from corroding the material and extending its service life.
For thin film preparation: Through the Langmuir Blodgett method, ordered Langmuir monolayers and Langmuir Blodgett multilayer films can be prepared using p-Iodophenylboromic Acid. These thin films have unique structures and optoelectronic properties, and have potential application value in fields such as optoelectronic devices, sensors, and energy conversion.
Used for preparing organic thin film solar cells
Organic thin film solar cells are a new type of solar cell with advantages such as low cost, flexible manufacturing, and solution processing. P-Iodophenylboromic acid, as an excellent electron acceptor material, is widely used in the preparation of organic thin film solar cells. During the preparation process, p-Iodophenylboromic acid can form ordered molecular aggregates with aromatic electron donor materials through π - π interactions and Lewis acid-base interactions.
This type of molecular aggregate has excellent electron transfer performance and tunable optoelectronic properties, which helps to improve the photoelectric conversion efficiency and stability of solar cells.
In addition, p-Iodophenylboromic acid can also introduce other functional groups such as alkyl and alkoxy groups through molecular design to further optimize the electronic structure and properties of the material. This versatility makes p-Iodophenylboromic acid an ideal candidate material in the field of organic thin film solar cells.
Used for preparing optoelectronic functional thin films
Photoelectric functional thin film is a thin film material with photoelectric conversion function and stable photoelectric performance. P-Iodophenylboromic acid, as a type of optoelectronic functional material, is widely used in the preparation of optoelectronic functional films.
During the preparation process, p-Iodophenylboromic acid can interact with components such as electron transport materials and semiconductor materials to form stable complexes or non covalent bond interactions, thereby achieving the regulation and optimization of optoelectronic functions.
This thin film material has high photoelectric conversion efficiency and stability, and can be applied in fields such as solar cells, photodetectors, and photodiodes. In addition, by combining and optimizing with other functional materials, the performance and application range of optoelectronic functional films can be further enhanced. For example, combining p-Iodophenylboromic acid with other organic small molecules or polymer materials can produce photoelectric sensors and switches with high sensitivity and fast response. These optoelectronic functional thin film materials have broad application prospects in fields such as optical communication, information processing, and biomedical engineering.
Used for preparing biocompatible films
Biocompatible film is a thin film material used in biological tissue engineering and biomedical engineering, with excellent biocompatibility and chemical stability. P-Iodophenylboromic acid, as a material with good biocompatibility, is widely used in the preparation of biocompatible films.
During the preparation process, p-Iodophenylboromic acid can be chemically modified and molecular designed to introduce other functional groups, such as amino and carboxyl groups, to enhance its interaction and biocompatibility with biological tissues. This thin film material can serve as a substrate for cell growth and attachment in biological tissue engineering, promoting cell proliferation and differentiation. Meanwhile, due to its good chemical stability and corrosion resistance, it can also be used in the manufacturing of medical devices and drug carriers.
The laboratory synthesis method of 4-Iodophenylboronic acid typically involves the following steps:
C6H5B(OH)2 + NaI + NaOH → C6H5B(OH)2-Na + I-Na
C6H5B(OH)2-Na + I-Na → C6H5B(OH)2 + NaOH + NaCl
C6H5B(OH)2 + H2O → C6H5B(OH)2 · H2O + NaOH
C6H5B(OH)2 · H2O + H2O → C6H5B(OH)2 + H2O2
Before conducting synthesis, it is necessary to prepare the required reagents and equipment. The required reagents include sodium iodide, phenylboronic acid, sodium hydroxide, methanol, etc. The equipment includes a stirrer, condenser, drip device, and rotary evaporator.
Dissolve phenylboronic acid in methanol to prepare a benzylboronic acid methanol solution.
Dissolve sodium iodide in water to prepare an aqueous solution of sodium iodide.
Mix the prepared benzylboronic acid methanol solution and sodium iodide aqueous solution together, add an appropriate amount of sodium hydroxide, and stir evenly.
Heat the mixture to reflux state, maintain the temperature at around 100 ° C, and react for a period of time (such as 1-2 hours) until the phenylboronic acid completely reacts.
Cool the reaction solution to room temperature, pour the mixture into a beaker, and use a rotary evaporator to evaporate the solvent to obtain the crude product.
Recrystallize the crude product with methanol to obtain pure 4 Iodophenylboronic acid crystals
(1) Filter the crude product to remove unreacted phenylboronic acid and other impurities.
(2) Recrystallize the filtered product with methanol to obtain pure 4 Iodophenylboronic acid crystals.
(3) Dry the crystallized product to obtain dry 4-Iodophenylboronic acid powder or crystals.
Quantitative nuclear magnetic resonance (qnmr)
Quantitative nuclear magnetic resonance (qNMR) is a quantitative analysis method based on the principle of nuclear magnetic resonance. It has the advantages of no need for standard substances, simple operation and accurate results, and is suitable for the purity detection of 4-iodobenzoboric acid.
Detection Principle
NMR achieves quantitative analysis by comparing the intensities of different absorption peaks in nuclear magnetic resonance spectra. For a definite proton, its integral area is proportional to the molar concentration. When detecting the purity of 4-iodobenoboric acid, it is necessary to first determine the integral area of its characteristic peak, the number of protons corresponding to this peak, the sample mass, the molar mass and the purity and other parameters.
At the same time, select the appropriate internal standard and determine its corresponding parameters. The purity of 4-iodobenzoboric acid can be obtained by calculating the ratio of the integral area of the characteristic peaks of the sample and the internal standard, the ratio of the number of protons, the ratio of the mass and the ratio of the molar mass, etc.
Inspection Process
Sample preparation
Use an ultramicro balance to accurately weigh the 4-iodobenzoboric acid sample and the standard substances (internal standards) for qNMR, ensuring that the weighed mass is greater than the minimum weighing value. Completely dissolve the sample and internal standard in an appropriate deuterated solvent, such as deuterated chloroform, and be careful to avoid overlapping of the signal of the deuterated reagent with that of the object being analyzed.
NMR detection
Transfer the sample solution to the nuclear magnetic resonance tube, set appropriate NMR detection conditions, such as a 1-hour resonance frequency above 400MHz, a digital resolution below 0.25Hz, a pulse Angle of 90°, and a delay time of more than 60 seconds, etc., conduct NMR detection and record the spectrum.
Data analysis
Perform phase correction, baseline correction and other processing on the spectrum, and select protons with less interference, better peak shapes and stable baselines for integration. According to the qNMR calculation formula, combined with the relevant parameters of the sample and the internal standard, the purity of 4-iodobenzoboric acid was calculated.
I. Early Foundation of Organoboron Compounds (Mid-to-Late 19th Century)
Research on organoboron compounds began in 1860. British chemist Edward Frankland first synthesized and isolated an alkylboronic acid derivative - ethylboronic acid, pioneering the exploration of organoboron chemistry.
In 1880, A. Michaelis and P. Becker successfully synthesized phenylboronic acid, extending boronic acid research into the aromatic field and laying a core foundation for the development of substituted phenylboronic acids.
During this period, organoboron compounds were merely regarded as chemical curiosities, featuring harsh synthesis conditions, low yields, and untapped application value.
II. Synthesis and Emergence (Mid-20th Century)
In the mid-20th century, breakthroughs in synthetic technologies such as Grignard reagents and organolithium reagents greatly improved the synthesis efficiency of substituted phenylboronic acids.
As an important haloarylboronic acid, 4-Iodophenylboronic acid was successfully synthesized in the 1950s–1960s. Its classic synthetic route adopts 1,4-diiodobenzene as the raw material, which undergoes lithiation with n-butyllithium, reacts with triisopropyl borate, and is finally obtained via hydrolysis.
This method remains the mainstream laboratory preparation protocol to this day. At that time, it was mainly used as an organic synthesis intermediate for constructing boron-containing functional molecules, without large-scale industrial application.
III. Rise of Applications and Establishment of Value (Late 20th Century to Present)
After the 1990s, research on it reached an inflection point. In 1996, it was discovered to act as a potent enhancer for the horseradish peroxidase (HRP)-catalyzed luminol chemiluminescence system, greatly enhancing luminescence intensity and detection sensitivity, and promoting its wide application in clinical immunoassay and biosensing fields.
In 2010, the Suzuki–Miyaura coupling reaction was awarded the Nobel Prize in Chemistry. As a difunctional monomer containing both iodine atom and boronic acid group, it has become a key building block for constructing conjugated polymers (e.g., poly(phenylene)), complex drug molecules and organic functional materials.
Its synthetic processes have been continuously optimized, and industrial production has gradually matured. Since then, it has evolved from a niche intermediate into an important chemical in organic synthesis, materials science, biomedicine and related fields.
FAQ
1. What is the specific influence of the spatial steric hindrance of the iodine atom on the metalation step in the Suzuki coupling reaction?
+
-
Compared to other halogens, the iodine atom has a larger volume, which may cause a slight change in the planarity of the benzene ring, thereby affecting the coordination with the palladium catalyst and the subsequent rate of formation of the aryl-palladium bond. In some substrates, this may lead to fluctuations in the coupling efficiency.
2. How stable is the ester exchange reaction of this compound with the ortho-diphenolic group in a non-catalytic environment (such as a physiological pH buffer solution)?
+
-
The strong electron-withdrawing property of iodine enhances the acidity of boronic acid, making it more likely to form reversible cyclic esters with diols under near-neutral conditions. However, this bond is also relatively sensitive to hydrolysis, and in biological applications (such as sugar sensors), dynamic equilibrium needs to be considered.
3. Does a specific packing pattern exist in the solid state that is driven by the interaction between iodine atoms or the interaction between iodine and π bonds?
+
-
Single crystal diffraction reveals that the molecules may form specific supramolecular assemblies through weak iodine-Iodine interactions or interactions between iodine atoms and the π electron clouds of adjacent benzene rings. This will affect its crystalline form and solubility.
4. Under light conditions, could the carbon-iodine bond be cleaved and result in free radical side reactions?
+
-
The bond energy of the carbon-iodine bond is relatively low. Under strong ultraviolet light irradiation or the presence of free radical initiators, it may undergo cleavage to form phenyl radicals, which in turn may trigger unnecessary polymerization or react with solvents, thereby affecting its stability in photochemical synthesis.
Hot Tags: 4-iodophenylboronic acid cas 5122-99-6, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, Sodium Dodecyl Aulfate Powder CAS 151 21 3, Monostearin, Dodecyltrimethylammonium chloride, Sodium Isopropyl Xanthate SIPX , Hypophosphorous Acid Solution CAS 6303 21 5, 2 2 Dithiobis benzothiazole CAS 120 78 5