Preparation and application of 2-formylphenylboronic acid_Industrial additives

Preparation and application background and overview of 2-formylphenylboronic acid pyridinedicarboxylic acid

2-Formylbenzeneboronic acid is an aldehyde phenylboronic acid. In recent years, the use of Suzuki coupling reaction for the synthesis of key drug intermediates has become increasingly common. For example, p-aldehyde phenylboronic acid is used in the synthesis of the powerful protease inhibitor atazanavir, a new drug on the market.

Preparation and application of 2-formylphenylboronic acid

Preparation and application of 2-formylphenylboronic acid Synthesis of o-bromophenylboronic acid trimer:

In a 1L three-necked flask equipped with a reflux water separation device, add o-bromobenzoic acid (201 grams, 1.0 mol) and 600 ml of toluene, and heat to reflux and water separation. When the system separates about 17.5-18.0 grams of water , and stop the reaction when there is no more water in the system to continue to separate. After cooling down, the heptane is distilled until no liquid flows, and a crude m-bromobenzoic acid trimer is obtained, which at this time contains about 5-10% toluene. You can go directly to the next step of the reaction.

Preparation and application of 2-formylphenylboronic acid Synthesis of 2-formylphenylboronic acid:

Under nitrogen protection, add 600 ml of anhydrous tetrahydrofuran to the o-bromophenylboronic acid trimer obtained above and dissolve it evenly, transfer it to a 2L three-necked bottle, and then add dimethylformamide (87.7 g, 1.2 mol) . Then the system was cooled to -70°C to -80°C, and 520 ml (1.3 mol) of 2.5M n-butyllithium hexane solution began to be slowly added dropwise. During the addition process, the maximum temperature was controlled not to exceed -70°C, and the temperature was maintained after the addition was completed. Continue to stir the reaction for 1-3 hours, then naturally raise to room temperature and stir for 3-5 hours. After the TLC detection reaction is completed, cool the system to 0°C, add 15% hydrochloric acid aqueous solution to quench the reaction, adjust the pH to 1-2 and continue stirring at room temperature for 3-5 hours to ensure complete hydrolysis of the trimer. The reaction solution was distilled. After the organic solvent was distilled, a solid precipitated. It was filtered and recrystallized from toluene to obtain 93.0 g of light gray solid 2-formylphenylboronic acid. HPLC: 99.0%. The total yield of the two steps was 62%.

Preparation and application of 2-formylphenylboronic acid

CN201710690352.8 reports the self-assembly of diphenol compounds and 2-formylphenylboronic acid and its application as a fluorescent probe. The invention relates to the self-assembly formed by two diphenol compounds and 2-formylphenylboronic acid respectively. The assembly is used as a fluorescent probe. The diphenol compound is added with 2-formylphenylboronic acid in phosphate buffer to form a self-assembly system, which can be used for the quantitative detection of free radical hypochlorous acid and peroxynitrite. This type of probe The advantage is that the self-fluorescence is weak, and the fluorescence is significantly enhanced only after interacting with the substance to be measured. Compared with other free radical detection fluorescence extraction and quenching probes, this type of assembly probe has higher Signal-to-noise ratio, fast, sensitive, simple and efficient.

CN201610061463.8 reports a sugar-responsive supramolecular gel with a G-quadruplex structure, centered on the sugar response of 2-formylphenylboronic acid, using the ortho-diol structure of guanine nucleoside and its A dynamic covalent boron ester bond is formed, and then a dynamic imine bond is formed through the primary amine in tris(2-aminoethyl)amine and the aldehyde group of 2-formylphenylboronic acid. The bases of the guanine nucleoside are between It forms a G-tetrad square structure under the stabilization of potassium ions; it can be used to detect the release effect of melanin in glucose solutions and acidic solutions. The advantages of the present invention are: the gel prepared by this method is stable, has high strength, has good sugar responsiveness and can load a large amount of large/small molecule gel; the raw materials involved in the preparation method are simple and can be used without complicated synthesis steps. Preparing supramolecular hydrogels from small molecules has low cost and simple production process. The products can be stored for a long time without deterioration. The raw materials have low toxicity and are easy to promote and apply.

Chromium picolinate

References on the preparation and application of 2-formylphenylboronic acid

[1][China invention, China invention authorization] CN201510321210.5 A method for preparing aldehyde phenylboronic acid

[2] CN201710690352.8 Self-assembly of diphenol compounds and 2-aldehyde phenylboronic acid and its application as a fluorescent probe

[3] CN201610061463.8 A sugar-responsive supramolecular gel with a G-quadruplex structure and its preparation method

TAG: 2-formylphenylboronic acid, o-bromophenylboronic acid trimer, application

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