Application examples of 4-hydroxymethylphenylboronic acid_Industrial additives

Background and overview of application examples of 4-hydroxymethylbenzeneboronic acid

4-Hydroxymethylbenzeneboronic acid is a boric acid derivative. Boronic acid derivatives are widely used in organic synthesis for the formation of carbon-carbon bonds. In the Suzuki coupling, aryl halides and aryl or vinyl borates or boronic acids are coupled using Pd(PPh₃)₄.

Application examples of 4-hydroxymethylbenzeneboronic acid

Examples of application of 4-hydroxymethylbenzeneboronic acid Application 1,

4-Hydroxymethylphenylboronic acid can be used to prepare 4-amino-pyrimidonazaheterocyclic derivatives with the following structure, which are BTK inhibitors. BTK activates FcγR signaling through immune complexes in myeloid cell function. In macrophages, BTK inhibition can block the INF-α, IL-1β and IL-6 products induced by Fc-thiopheneboronic acid RIII, and block BCR-dependent B cell proliferation through NF-kB activation. This is the role of BTK in macrophages. There is strong evidence for the treatment of autoimmune diseases, including rheumatoid arthritis and systemic erythematosus. In addition, BTK has been confirmed by many parties as a target for the treatment of lymphoma-related diseases.

Examples of application of 4-hydroxymethylbenzeneboronic acid Application 2.

CN202010073465.5 reported that 4-hydroxymethylphenylboronic acid can be used to prepare a porcelain-resistant ablation coating, including the following components and mass percentages, silicone resin 55% to 65%, curing agent 8% ~15%, filler 20% ~ 35%, additive 0.1% ~ 0.5%.

The preparation method of the coating includes the following steps:

(1) Add the measured mixture of phenyltriethoxysilane, phenylboronic acid and 4-hydroxymethylphenylboronic acid, absolute ethanol and acetic acid into a reflux condenser, magnetic stirring paddle, thermometer, thermoelectric In the reaction kettle coupled with the constant pressure dropping funnel, first raise the temperature to 65°C. After the mixture of phenylboric acid and hydroxymethylbenzene boric acid is completely dissolved, add an appropriate amount of deionized water and acetic acid to the constant pressure dropping funnel. And complete the dropwise addition within 2 hours; continue to raise the temperature to 100°C, react for 5 hours, then distill under reduced pressure, transfer it to a vacuum oven, and keep it at 120°C for 2 hours to obtain a silicone prepolymer. Among them, the molar ratio of phenyltriethoxysilane to the mixture of phenylboronic acid and hydroxymethylbenzeneboronic acid is 1:2.0. Next, the silicone prepolymer is modified with aminochloropyridine using epoxy resin, and the active hydroxyl group or alkoxy group of the silicone prepolymer is used to perform a condensation reaction with the hydroxyl group of the epoxy resin to prepare the silicone resin. According to the weight percentage, the silicone prepolymer is 35%, the o-cresol type novolac epoxy resin is 15%, the reaction temperature and reaction time are 100°C and 5h respectively, and a silicone resin is prepared.

(2) Place the silicone resin, fillers (hollow phenolic microbeads, talc, montmorillonite, calcium carbonate, zirconium oxide), and additives (polyamide dispersants, acrylic leveling agents) Put the mixture in a container and mix, stir in a high-speed mixer at a speed of r/min for 45 minutes, and further use a planetary ball milling method to ball mill at a speed of r/min for 60 minutes. The high-temperature resistant heat-insulating coating can be obtained as component A and component B. The curing agent is an alicyclic polyamine.

(3) Preparation of ablation-resistant coating: Weigh a certain amount of component A and component B, mix at high speed and stir evenly. After adjusting to the appropriate construction viscosity, spray evenly on the surface of the metal substrate, and apply the The porcelain-resistant ablation coating can be obtained after the coating is treated at 70°C for 10 minutes.

References

[1] [Chinese invention] CN201711448020.5 4-Amino-pyrimidozaheterocyclic derivative and its preparation method and use

[2] [Chinese invention] CN202010073465.5 A porcelain-resistant ablation-resistant coating and its preparation method