3-Formylphenylboronic acid

Off-white Cryst

Separately, a three-necked flask having a capacity of 3 liters was charged with 154.8 ml of trimethyl borate and then with 915 ml of THF to prepare a solution of trimethyl borate in THF. The solution was agitated while a nitrogen gas flowed through the flask and the solution was cooled with ice. The ice-cooled THF solution was mixed with the Grignard reagent fed into the 3 liter flask through a stainless steel pipe. The resultant reaction mixture liquid was agitated for one hour while cooling with ice, and then further mixed with an aqueous sulfuric acid solution prepared from 30 ml of concentrated sulfuric acid and 480 ml of water. The temperature of the resultant admixture liquid was raised to room temperature and, then, the admixture liquid was agitated at this temperature for 2 hours. Thereafter, the agitation was stopped and the resultant reaction mixture liquid was left to stand in the ambient atmosphere for one night. The precipitate generated in the reaction mixture liquid was removed by filtration and the resultant filtrate was concentrated. The resultant concentration residue was mixed with water in a volume equal to that of the concentration residue, the resultant mixture liquid was agitated at room temperature for one hour. The resultant solid fraction was collected from the mixture liquid by filtration and dried. The target compound 3-formylphenylboronic acid was obtained in an amount of 123.46g. The yield thereof was 88percent. The results of the1H-NMR measurement of the resultant target compound (200 MHz, δ ppm, CDCl3) were as follows. 7.54 (t, J = 7.5 Hz, 1H), 7.93 (d, J = 6.1 Hz, 1H), 7.9 - 8.1 (br. d, 1H), 8.2 - 8.3 (br. s, 1H), 10.04 (s, 1H)Ferroacetylacetonate (0.025mmol), polymethylhydrogensiloxane0 75mmol), Potassium persulfate (0.25mmol), lah (0.25mmol), AcetonitrilelmL), waterlmL), in the reaction mixture 80 ° C reaction under 12 h. The reaction is finished adding ammonia water (2 ml) to remove the peripheric, add saturated salt water 10 ml, and extraction with ethyl ether (10 ml × 3), the combined organic phase, pressure reducing evaporate the solvent column chromatography to obtain yield 73percent.Under nitrogen, the above-obtained m-bromobenzeneboronic acid trimer was added to anhydrous tetrahydrofuran (600 ml)After the addition, transfer to a 2 L three-necked flask and add dimethylformamide (80.4 g, 1.1 mol). Then cool the system to -Below 70 ° C, 440 ml (1.1 moles) of 2.5 M n-butyllithium hexane solution was slowly added dropwise, and the temperatureThe maximum is not more than -60 ° C, and the addition is continued until the stirring is continued for 1 to 3 hours, followed by natural stirring to room temperature3-5 hours. TLC detection reaction is completed, the system cooled to 0 , adding 10percent hydrochloric acid aqueous solution quenching reaction, adjust the PH to1-2 continue at room temperature for 2-3 hours to ensure that the trimer hydrolysis is complete. The reaction solution was distilled, and the organic solvent was distilled and solidPrecipitation, filtration, toluene after recrystallization to be light yellow solid aldehyde phenyl benzene boric acid 106.5 grams, HPLC: 99.5percent, the total yield of two steps71percentUnder nitrogen protection, the above-obtained iodobenzeneboronic acid trimer was added to 500 ml of anhydrous tetrahydrofuranAfter the addition, the mixture was transferred to a 2 L three-necked flask and dimethylformamide (65.7 g, 0.90 mol) was added. The system was then cooled to -75 ° C to -80 ° C and a slow dropwise addition of 609 ml (0.98 mol) of 1.6 M n-butyllithium hexane solution was added dropwise. The addition temperature was not higher than -70 ° C during the addition and the temperature The reaction was continued for 1 to 3 hours, followed by spontaneously stirring at room temperature for 3-5 hours. TLC detection reaction is completed, the system cooled to 0 , adding 15percent hydrochloric acid aqueous solution quenching reaction, adjust the PH to 1-2 to room temperature stirring for 3-5 hours to ensure that the trimer hydrolysis complete. The reaction solution was distilled and the organic solvent was distilled, and the residue was precipitated by cooling. After recrystallization from acetonitrile, 86.6 g of aldehyde phenylbenzene borate was obtained as a pale yellow solid, and 99.8percent by HPLC and 77percent in two steps.

3-Formylphenylboronic acid can be used as reagent to study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye  and as exciton-coupled CD probes for epigallocatechin gallate Biological inhibitor of γ-glutamyltranspeptidase. suzuki reaction

Molecular Weight:149.94
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:150.0488242
Monoisotopic Mass:150.0488242
Topological Polar Surface Area:57.5
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes