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| | 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester Basic information | | Uses |
| Product Name: | 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester | | Synonyms: | 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester;1,3-Benzenedicarboxylic acid, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,3-dimethyl ester;DiMethyl 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)isophthalate;3,5-Bis(Methoxycarbonyl)benzeneboronic acid pinacol ester, 97%;benzene-1,3,5-tris(3',5'-benzenedicarboxylic acid diMethyl ester);dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxylate;dimethyl 5-(pinacolboryl)isophthalate;3,5-Bis(methoxycarbonyl)benzeneboronicacidpinacolester,97% | | CAS: | 944392-68-1 | | MF: | C16H21BO6 | | MW: | 320.15 | | EINECS: | | | Product Categories: | Organic boronic acid | | Mol File: | 944392-68-1.mol |  |
| | 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester Chemical Properties |
| Melting point | 128℃ | | Boiling point | 435.4±35.0 °C(Predicted) | | density | 1.16±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Solid | | color | Pale pink | | InChI | InChI=1S/C16H21BO6/c1-15(2)16(3,4)23-17(22-15)12-8-10(13(18)20-5)7-11(9-12)14(19)21-6/h7-9H,1-6H3 | | InChIKey | IGSNWXAGFXHYOG-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)=CC(B2OC(C)(C)C(C)(C)O2)=CC(C(OC)=O)=C1 |
| | 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester Usage And Synthesis |
| Uses | 3,5-bis(methoxycarbonyl)phenylboronic acid pinacol ester is an organic intermediate that can be used in the Suzuki coupling reaction. It can be used to prepare rigid aromatic tricarboxylic acid ligands such as 5-[4-(1-carboxynaphthyl)]-isophthalic acid. Rigid aromatic tricarboxylic acid ligands are widely used in the construction of MOF materials. These materials typically possess excellent pore structures and large specific surface areas, making them potential applications in various fields such as energy gas storage and separation, catalysis, chemical sensing, and drug delivery. | | Synthesis | General procedure for the synthesis of 3,5-dimethoxycarbonylphenylboronic acid pinacol ester from dimethyl 5-bromoisophthalate and pinacol ester of bisboronic acid: dimethyl 5-bromo-1,3-benzenedicarboxylate (5.4 g, 19.8 mmol) and pinacol ester of boronic acid (6.0 g, 29.4 mmol) were added into a 250 mL three-necked flask and anhydrous 1,4-dioxane (50 mL) was added As a solvent, Pd(dppf)2Cl2 (0.2 g, 0.27 mmol) was added under nitrogen protection. The reaction mixture was heated to 100 °C and kept for 12 hours. Upon completion of the reaction, it was cooled to room temperature and the excess 1,4-dioxane was removed by distillation. Water (20 mL) was added and extracted with ethyl acetate (30 mL x 3), the organic phases were combined and dried with anhydrous Na2SO4. After filtration, the filtrate was evaporated to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=94/6) to afford 3,5-dimethoxycarbonylphenylboronic acid pinacol ester (4.59 g, 72% yield) in white powder form. | | References | [1] Chemical Communications, 2015, vol. 51, # 40, p. 8508 - 8511
[2] Journal of the American Chemical Society, 2013, vol. 135, # 32, p. 11887 - 11894
[3] Patent: CN105237337, 2016, A. Location in patent: Paragraph 0021
[4] Chemical Communications, 2013, vol. 49, # 20, p. 2043 - 2045
[5] Inorganic Chemistry, 2015, vol. 54, # 9, p. 4377 - 4381 |
| | 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester Preparation Products And Raw materials |
| Raw materials | DIMETHYL 5-BROMOISOPHTHALATE-->Dimethyl 5-aminoisophthalate-->DIMETHYL 5-CHLOROISOPHTHALATE-->DIMETHYL 5-IODOISOPHTHALATE-->5-BROMOISOPHTHALIC ACID-->Isophthalic acid-->5-Aminoisophthalic acid-->Dimethyl isophthalate-->Pinacolborane-->Bis(pinacolato)diboron | | Preparation Products | Diphenylethyne- 3, 3', 5, 5'-tetracarboxylic acid (PCN-14)-->Biphenyl-3,4′,5-tricarboxylic acid-->3,5-Bis(methoxycarbonyl)phenylboronic acid-->[1,1':3',1''-Terphenyl]-3,3'',5,5''-tetracarboxylic acid, 5'-methyl- |
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