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| | 2,6-Dimethoxyphenylboronic acid Basic information |
| | 2,6-Dimethoxyphenylboronic acid Chemical Properties |
| Melting point | 110-112 °C (lit.) | | Boiling point | 372.8±52.0 °C(Predicted) | | density | 1.19±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Powder | | pka | 8.58±0.58(Predicted) | | color | White to beige | | BRN | 3032352 | | InChI | InChI=1S/C8H11BO4/c1-12-6-4-3-5-7(13-2)8(6)9(10)11/h3-5,10-11H,1-2H3 | | InChIKey | BKWVXPCYDRURMK-UHFFFAOYSA-N | | SMILES | B(C1=C(OC)C=CC=C1OC)(O)O | | CAS DataBase Reference | 23112-96-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26-36/37 | | WGK Germany | 3 | | Hazard Note | Irritant/Keep Cold | | HazardClass | IRRITANT | | HS Code | 29319090 | | Storage Class | 11 - Combustible Solids |
| | 2,6-Dimethoxyphenylboronic acid Usage And Synthesis |
| Chemical Properties | white to beige powder | | Uses | 2,6-Dimethoxyphenylboronic acid can be used as a reagent in:
The palladium-catalyzed Suzuki-Miyaura coupling reaction to construct carbon-carbon bond.
The synthesis of 2H-imidazo[1,5-a]pyridin-4-ium bromides, which are utilized as precursors for the preparation of N-heterocyclic carbene ligands.
The preparation of monosubstituted benzothiazoloquinazolinones as potential monoamine oxidases inhibitors.
Reactant for:
Suzuki-Miyaura reactions | | Synthesis | The general procedure for the synthesis of 2,6-dimethoxyphenylboronic acid from trimethyl borate and m-phenylene dimethyl ether was as follows: 41.5 g (0.3 mol) of 1,3-dimethoxybenzene and 170 g of THF were added to a dry 1L three-neck flask. The reaction system was cooled to -30~-40°C under nitrogen protection and stirred. 240 ml (0.6 mol) of n-butyllithium in hexane solution was added slowly dropwise. After the dropwise addition, the reaction system was slowly warmed to 10~30°C and maintained at this temperature for 1 hour. Subsequently, the system was again cooled to -30~-40 °C and 62.4 g (0.6 mol) of trimethyl borate was slowly added dropwise. After the dropwise addition was completed, the reaction was maintained at this temperature for 1 hour. After the reaction was completed, 148 g of concentrated hydrochloric acid and 150 g of water were added to the system and stirred at 20-30 °C for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure until no solvent evaporated. The residue was dissolved in 200 g of water and stirred for 20 min, followed by filtration using a Brinell funnel to give 45 g of white solid product in 90.0% yield. The product was analyzed by gas chromatography and the purity was 99.0%. | | References | [1] Patent: WO2004/24738, 2004, A1. Location in patent: Page/Page column 13-14
[2] Patent: CN105348240, 2016, A. Location in patent: Paragraph 0059; 0060
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4664 - 4668
[4] Organic Letters, 2012, vol. 14, # 16, p. 4250 - 4253
[5] Patent: KR2016/90242, 2016, A. Location in patent: Paragraph 0162; 0163; 0164; 0165; 0166; 0167; 0168 |
| | 2,6-Dimethoxyphenylboronic acid Preparation Products And Raw materials |
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