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| | 3,5-Dimethoxyphenylboronic acid Basic information |
| Product Name: | 3,5-Dimethoxyphenylboronic acid | | Synonyms: | 3,5-DimethoxyphenyL;3,5-Dimethoxyphenylboronic Acid (contains varying amounts of Anhydride);3,5-Dimethoxyphenylboronic acid, (contains various amounts of anhydride);3,5-Dimethoxyphenylboronic acid ,98%;3,5-Dimethoxyphenylboronic Acid, (Contains Various Amounts Of Anhydr;B-(3,5-dimethoxyphenyl)boronic acid;5-DiMethoxyphenylboronic acid;3,5-DIMETHOXYPHENYLBORONIC ACID | | CAS: | 192182-54-0 | | MF: | C8H11BO4 | | MW: | 181.98 | | EINECS: | | | Product Categories: | B (Classes of Boron Compounds);Boronic Acids;blocks;BoronicAcids;Heterocyclic Compounds;Boronic Acid | | Mol File: | 192182-54-0.mol |  |
| | 3,5-Dimethoxyphenylboronic acid Chemical Properties |
| Melting point | 202-207 °C | | Boiling point | 371.6±52.0 °C(Predicted) | | density | 1.19±0.1 g/cm3(Predicted) | | Fp | 81℃ | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in methanol. | | pka | 7.67±0.10(Predicted) | | form | powder to crystal | | color | White to Light yellow to Light orange | | InChI | 1S/C8H11BO4/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5,10-11H,1-2H3 | | InChIKey | XUIURRYWQBBCCK-UHFFFAOYSA-N | | SMILES | COc1cc(OC)cc(c1)B(O)O | | CAS DataBase Reference | 192182-54-0(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39 | | WGK Germany | 3 | | Hazard Note | Irritant/Keep Cold | | HazardClass | IRRITANT, KEEP COLD | | HS Code | 29163990 | | Storage Class | 11 - Combustible Solids |
| | 3,5-Dimethoxyphenylboronic acid Usage And Synthesis |
| Chemical Properties | Gray to white solid | | Uses | 3,5-Dimethoxyphenylboronic acid is a useful reagent for palladium-catalyst and Suzuki-Miyaura cross coupling reactions. | | Uses | Reactant for:
- Palladium-catalyzed coupling reactions
- Preparation of benzopyranone derivatives as positive GABAA receptor modulators
- Preparation of aryl alkenes via three-component coupling catalyzed by palladium
- Suzuki-Miyaura coupling
- Rhodium catalyzed cyanation with N-cyano-N-phenyl-p-methylbenzenesulfonamide
- Preparation of bisphosphonate inhibitors of human farnesyl pyrophosphate synthase
| | Uses | suzuki reaction | | Synthesis | 1. Synthesis of 3,5-dimethoxyphenylboronic acid: After cooling the flame-dried reaction vessel under argon protection, 3,5-dimethoxybromobenzene (3 g, 13.82 mmol) and anhydrous tetrahydrofuran (36 ml) were added. The mixture was stirred until a clarified solution was formed. Subsequently, the reaction mixture was cooled to -78 °C and maintained at this temperature for 15 minutes. n-Butyllithium (10.92 ml, 2.1 M hexane solution) was slowly added and the reaction mixture continued to be stirred at -78 °C for 30 minutes. Then, triisopropyl borate (5.2 g, 27.64 mmol) was added dropwise and the reaction was continuously stirred at -78°C for 2 hours. After completion of the reaction, it was slowly warmed up to room temperature and acidified with 2 M sulfuric acid solution to pH 2. The reaction mixture was extracted with ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by recrystallization from petroleum ether to give 3,5-dimethoxyphenylboronic acid in 92% yield. | | References | [1] Patent: WO2008/118802, 2008, A1. Location in patent: Page/Page column 25-26 |
| | 3,5-Dimethoxyphenylboronic acid Preparation Products And Raw materials |
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