| Identification | More | [Name]
3,5-Dimethoxyphenylboronic acid | [CAS]
192182-54-0 | [Synonyms]
3,5-DIMETHOXYBENZENEBORONIC ACID
3,5-DIMETHOXYPHENYLBORONIC ACID
AKOS BRN-0893
3,5-DIMETHOXYPHENYLBORONIC ACID 99%
3,5-Dimethoxyphenylboronic Acid (contains varying amounts of Anhydride)
3,5-Dimethoxyphenylboronic acid, (contains various amounts of anhydride)
3,5-Dimethoxyphenylboronic acid ,98% | [Molecular Formula]
C8H11BO4 | [MDL Number]
MFCD03095127 | [Molecular Weight]
181.98 | [MOL File]
192182-54-0.mol |
| Chemical Properties | Back Directory | [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 Cold | [solubility ]
Soluble in methanol. | [form ]
powder to crystal | [pka]
7.67±0.10(Predicted) | [color ]
White to Light yellow to Light orange | [Detection Methods]
HPLC,NMR | [CAS DataBase Reference]
192182-54-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Gray to white solid | [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]
3,5-Dimethoxyphenylboronic acid is a useful reagent for palladium-catalyst and Suzuki-Miyaura cross coupling reactions. | [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 |
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