| Identification | More | [Name]
2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde | [CAS]
6451-86-1 | [Synonyms]
2-BROMO-4-METHOXY-5-(BENZYLOXY)BENZALDEHYDE
5-BENZYLOXY-2-BROMO-4-METHOXY-BENZALDEHYDE
6-BROMOBENZYL ISOVANILLIN
5-Benzyl-2-bromo-4-methoxylbenzaldehyde | [Molecular Formula]
C15H13BrO3 | [MDL Number]
MFCD00666893 | [Molecular Weight]
321.17 | [MOL File]
6451-86-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
142.4-143.3 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6)) | [Boiling point ]
427.5±40.0 °C(Predicted) | [density ]
1.421±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [Appearance]
White to off-white Solid | [CAS DataBase Reference]
6451-86-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
6-Bromobenzylisovanillin is an intermediate in the synthesis of 3,8-Dihydroxy-9-methoxy-6H-Dibenzo[b,d]pyran-6-one (D455545) which has been used in anti-wrinkle agents and is known as a collagen production promoter, MMP-1 production inhibitor and elastase activity inhibitor containing urolithin. | [Synthesis]
Under nitrogen protection, 2-bromo-5-hydroxy-4-methoxybenzaldehyde (8.70 mmol) was dissolved in 87 mL (0.1 M) of N,N-dimethylformamide (DMF) and cooled to 0 °C. Potassium carbonate (13.1 mmol, 1.8 g) and benzyl bromide (10.4 mmol, 1.77 g) were then added sequentially. The reaction mixture was slowly warmed to 25 °C and the reaction was stirred at this temperature for 5 hours. Upon completion of the reaction, the mixture was poured into 100 mL of aqueous ammonium chloride solution to quench the reaction. The reaction mixture was extracted with ethyl acetate (3 x 30 mL) and the organic layers were combined. The organic layer was washed with saturated saline (10 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 2-bromo-4-methoxy-5-benzyloxybenzaldehyde (5-(benzyloxy)-2-bromo-4-methoxybenzaldehyde) 2.73 g (8.53 mmol, 98% yield). | [References]
[1] Patent: KR101492960, 2015, B1. Location in patent: Paragraph 0092-0094
[2] Tetrahedron, 2006, vol. 62, # 51, p. 12098 - 12107
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 8, p. 1289 - 1292
[4] Patent: US2006/257337, 2006, A1. Location in patent: Page/Page column 16-17
[5] Patent: WO2016/29214, 2016, A1. Location in patent: Page/Page column 145 |
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