ChemicalBook--->CAS DataBase List--->476620-54-9

476620-54-9

476620-54-9 Structure

476620-54-9 Structure
IdentificationBack Directory
[Name]

2-Bromo-4,5-difluorobenzaldehyde
[CAS]

476620-54-9
[Synonyms]

5-difluorobenzaldehyde
2-Bromo-4,5-difluorobenzaldehyde
Benzaldehyde, 2-bromo-4,5-difluoro-
2-Bromo-4,5-difluorobenzaldehyde,98%
2-Bromo-4,5-difluorobenzaldehyde ISO 9001:2015 REACH
[Molecular Formula]

C7H3BrF2O
[MDL Number]

MFCD16659662
[MOL File]

476620-54-9.mol
[Molecular Weight]

220.999
Chemical PropertiesBack Directory
[Boiling point ]

232.0±35.0 °C(Predicted)
[density ]

1.758±0.06 g/cm3(Predicted)
[storage temp. ]

Room temperature.
[form ]

Powder
[color ]

Off-white
[Water Solubility ]

Slightly soluble in water.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[HS Code ]

2913000090
Hazard InformationBack Directory
[Uses]

It is an important intermediate for pharmaceutical and organic synthesis.
[Synthesis]

(2-Bromo-4,5-difluorophenyl)methanol

476620-55-0

2-Bromo-4,5-difluorobenzaldehyde

476620-54-9

General procedure for the synthesis of 2-bromo-4,5-difluorobenzaldehyde from (2-bromo-4,5-difluorophenyl)methanol: (2-bromo-4,5-difluorophenyl)methanol (1.23 g, 5.50 mmol), triethylamine (1.39 g, 13.75 mmol) and dimethylsulfoxide (1.72 g, 22.00 mmol) were dissolved in dichloromethane (25 mL) in dichloromethane (25 mL) and cooled to 0°C. Subsequently, sulfur trioxide-pyridine complex (1.32 g, 8.25 mmol) was added in batches. The reaction mixture was stirred at 0 °C for 1 h. Triethylamine (1.39 g, 13.75 mmol), dimethyl sulfoxide (1.72 g, 22.00 mmol) and sulfur trioxide-pyridine complex (1.32 g, 8.25 mmol) were added again. After continued stirring at 0 °C for 30 min, the reaction solution was diluted with dichloromethane (50 mL) and washed sequentially with saturated sodium bicarbonate solution and saturated sodium thiosulfate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by fast column chromatography (RediSep fast column, 230-400 mesh silica gel, eluent 10-30% ethyl acetate in hexane solution) afforded 2-bromo-4,5-difluorobenzaldehyde (0.47 g, 39% yield).1H NMR (300 MHz, CDCl3) δ 10.23 (s, 1H), 7.77 (m, 1H), 7.52 (m, 1H).

[References]

[1] Patent: WO2010/55005, 2010, A1. Location in patent: Page/Page column 70-71
[2] Patent: WO2011/20193, 2011, A1. Location in patent: Page/Page column 18-19
[3] Patent: WO2011/57382, 2011, A1. Location in patent: Page/Page column 21
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1953 - 1957
Spectrum DetailBack Directory
[Spectrum Detail]

2-Bromo-4,5-difluorobenzaldehyde(476620-54-9)1HNMR
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