4-Bromo-2,5-dimethoxybenzaldehyde
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4-Bromo-2,5-dimethoxybenzaldehyde
structure -
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CAS No:
31558-41-5
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Formula:
C9H9BrO3
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Chemical Name:
4-Bromo-2,5-dimethoxybenzaldehyde
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Synonyms:
4-bromo-2,5-dimethoxybenzaldehyde;2,5-dimethoxy-4-bromobenzaldehyde;MFCD00156964;370884-62-1;PubChem2068;Benzaldehyde, 4-bromo-2,5-dimethoxy-;ACMC-1AIQ9;CBMicro_047429;Cambridge id 6238031;MixCom6_002373
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CAS No:
Characteristics
35.5
2
1.5±0.1 g/cm3
132-135°C
337.1°C at 760 mmHg
157.7±27.9 °C
1.568
Insoluble in water.
Safety Information
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 6 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Bromo-2,5-dimethoxybenzaldehyde Use and Manufacturing
To a solution of 2, 5-dimethoxybenzaldehyde (1.0 g, 6.02 mmol) in glacial acetic acid (7 mL) was added a solution of Br2 (0.34 mL, 6.62 mmol) in glacial acetic acid (3 mL) at 0 °C and the reaction mixture was warmed up and stirred at room temperature for 1 h. Water (30 mL) was added and the precipitate was collected by filtration. Water (30 mL) and CH2Cl2 (30 mL) were added to the white solid and the two phases were separated. The aqueous layer was extracted with CH2Cl2 (3 x 25 mL) and the combined organic layers were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product which was further purified by column chromatography on silica (20percent EtOAc/hexanes) to furnish 4-bromo-2, 5-dimethoxybenzaldehyde as a pale yellow solid (0.83 g, 3.37 mmol, 56 percent).SnCl2, 5-Dimethoxybromobenzene (5) (7.0 ml :47 mmol) was dissolved in 160 ml of dichloromethane. The solution was added with 13 ml (0.12 mol) of titanium chloride (IV) under argon atmosphere at -78°C, subsequently with 8.2 ml (0.14 mol ) of dichloromethylmethy ether, and stirred at -78°C for one hour. The reaction mixture was gradually added to 600 ml of ice water and extracted with dichloromethane. The dichloromethane layer was washed with an aqueous saturated sodium hydrogencarbonate solution, water, and saturated brine, and then dried over sodium sulfate. The dichloromethane was evaporated under reduced pressure, and the residue was purified by silica gel column to obtain 9.9 g of Compound (6) (yield 87 percent).1H-NMR (CDCl3, 300 MHz): 10.40 (s, 1H), 7.34 (s, 1H), 7.25 (s, 1H), 3.91 (s, 3H), 3.90 (s, 3H)Under a N2 atmosphere in 500 mL of benzene was combined 11.4 g (0.0465 mol) of
Computed Properties
Molecular Weight:245.07
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:243.97351
Monoisotopic Mass:243.97351
Topological Polar Surface Area:35.5
Heavy Atom Count:13
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-Bromo-2,5-dimethoxybenzaldehyde
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