ChemicalBook CAS DataBase List 3,5-DINITROBENZALDEHYDE

3,5-DINITROBENZALDEHYDE synthesis

7synthesis methods

Product Name:3,5-DINITROBENZALDEHYDE
CAS Number:14193-18-1
Molecular formula:C7H4N2O5
Molecular Weight:196.12

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Yield: 45.8 g (89%)

Reaction Conditions:

with hydrogenchloride;sodium hydrogencarbonate;triethylamine in tetrahydrofuran;dichloromethane;water;dimethyl sulfoxide

Steps:

83 (3,5-Dinitrobenzaldehyde)
EXAMPLE 83 (3,5-Dinitrobenzaldehyde) To a solution of oxalylchloride (26 ml, 0.30 mol) in CH₂Cl₂ (600 ml) DMSO (43 ml, 0.60 mol) was added, maintaining the temperature between -50° C. and -65° C. To the reaction solution was then added 3,5-dinitrobenzyl alcohol (50g), in THF (100 ml), maintaining the temperature between -50° C. and -65° C. The reaction mixture was stirred at -65° C. for 30 minutes and then triethylamine (170 ml) was added at -50° C. and -65° C. The reaction temperature was then adjusted to room temperature and H₂O (800 ml) was added. The organic phase was washed with sat. NaHCO₃ (500 ml), 5 times with diluted HCl (300 ml) and finally brine. The organic phase was then dried over MgSO₄ and the volatile solvents were removed at reduced pressure. The crude product was then triturated with heptane, which gave 45.8 g (89%) of 3,5-dinitrobenzaldehyde. ¹H NMR (CDCl₃, 300 MHz) δ ppm: 10.22 (s, 1H), 9.30 (d, 1H), 9.05 (t, 2H).

References:

Amersham Health AS US6448442, 2002, B1

71022-43-0
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14193-18-1
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References

99-33-2 Synthesis