ChemicalBook CAS DataBase List 3-Nitrobenzaldehyde

3-Nitrobenzaldehyde synthesis

14synthesis methods

Product Name:3-Nitrobenzaldehyde
CAS Number:99-61-6
Molecular formula:C7H5NO3
Molecular Weight:151.12

89 mL (1.7 mol) concentrated H2SO4 are filled in a 500 mL three-neck flask equipped with an internal thermometer and an addition funnel with pressure balance. Whilst cooling with an ice bath 45 mL (0.95 mol) fuming HNO3 are added carefully under stirring, the temperature must not exceed 10 °C. To this nitrating acid, 10.6 g (10.2 mL, 100 mmol) benzaldehyde are added under further cooling so that the temperature can be constantly kept at 15 °C (about 1 hour). The ice bath is removed and the reaction mixture is stored over night at room temperature.
The reaction mixture is poured in a 1 L beaker on 500 g crunched ice, the yellow precipitation is sucked off at 16 hPa over a Buechner funnel and washed with 200 mL of cold water. Crude yield (humid): 14.4 g
The humid crude product is dissolved in 125 mL tert-butyl methyl ether and then shaken out with 125 mL of a 5% NaHCO3 solution. The organic phase is dried over sodium sulfate, filtered and the solvent evaporated at a rotary evaporator. The residue is recrystallized from toluene / petroleumether (60-80 °C) by dissolving it in toluene whilst heating and then adding the double amount of petroleum ether in portions under ice cooling. The crystalllized light yellow 3-nitrobenzaldehyde is sucked off over a Buechner funnel. The product is dried over silica gel in an evacuated desiccator.
Yield: 8.0 g (53 mmol, 53%); mp 56 °C

99-08-1
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99-61-6
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Yield:99-61-6 98%

Reaction Conditions:

with laccase of Pleurotus ostreatus MTCC-1801;2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt in 1,4-dioxane at 20; pH=4.5;Enzymatic reaction;

Steps:

Bioconversions in the Presence of ABTS

General procedure: The biotransformation of toluene to benzaldehyde [32-34] was done in 15mLof 100mM sodium acetate buffer pH 4.5 containing 20mM toluene in dioxane,0.1mM ABTS, and 500 mL of twice-diluted crude laccase (activity of concentratedlaccase was 1.91 IU=mL) kept in a 100-mL conical flask, which was stirred vigorouslyfor 60 min (completion of the reaction was confirmed by the UV=vis spectrophotometer(Hitachi, Japan, model U-2900). The reaction solution was extractedthree times with 40mL of ethyl acetate, and 20 mL of the n-ethyl acetate extractwas injected in Waters HPLC model 600E using spherisorb C18 5 UV, 4.5250mmmm column. The mobile phase was methanol at the flow rate of 0.5mL=min. Thedetection was made using Waters UV detector model 2487 at k254 nm.

References:

Chaurasia, Pankaj Kumar;Yadava, Sudha;Bharati, Shashi Lata;Singh, Sunil Kumar [Synthetic Communications,2014,vol. 44,# 17,p. 2535 - 2544]