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4-Nitrobenzaldehyde is an organic compound with the formula O 2 NC 6 H 4 CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group para-substituted to an aldehyde. 4-Nitrobenzaldehyde is obtained by oxidation of 4-nitrotoluene or hydrolysis of 4-nitrobenzalbromide: [3] O 2 NC 6 H 4 CHBr 2 + H 2 O → O 2 NC 6 H 4 CHO + 2 HBr
Nitrobenzaldehyde may refer to any of the three isomeric chemical compounds : 2-Nitrobenzaldehyde; 3-Nitrobenzaldehyde; 4-Nitrobenzaldehyde; isomers of ...
4-Nitrobenzaldehyde This page was last edited on 26 August 2022, at 19:59 (UTC). Text is available under the Creative Commons Attribution-ShareAlike 4.0 License ...
3-Nitrobenzaldehyde is an organic compound with the formula O 2 NC 6 H 4 CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group meta-substituted to the aldehyde. 3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid. [3] C 6 H 5 CHO + HNO 3 → O 2 NC 6 H 4 CHO + H 2 O
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2-Nitrobenzaldehyde is an intermediate in an early route to indigo, a water-insoluble dye commonly used to dye jeans and other fabrics.In the Baeyer-Drewson indigo synthesis, 2-nitrobenzaldehyde condenses with acetone in basic aqueous solution to yield indigo in a one-pot synthesis [9] [10] The method was abandoned in the early part of the 20th century, being replaced by routes from aniline.
This approach relies on acyl transfer in the Mumm rearrangement to form the four-membered ring. The reaction proceeds in moderate yield at room temperature in methanol with formaldehyde or a variety of aryl aldehydes. For example, p-nitrobenzaldehyde reacts to form the β-lactam shown in 71% yield as a 4:1 diastereomeric mixture:
In the first step of the reaction mechanism the precursor molecule 2-nitrobenzaldehyde 4 is protonated, often by sulfuric acid, to intermediate 5, followed by an electrophilic attack to benzene (other arenes can be used as well). The resulting benzhydrol 6 cyclisizes to 7 and finally to compound 8.
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