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YELLOW CRYSTALLINE POWDER OR NEEDLES

2-Nitrobenzaldehyde is a benzaldhyde with a nitro group substituted in the ortho position. 2-Nitrobenzaldehyde is used in the preparation of dyes and colorants such as Indigo carmine. 2-Nitrobenzaldeh yde gas been shown to be a useful photoremovable protecting group as well as in the preparation of more effective ones such as o-Nitrophenylethylene glycol.

2-Nitrobenzaldehyde can react with chitosan to form 2-nitrobenzyl-chitosan, which is soluble in trifluoroacetic acid and can also be electrospun into nanofiber matrices. On photolysis, the nitrobenzyl group is cleaved to form neat chitosan nanofiber matrices. The same principle has been applied for the preparation of gelatin nanofiber matrices. The condensation of o-NBA with 2-aminobenzothiazole forms o-nitrobenzylidene 2-aminobenzothiazole, a Schiff′s base that can react with metal ions to form complexes.

ChEBI: Benzaldehyde substituted at the ortho-position with a nitro group.

2-Nitrobenzaldehyde is synthesized from 2-Nitrotoluene by nitration and oxidation.
Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene

Synthetic Communications, 19, p. 3385, 1989 DOI: 10.1080/00397918908052745

Crystallise the aldehyde from toluene (2-2.5mL/g) by addition of 7mL pet ether (b 40-60o) for 1mL of solution. It can also be distilled under reduced pressures. [Beilstein 7 IV 584.]