2-Aminobenzaldehyde is an organic compound with the formula C6H4(NH2)CHO. It is one of three isomers of aminobenzaldehyde. It is a low-melting yellow solid that is soluble in water.[1]
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| Names | |
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| Preferred IUPAC name
2-Aminobenzaldehyde | |
| Other names
ortho-Aminobenzaldehyde
2-Formylaniline 2-Aminobenzenecarbaldehyde | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.687 |
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CompTox Dashboard (EPA)
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| Properties | |
| C7H7NO | |
| Molar mass | 121.139 g·mol−1 |
| Appearance | yellow solid |
| Melting point | 32–34 °C (90–93 °F; 305–307 K) |
| good | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and reactions
editIt is usually prepared by reduction of 2-nitrobenzaldehyde with iron[2] or iron(II) sulfate.[3] Like related aminoaldehydes, it is unstable with respect to self-condensation.
2-Aminobenzaldehyde is used to prepare quinolines by the Friedländer synthesis:
By template reactions, it also forms trimeric and tetrameric condensation products that have been studied as ligands.
References
edit- ^ Thummel, Randolph P. (2001). "2-Aminobenzaldehyde". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ra088. ISBN 0471936235.
- ^ Chen Zhang; Chandra Kanta De; Daniel Seidel (2012). "o-Aminobenzaldehyde, Redox-Neutral Aminal Formation and Synthesis of Deoxyvasicinone". Org. Synth. 89: 274. doi:10.15227/orgsyn.089.0274.
- ^ Lee Irvin Smith; J. W. Opie (1948). "o-Aminobenzaldehyde". Org. Synth. 28: 11. doi:10.15227/orgsyn.028.0011.
- ^ Fleischer, E. B.; Klem, E. (1965). "The Structure of a Self-Condensation Product of o-Aminobenzaldehyde in the Presence of Nickel Ions". Inorganic Chemistry. 4 (5): 637–642. doi:10.1021/ic50027a008.