2-Aminobenzaldehyde

2-Aminobenzaldehyde

Names
Other names ortho-Aminobenzaldehyde, Formylaniline
Identifiers
CAS Number	529-23-7
3D model (JSmol)	Interactive image
ChemSpider	61553
EC Number	208-454-3
PubChem CID	68255
InChI InChI=1S/C7H7NO/c8-7-4-2-1-3-6(7)5-9/h1-5H,8H2 Key: FXWFZIRWWNPPOV-UHFFFAOYSA-N
SMILES C1=CC=C(C(=C1)C=O)N
Properties
Chemical formula	C7H7NO
Molar mass	121.14 g·mol−1
Appearance	yellow solid
Melting point	32–34 °C (90–93 °F; 305–307 K)
Solubility in water	good
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

Preparation and reactions

It is usually prepared by reduction of 2-nitrobenzaldehyde with iron^[1] or iron(II) sulfate.^[2] The compound is unstable with respect to condensation with itself.

It 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.

Structure of nickel-aquo nitrate complex of the ligand derived from trimerization of 2-aminobenzaldehyde.^[3]

References

1. ↑ 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. 
2. ↑ Lee Irvin Smith; J. W. Opie (1948). "o-Aminobenzaldehyde". Org. Synth. 28: 11. doi:10.15227/orgsyn.028.0011. 
3. ↑ 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: 637–642. doi:10.1021/ic50027a008. CS1 maint: Multiple names: authors list (link)