2-Aminobenzaldehyde

2-Aminobenzaldehyde
Names
Preferred IUPAC name
2-Aminobenzaldehyde
Other names
ortho-Aminobenzaldehyde
2-Formylaniline
2-Aminobenzenecarbaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.687 Edit this at Wikidata
EC Number
  • 208-454-3
UNII
  • InChI=1S/C7H7NO/c8-7-4-2-1-3-6(7)5-9/h1-5H,8H2
    Key: FXWFZIRWWNPPOV-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)C=O)N
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).

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]

Preparation and reactions

It 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:

The Friedländer synthesis
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 condensation of three equivalents of 2-aminobenzaldehyde.[4]

References

  1. ^ Thummel, Randolph P. (2001). "2-Aminobenzaldehyde". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ra088. ISBN 0471936235.
  2. ^ 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.
  3. ^ Lee Irvin Smith; J. W. Opie (1948). "o-Aminobenzaldehyde". Org. Synth. 28: 11. doi:10.15227/orgsyn.028.0011.
  4. ^ 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.