2-Aminobenzaldehyde

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]

2-Aminobenzaldehyde

Names
Preferred IUPAC name 2-Aminobenzaldehyde
Other names ortho-Aminobenzaldehyde 2-Formylaniline 2-Aminobenzenecarbaldehyde
Identifiers
CAS Number	529-23-7 Y
3D model (JSmol)	Interactive image
ChemSpider	61553
ECHA InfoCard	100.007.687
EC Number	208-454-3
PubChem CID	68255
UNII	EG769PG2AX Y
CompTox Dashboard (EPA)	DTXSID6060183
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	121.139 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

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

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]