2-Aminobenzaldehyde

2-Aminobenzaldehyde
Names
	Preferred IUPAC name 2-Aminobenzaldehyde
	Systematic IUPAC name 2-Aminobenzenecarbaldehyde
	Other names ortho-Aminobenzaldehyde; 2-Formylaniline
Identifiers
CAS Number	529-23-7;
3D model (JSmol)	Interactive image;
ChemSpider	61553;
ECHA InfoCard	100.007.687
EC Number	208-454-3;
PubChem CID	68255;
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

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] 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.[3]

References

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: 637–642. doi:10.1021/ic50027a008.

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[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.