2-hydroxybenzaldehyde

Salicylaldehyde

Names
Preferred IUPAC name 2-Hydroxybenzaldehyde
Other names Salicylaldehyde (no longer recommended) Salicylic aldehyde o-Hydroxybenzaldehyde
Identifiers
CAS Number	90-02-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16008 Y
ChemSpider	13863618 Y
ECHA InfoCard	100.001.783
UNII	17K64GZH20 Y
InChI InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H Y Key: SMQUZDBALVYZAC-UHFFFAOYSA-N Y InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H Key: SMQUZDBALVYZAC-UHFFFAOYAD
SMILES O=Cc1ccccc1O
Properties
Chemical formula	C7H6O2
Molar mass	122.12 g/mol
Density	1.146 g/cm3
Melting point	−7 °C (19 °F; 266 K)
Boiling point	196 to 197 °C (385 to 387 °F; 469 to 470 K)
Magnetic susceptibility (χ)	-64.4·10−6 cm3/mol
Related compounds
Related compounds	Salicylic acid Benzaldehyde Salicylaldoxime
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Salicylaldehyde (2-hydroxybenzaldehyde) is the organic compound with the formula C₆H₄CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a key precursor to a variety chelating agents, some of which are commercially important.

Salicylaldehyde is prepared from phenol and chloroform by heating with sodium hydroxide or potassium hydroxide in a Reimer–Tiemann reaction:

Alternatively, it is produced by condensation of phenol or its derivatives with formaldehyde to give hydroxybenzyl alcohol, which is oxidized to the aldehyde.

Salicylaldehydes in general may be prepared from the corresponding phenol by the Duff reaction, or by treatment with paraformaldehyde in the presence of magnesium chloride and a base.

Salicylaldehyde was identified as a characteristic aroma component of buckwheat.

It is also one of the components of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the European beaver (Castor fiber), used in perfumery.

Furthermore, salicylaldehyde occurs in the larval defensive secretions of several leaf beetle species that belong the subtribe Chrysomelina. An example for a leaf beetle species that produces salicylaldehyde is the red poplar leaf beetle Chrysomela populi.