Salicylaldehyde
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| Names | |||
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Preferred IUPAC name
2-Hydroxybenzaldehyde
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| Other names
Salicylaldehyde (no longer recommended)
Salicylic aldehyde o-Hydroxybenzaldehyde |
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| Identifiers | |||
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3D model (Jmol)
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.001.783 | ||
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| Properties | |||
| 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) | ||
| -64.4·10−6 cm3/mol | |||
| Related compounds | |||
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Related compounds
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Salicylic acid Benzaldehyde Salicylaldoxime |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| 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.
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