Salicylaldehyde | |
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2-Hydroxybenzaldehyde |
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Other names
Salicylic aldehyde; 2-Hydroxybenzaldehyde; o-Hydroxybenzaldehyde |
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Identifiers | |
CAS number | 90-02-8 |
ChemSpider | 13863618 |
UNII | 17K64GZH20 |
ChEBI | CHEBI:16008 |
ChEMBL | CHEMBL108925 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C7H6O2 |
Molar mass | 122.12 g/mol |
Density | 1.146 g/cm3 |
Melting point |
-7 °C, 266 K, 19 °F |
Boiling point |
196–197 °C |
Related compounds | |
Related compounds | Salicylic acid Benzaldehyde Salicylaldoxime |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Salicylaldehyde (2-hydroxybenzaldehyde) is the chemical compound with the formula C6H4CHO-2-OH.[1] 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 and a characteristic buckwheat aroma at lower concentration. Salicylaldehyde was identified as a characteristic aroma component of buckwheat.[2] Salicylaldehyde is a key precursor to a variety chelating agents, some of which are commercially important. It can be prepared from phenol and chloroform by heating with sodium hydroxide or potassium hydroxide in a Reimer-Tiemann reaction:
Salicylaldehyde is a common highly-functionalized arene that has often been exploited as a precursor to still other chemicals, which are shown in the figure, from the left: catechol, benzofuran, a salicylaldehydimine (R = alkyl or aryl), 3-carbethoxycoumarin.
Salicylaldehyde undergoes a variety of chemical reactions including: