Structure via PubChem · Public domain (PubChem)
salicylaldehyde
Sign in to saveAlso known as o-formylphenol, salicylal, 2-Formylphenol, Salicylic aldehyde, Salicylaldehyde, 8CI, FEMA 3004, 2-hydroxybenzaldehyde
Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula . 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 precursor to coumarin and a variety of chelating agents.
Chemical data
- Formula
- C7H6O2
- Molecular weight
- 122.12 g/mol
- IUPAC name
- 2-hydroxybenzaldehyde
- SMILES
- C1=CC=C(C(=C1)C=O)O
- InChIKey
- SMQUZDBALVYZAC-UHFFFAOYSA-N
- XLogP
- 1.8
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
~3 min read
Encyclopedic overview
5 sectionsContents
- Production
- Natural occurrences
- Reactions and applications
- Internal hydrogen bonding
- References
Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula . 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 precursor to coumarin and a variety of chelating agents.
== Production == Salicylaldehyde is produced by condensation of phenol with formaldehyde to give hydroxybenzyl alcohol, which is oxidized to the aldehyde. Salicylaldehydes in general are prepared by ortho-selective formylation reactions from the corresponding phenol, for instance by the Duff reaction, Reimer–Tiemann reaction, or by treatment with paraformaldehyde in the presence of magnesium chloride and a base. 300px|Preparation of salicylaldehyde by the Reimer–Tiemann reaction
Excerpted from Wikipedia’s “salicylaldehyde” article, available under the CC BY-SA 4.0 licence.