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.
In the Vinony graph
Vinony's link graph records 53 inbound references to salicylaldehyde, and connects out to chelation, International Standard Book Number and mass density.
It is catalogued under topics including 2-Hydroxyphenyl compounds, Chembox having GHS data and ECHA InfoCard ID from Wikidata.
Vinony links it to 27 Wikipedia language editions.
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
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 122.037
Show 17 more facts
- found in taxon
- Festuca rubra
- chemical formula
- C₇H₆O₂
- canonical SMILES
- C1=CC=C(C(=C1)C=O)O
- electric dipole moment
- 2.86
- refractive index
- 1.5740
- flash point
- 78
- melting point
- -7
- density
- 1.1674
- Commons category
- Salicylaldehyde
- boiling point
- 197
- pKa
- 8.37
- vapor pressure
- 0.075
- solubility
- 8.37
- partition coefficient water/octanol
- 1.81
- median lethal dose (LD50)
- 3
- safety classification and labelling
- Regulation (EC) No. 1272/2008
- fabrication method
- Reimer–Tiemann reaction
via Wikidata · CC0
~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.