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84160

Sigma-Aldrich

Salicylaldehyde

redist., ≥99.0% (GC)

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Synonym(s):
2-Hydroxybenzaldehyde
Linear Formula:
2-(HO)C6H4CHO
CAS Number:
90-02-8
Molecular Weight:
122.12
Beilstein:
471388
MDL number:
MFCD00003317
UNSPSC Code:
12352100
PubChem Substance ID:
57652989
NACRES:
NA.22

vapor density

4.2 (vs air)

Quality Level

100

vapor pressure

1 mmHg ( 33 °C)

Assay

≥99.0% (GC)

form

liquid

quality

redist.

impurities

≤0.2% water

refractive index

n20/D 1.573 (lit.)
n20/D 1.573

bp

197 °C (lit.)

mp

1-2 °C (lit.)

density

1.146 g/mL at 25 °C (lit.)

SMILES string

Oc1ccccc1C=O

InChI

1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H

InChI key

SMQUZDBALVYZAC-UHFFFAOYSA-N

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Application

Salicylaldehyde can be used to synthesize:
  • Salicylidene-tris(aminomethyl)ethane chelating agent which can form metal chelates with Fe3+, probes for 19F magnetic resonance imaging.
  • Schiff base ligands via condensation with cycloalkylamines.
  • 3-acetylcoumarin, an intermediate for the synthesis of various pyrrolidone fused coumarins and furan fused coumarins.
  • Biologically important 2-amino-4H-chromene scaffolds via multicomponent reaction with nitroalkanes and malononitrile.

Signal Word

Warning

Hazard Statements

H302,H315,H319,H341,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Muta. 2 - Skin Irrit. 2

WGK

WGK 2

Flash Point(F)

170.6 °F

Flash Point(C)

77 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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A detailed investigation of the multicomponent reaction of salicylaldehyde, ethyl acetoacetate and isocyanides under microwave heating.
Amanpour T, et al.
Tetrahedron, 71(39), 7159-7169 (2015)
Fluorous-Soluble Metal Chelate for Sensitive Fluorine-19 Magnetic Resonance Imaging Nanoemulsion Probes.
Jahromi AH, et al.
ACS Nano (2018)
Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes.
Elinson MN, et al.
Tetrahedron, 66(23), 4043-4048 (2010)
Organometallic-mediated radical polymerization using well-defined Schiff base cobalt (II) complexes.
Silva YF, et al.
Journal of Coordination Chemistry, 1-22 (2018)
Stephen K Murphy et al.
Organic letters, 13(23), 6216-6219 (2011-11-09)
A method has been developed for the intermolecular hydroacylation of homoallyl alcohols with salicylaldehydes to furnish homoaldol products in 50-98% yields. The method also applies to the hydroacylation of 2-hydroxystyrenes. This work highlights the use of hydroacylation as a unified
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