S356

Sigma-Aldrich

Salicylaldehyde

reagent grade, 98%

Synonym(s):
2-Hydroxybenzaldehyde
Linear Formula:
2-(HO)C6H4CHO
CAS Number:
Molecular Weight:
122.12
Beilstein/REAXYS Number:
471388
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

reagent grade

vapor density

4.2 (vs air)

vapor pressure

1 mmHg ( 33 °C)

assay

98%

impurities

≤1% phenol

refractive index

n20/D 1.573 (lit.)

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 may be used as starting reagent in the synthesis of novel unsymmetrical chiral Salen Schiff base ligands. It may be used in the preparation of salicylaldehyde phenylhydrazine, a useful indicator for the titration of organometallic reagents.
Salicyladehyde (2-Hydroxybenzaldehyde) may be used in the preparation of pyrocatechol via Dakin reaction.

Packaging

100, 500 g in glass bottle
1 kg in glass bottle

Signal Word

Warning

hazcat

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

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Salicin from host plant as precursor of salicylaldehyde in defensive secretion of chrysomeline larvae.
Pasteels JM, et al.
Physiological Entomology, 8(3), 307-314 (1983)
Unsymmetric chiral salen Schiff bases: A new chiral ligand pool from bis-schiff bases containing two different salicylaldehyde units.
Lopez J, et al.
Tetrahedron Letters, 39(24), 4199-4202 (1998)
Eagleson M.
Concise Encyclopedia Chemistry, 301-301 (1994)
The Use of Salicylaldehyde Phenylhydrazone as an Indicator for the Titration of Organometallic Reagents.
Brian E. Love et al.
The Journal of organic chemistry, 64(10), 3755-3756 (2001-10-25)
Junming Ho et al.
Journal of inorganic biochemistry, 119, 10-20 (2012-11-22)
A series of N,N-disubstituted salicylaldehyde semicarbazones (SSCs), HOC(6)H(4)CHN-NHCONR(2), and their rhenium(I) tricarbonyl complexes, [ReBr(CO)(3)(SSC)], have been synthesised and characterised by IR and (1)H NMR spectroscopy. Crystallographic analysis of the complex [ReBr(CO)(3)(H(2)Bu(2))] (H(2)Bu(2)=SSC where R=Bu(n)) showed that the SSC acts as...

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