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Key Documents

S356

Sigma-Aldrich

Salicylaldehyde

reagent grade, 98%

Synonym(s):

2-Hydroxybenzaldehyde

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About This Item

Linear Formula:
2-(HO)C6H4CHO
CAS Number:
Molecular Weight:
122.12
Beilstein:
471388
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

Salicyladehyde (2-Hydroxybenzaldehyde) may be used in the preparation of pyrocatechol via Dakin reaction.
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.

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Mirta Rubčić et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(18), 5620-5631 (2012-03-27)
The Schiff base derived from salicylaldehyde and 2-amino-3-hydroxypyridine affords a diversity of solid forms, two polymorphic pairs of the enol-imino (D1 a and D1 b) and keto-amino (D2 a and D2 b) desmotropes. The isolated phases, identified by IR spectroscopy, X-ray crystallography, and (13)C

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