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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:
90-02-8
Molecular Weight:
122.12
Beilstein:
471388
MDL number:
MFCD00003317
UNSPSC Code:
12352100
PubChem Substance ID:
24899563
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

H302,H315,H319,H341,H411

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)

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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)
Eagleson M.
Concise Encyclopedia Chemistry, 301-301 (1994)
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)
Wen-Yong Han et al.
Organic letters, 14(4), 976-979 (2012-02-02)
The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids with a newly designed thiourea-binol catalyst is presented. A broad range of alkylaminophenols can be obtained in good yield (up to 92%) and good to high enantioselectivity (up
View All Related Papers

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