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Sigma-Aldrich

5-Acetylsalicylamide

98%

Synonym(s):

5-Acetyl-2-hydroxybenzamide

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About This Item

Linear Formula:
CH3COC6H3(OH)CONH2
CAS Number:
Molecular Weight:
179.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

98%

mp

220-222 °C (lit.)

SMILES string

CC(=O)c1ccc(O)c(c1)C(N)=O

InChI

1S/C9H9NO3/c1-5(11)6-2-3-8(12)7(4-6)9(10)13/h2-4,12H,1H3,(H2,10,13)

InChI key

LWAQTCWTCCNHJR-UHFFFAOYSA-N

General description

5-Acetylsalicylamide is formed by lewis acidic ionic liquid catalyzed Friedel-Crafts acylation of salicylamide with acetyl chloride.

Application

5-Acetylsalicylamide can be used in the preparation of 5-acetyl-2(3H)-benzoxazolone, via two-step synthetic route using Hofmann rearrangement.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Acylation of salicylamide to 5-acetylsalicylamide using ionic liquids as dual catalyst and solvent.
Chen W, et al.
Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands), 16(5), 800-804 (2010)
New heterocyclic chalcones. Part 6. Synthesis and cytotoxic activities of 5-or 6-(3-aryl-2-propenoyl)-2 (3H)-benzoxazolones.
Ivanova YB, et al.
Heterocyclic Communications, 19(1), 23-28 (2013)

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