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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:
40187-51-7
Molecular Weight:
179.17
EC Number:
254-830-5
MDL number:
MFCD00049222
UNSPSC Code:
12352100
PubChem Substance ID:
24861425

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
GHS07

Signal Word

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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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