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346675

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
03812KY
02405CS
S04272

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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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