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397237

Sigma-Aldrich

Acetanilide

zone-refined, purified by sublimation, ≥99.95%

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Synonym(s):
N-Phenylacetamide
Linear Formula:
CH3CONHC6H5
CAS Number:
Molecular Weight:
135.16
Beilstein:
606468
EC Number:
MDL number:
eCl@ss:
39031308
PubChem Substance ID:
NACRES:
NA.22

grade

zone-refined

Quality Level

vapor density

4.65 (vs air)

vapor pressure

1 mmHg ( 114 °C)

Assay

≥99.95%

form

solid

autoignition temp.

1004 °F

purified by

sublimation

bp

304 °C (lit.)

mp

113-115 °C (lit.)

SMILES string

CC(=O)Nc1ccccc1

InChI

1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

InChI key

FZERHIULMFGESH-UHFFFAOYSA-N

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This Item
112933PHR1086PHR1530
Acetanilide zone-refined, purified by sublimation, ≥99.95%

397237

Acetanilide

Acetanilide 99%

112933

Acetanilide

Acetaminophen Related Compound D Pharmaceutical Secondary Standard; Certified Reference Material

PHR1530

Acetaminophen Related Compound D

bp

304 °C (lit.)

bp

304 °C (lit.)

bp

304 °C (lit.)

bp

304 °C (lit.)

form

solid

form

solid

form

-

form

-

mp

113-115 °C (lit.)

mp

113-115 °C (lit.)

mp

~Approximately 115 °C, 113-115 °C (lit.)

mp

113-115 °C (lit.)

grade

zone-refined

grade

-

grade

certified reference material, pharmaceutical secondary standard

grade

certified reference material, pharmaceutical secondary standard

vapor density

4.65 (vs air)

vapor density

4.65 (vs air)

vapor density

4.65 (vs air)

vapor density

4.65 (vs air)

General description

Acetanilide is an aniline derivative. Crystal structure of acetanillide has been studied by X-ray diffraction. It crystallizes in orthorhombic system having space group of Pbca. Its photolysis has been studied in the presence of β-cyclodextrin (cycloheptaamylose). Aminoacetophenone derivatives are obtained by the Fries rearrangement of acetanilide in the presence zeolites Y and β.

Application

Acetanilide may be used in the synthesis of ortho-haloacetanilides via regioselective C-H functionalization/halogenation reaction in the presence of Pd(OAc)2 and Cu(OAc)2 catalyst. It may be used in the preparation of chlorosubstituted acetanilides.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

321.8 °F - closed cup

Flash Point(C)

161 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Oxidative Chlorination of Acetanilides by Metal Chlorides-Hydrogen Peroxide in Acid-Aqueous Medium Systems.
Jerzy G and Slawomir G.
Synthetic Communications, 27(18), 3291-3299 (1997)
The crystal structure of acetanilide.
Brown CJ and Corbridge DEC.
Acta Crystallographica, 7(11), 711-715 (1954)
Fries rearrangement of acetanilide over zeolite catalysts.
Balkus Jr KJ, et al.
J. Mol. Catal. A: Chem., 134(1), 137-143 (1998)
A REMPI and ZEKE Spectroscopic Study of trans-Acetanilide? H2O and Comparison to Ab Initio CASSCF Calculations.
Ullrich S and Muller-Dethlefs K.
The Journal of Physical Chemistry A, 106(40), 9188-9195 (2002)
Photochemical rearrangement of acetanilide, benzanilide, and ethyl phenyl carbonate in the presence of β-cyclodextrin.
Chenevert R and Plante R.
Canadian Journal of Chemistry, 61(6), 1092-1095 (1983)

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