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103-84-4

Basic Information
CAS No.: 103-84-4
Name: Acetamide,N-phenyl-
Article Data: 1332
Cas Database
Molecular Structure:
Molecular Structure of 103-84-4 (Acetamide,N-phenyl-)
Formula: C8H9NO
Molecular Weight: 135.166
Synonyms: Acetanilide;Acetanilide(8CI);Acetamidobenzene;Acetanil;Acetylaniline;Antifebrin;Benzenamine, N-acetyl-;N-Acetylaminobenzene;N-Acetylaniline;N-Phenylacetamide;NSC 203231;NSC 7636;Phenalgene;Phenalgin;Antifebrin;acetamide, N-phenyl-;N-Acetylaniline;N-Phenylacetamid;N-phenylacetamide;N-Phénylacétamide;
EINECS: 203-150-7
Density: 1.103 g/cm3
Melting Point: 113-115 °C(lit.)
Boiling Point: 304.5 °C at 760 mmHg
Flash Point: 173.9 °C
Solubility: slightly soluble in water
Appearance: odourless solid chemical of leaf or flake-like appearance
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 22-26-36
Transport Information: N/A
PSA: 29.10000
LogP: 1.71800
Synthetic route
613-91-2

acetophenone oxime

103-84-4

Acetanilid

Conditions
ConditionsYield
With mesoporous silica chloride (SBA-Cl) In toluene for 3h; Beckmann rearrangement; Reflux;100%
trimethylsilylperrhenate; 3,5-bis-trifluromethylphenylboronic acid In acetonitrile at 120℃; for 4h; Product distribution / selectivity; Beckmann Rearrangement; Heating / reflux;99%
With p-toluenesulfonyl chloride; zinc(II) chloride In acetonitrile for 1h; Beckmann rearrangement; Inert atmosphere; Reflux;99%
103-88-8

4-bromoacetanilide

103-84-4

Acetanilid

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 4h;100%
With lithium Zersetzen des Reaktionsprodukts mit Wasser;
With calcium Zersetzen des Reaktionsprodukts mit Wasser;
With formic acid; C59H60N6O2Pt; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 12h; Inert atmosphere; Sealed tube; UV-irradiation;62 %Spectr.
108-24-7

acetic anhydride

98-95-3

nitrobenzene

103-84-4

Acetanilid

Conditions
ConditionsYield
With ammonium formate; titanium(IV) oxide; β‐cyclodextrin In water for 2.5h; Irradiation; Inert atmosphere;100%
Stage #1: nitrobenzene With sodium tetrahydroborate In water at 20℃; for 0.5h; Green chemistry;
Stage #2: acetic anhydride In water at 20℃; for 1.83333h; Catalytic behavior; Green chemistry;
99%
Stage #1: nitrobenzene With sodium tetrahydroborate; water In neat (no solvent) at 20℃; for 0.0166667h;
Stage #2: acetic anhydride In neat (no solvent) at 40℃; for 0.0333333h; Reagent/catalyst; Solvent;
97%
108-24-7

acetic anhydride

62-53-3

aniline

103-84-4

Acetanilid

Conditions
ConditionsYield
With pyridine; aluminum oxide at 93 - 95℃; for 1h; microwave irradiation;100%
In dichloromethane at 20℃; Inert atmosphere;100%
In dichloromethane at 21℃; Inert atmosphere;100%
64-19-7

acetic acid

62-53-3

aniline

103-84-4

Acetanilid

Conditions
ConditionsYield
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With zinc(II) oxide for 2.33h; Reflux; chemoselective reaction;99%
60-35-5

acetamide

591-50-4

iodobenzene

103-84-4

Acetanilid

Conditions
ConditionsYield
With acetamide; potassium phosphate; CuI In dodecane; ethyl acetate; toluene100%
With potassium phosphate; copper(l) iodide; L-arginine In 1,4-dioxane at 100℃; for 24h; Goldberg reaction;99%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In toluene at 110℃; for 5h;97%
103-71-9

phenyl isocyanate

64-19-7

acetic acid

103-84-4

Acetanilid

Conditions
ConditionsYield
With zinc diacetate for 2h; Heating;100%
In toluene for 24h; Yield given;
5326-87-4

N-(phenyl)bromoacetamide

103-84-4

Acetanilid

Conditions
ConditionsYield
With indium; acetic acid In methanol at 20℃; for 1h;100%
With nickel In isopropyl alcohol for 20h; Heating;81%
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In toluene for 14h; Heating;81%
Multi-step reaction with 2 steps
1: 64 percent / NaBH4, 5percent aq. NaOH / ethanol
2: 24 percent / lithium 2-thienyltellurolate / tetrahydrofuran / 0.5 h
View Scheme
539-03-7

N-(4-chlorophenyl)acetamide

103-84-4

Acetanilid

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 1h;100%
60-35-5

acetamide

108-90-7

chlorobenzene

103-84-4

Acetanilid

Conditions
ConditionsYield
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 95℃; for 18h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Time; Inert atmosphere; Sonication;99.1%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; potassium carbonate In 1,4-dioxane at 90℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox;80%
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 48h; Ullmann condensation;33%
With copper(l) iodide; potassium carbonate; pipecolic Acid In N,N-dimethyl-formamide at 110℃; for 30h; Goldberg coupling reaction;24%
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 95℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Sonication;
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Consensus Reports

ACETANILIDE is reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The Acetanilide, with the CAS registry number 103-84-4 and EINECS registry number 203-150-7, has the systematic name of N-phenylacetamide, and it is also known as Antifebrin. It is an odourless solid chemical of leaf or flake-like appearance, and the pure crystals are plate shaped and colorless to white. It is slightly soluble in water, and stable under most conditions. The molecular formula of this chemical is C8H9NO.

The physical properties of Acetanilide are as followings: (1)ACD/LogP: 1.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.08; (4)ACD/LogD (pH 7.4): 1.08; (5)ACD/BCF (pH 5.5): 3.91; (6)ACD/BCF (pH 7.4): 3.91; (7)ACD/KOC (pH 5.5): 92.44; (8)ACD/KOC (pH 7.4): 92.44; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 20.31 Å2; (13)Index of Refraction: 1.575; (14)Molar Refractivity: 40.52 cm3; (15)Molar Volume: 122.5 cm3; (16)Polarizability: 16.06×10-24cm3; (17)Surface Tension: 41.5 dyne/cm; (18)Density: 1.103 g/cm3; (19)Flash Point: 173.9 °C; (20)Enthalpy of Vaporization: 54.49 kJ/mol; (21)Boiling Point: 304.5 °C at 760 mmHg; (22)Vapour Pressure: 0.000871 mmHg at 25°C.

Preparation of Acetanilide: It can be prepared by reacting acetic anhydride with aniline: 
C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOH

Applictions of Acetanilide: It is often used as an inhibitor in hydrogen peroxide to stabilize cellulose ester varnishes. It is also used in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, camphor synthesis and so on. It is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs as well. What's more, it is also a precursor in the synthesis of penicillin and other pharmaceuticals.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin, and it is also harmful if swallowed. Therefore, you had better take the following instructions: Do not breathe dust; Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
 
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Nc1ccccc1)C
(2)InChI: InChI=1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
(3)InChIKey: FZERHIULMFGESH-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 8500ug/kg (8.5mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 30, Pg. 91, 1941.
cat LDLo oral 250mg/kg (250mg/kg)   Journal of the American Pharmaceutical Association. Vol. 28, Pg. 70, 1939.
dog LDLo intravenous 300mg/kg (300mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1290, 1935.
dog LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1290, 1935.
guinea pig LDLo oral 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1290, 1935.
human TDLo oral 14mg/kg/D (14mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 62, 1969.
man LDLo oral 56mg/kg/H-I (56mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
American Journal of the Medical Sciences. Vol. 122, Pg. 770, 1901.
man LDLo unreported 59mg/kg (59mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 405mg/kg (405mg/kg) BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
JAMA, Journal of the American Medical Association. Vol. 12, Pg. 103, 1889.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 1210mg/kg (1210mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 20, 1971.
rabbit LDLo oral 1500mg/kg (1500mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 466, 1933.
rat LD50 intraperitoneal 540mg/kg (540mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 48, Pg. 204, 1959.
rat LD50 oral 800mg/kg (800mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 54, Pg. 159, 1935.

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