CAS No.103-84-4,Acetanilide Suppliers

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Basic Information

Molecular Structure:
CAS No.:	103-84-4
Name:	Acetanilide
Article Data:	1332

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:	Xn
Risk Codes:	22-36/37/38
Safety:	22-26-36
PSA:	29.10000
LogP:	1.71800

Synthetic route

: 613-91-2
acetophenone oxime

: 103-84-4
Acetanilid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With acetamide; potassium phosphate; CuI In dodecane; ethyl acetate; toluene	100%
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

Conditions	Yield
With zinc diacetate for 2h; Heating;	100%
In toluene for 24h; Yield given;

: 5326-87-4
N-(phenyl)bromoacetamide

: 103-84-4
Acetanilid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

Raw Materials

111-72-8

64-19-7

26060-56-0

Downstream Products

588-46-5

80-08-0

23776-98-9

1948-04-5

525-76-8

91-49-6

1975-96-8

540-37-4

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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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