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| CAS No.: | 103-84-4 |
|---|---|
| Name: | Acetanilide |
| Article Data: | 1332 |
| Molecular Structure: | |
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|
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| 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 |
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| 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% |
| 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. |
| 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% |
| 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% |
| 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% |
| 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% |
| Conditions | Yield |
|---|---|
| With zinc diacetate for 2h; Heating; | 100% |
| In toluene for 24h; Yield given; |
| 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 |
| Conditions | Yield |
|---|---|
| With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 1h; | 100% |
| 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; |
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- Total:32 Page 1 of 1 1
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Consensus Reports
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. |